Drug Reference for FDA Approved Psychiatric Drugs @ Neurotransmitter.net


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Attention Valued Visitor: A Drug Reference Page for FDA Approved General Anesthetics is now available!
Shawn Thomas (Shawn@neurotransmitter.net) is working to summarize the mechanisms of action of every drug approved by the FDA for a brain- related condition. In addition, new pages with more automated content will soon replace some of the older pages on the web site. If you have suggestions about content that you would like to see, e-mail Shawn@neurotransmitter.net if you have anything at all to share.


Generic Name:
alprazolam

Trade Name:
Xanax ® [Pfizer]

IUPAC Name:
8-chloro-6-cyclohexyl-1-methyl-
4H-[1,2,4]triazolo[4,3-
a][1,4]benzodiazepine

Dosage Forms/Routes:
Tablet/oral;
Tablet/orally disintegrating;
Extended release tablet/oral;
Concentrate/oral

Major Metabolites:
4-hydroxyalprazolam;
a-hydroxyalprazolam

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
10/16/1981


Manufacturers:

[FDA Search]

Product Insert:
[Tablet]
[XR Tablet]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C17H13ClN4

Molecular Mass:
308.765 g/mol

Indications:
Anxiety disorder; Generalized Anxiety Disorder (GAD); panic disorder

Possible Mechanism of Action:
Alprazolam is a nonselective benzodiazepine agonist (12).

Chemical Class:
triazolo analog of the 1,4 benzodiazepine class

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link]

Generic Name:
amitriptyline hydrochloride

Common Chemical Name:
3-(10,11-dihydro-5H-dibenzo
[a,d] cycloheptene-5-
ylidene)-N,N-dimethyl-1-
propanamine hydrochloride

Dosage Forms/Routes:
Tablet/oral


Major Metabolites:
nortriptyline;
10-hydroxyamitriptyline;
10-hydroxynortriptyline

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
04/07/1961

Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C20H24ClN

Molecular Mass:
313.864 g/mol

Indications:
Major Depressive Disorder

Possible Mechanisms of Action:
Amitriptyline inhibits the reuptake of both serotonin and norepinephrine (1). Amitriptyline acts as an antagonist at all subtypes of muscarinic acetylcholine receptors (2). The drug also has antagonist activity at histamine H1 and H2 receptors, serotonin 5-HT2A receptors, and norepinephrine alpha-1 receptors (1). It also binds to histamine H4 receptors (11).

Chemical Class:
tertiary tricyclic (dibenzocycloheptadine derivative)

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link]  

Generic Name:
amitriptyline hydrochloride and
chlordiazepoxide

Trade Name:
Limbitrol ® [Valeant]

Dosage Forms/Routes:
Tablet/oral

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]

Initial Approval:
12/23/1977


Manufacturers:

[FDA Search]

Product Insert:
[Link]

Epocrates:
[Link]

Empirical Formula:
C36H37ClN4O

Molecular Mass:
613.619 g/mol

Indications:
Moderate to severe depression associated with moderate to severe anxiety
Possible Mechanisms of Action:
Please refer to the entries for amitriptyline hydrochloride and chlordiazepoxide.
PubChem 2D Structure:

Generic Name:
amitriptyline hydrochloride and
perphenazine

Dosage Forms/Routes:
Tablet/oral

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]

Initial Approval:
08/23/1965


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C41H50Cl2N4OS

Molecular Mass:
717.833 g/mol

Indications:
Treatment of patients with moderate to severe anxiety and/or agitation and depressed mood; patients with depression in whom anxiety and/or agitation are moderate or severe; patients with anxiety and depression associated with chronic physical disease; patients in whom depression and anxiety cannot be clearly differentiated; schizophrenic patients who have associated symptoms of depression
Possible Mechanisms of Action:
Please refer to the entries for amitriptyline hydrochloride and perphenazine.
PubChem 2D Structure:

Generic Name:
amoxapine

Common Chemical Name:

2-chloro-11-(1-piperazinyldibenz-
[b,f][1,4]oxapine

Dosage Forms/Routes:
Tablet/oral


Major Metabolites:
8-hydroxyamoxapine;
7-hydroxyamoxapine

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
09/22/1980


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C17H16ClN3O

Molecular Mass:
313.781 g/mol

Indications:
Depression in patients with neurotic or reactive depressive disorders as well as endogenous and psychotic depressions; depression accompanied by anxiety or agitation
Possible Mechanisms of Action:
Amoxapine inhibits the reuptake of norepinephrine (5). The drug also inhibits glycine reuptake mediated by glycine transporter 2a (GLYT2a) (6). Amoxapine is an antagonist at serotonin 5-HT2A (7) and 5-HT2C receptors (7, 8). In addition, amoxapine is an antagonist at dopamine D2 receptors (9). It may also be an antagonist at alpha-1-adrenoceptors (130), histamine H1 receptors (130), and dopamine D4 receptors (9, 10). Finally, amoxapine binds with moderate affinity to alpha-2-adrenoceptors and binds with very low affinity to muscarinic acetylcholine receptors (131).
Chemical Class:
tricyclic dibenzoxazepine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link]  

Generic Name:
aripiprazole

Trade Name:
Abilify ® [
Bristol-Myers Squibb/Otsuka]

IUPAC Name:
7-[4-[4-(2,3-dichlorophenyl)
piperazin-1-yl]butoxy]-3,4-
dihydro-1H-quinolin-2-one

Dosage Forms/Routes:
Tablet/oral;
Solution/oral;
Tablet/orally disintegrating;

Injectable/intramuscular

Major Metabolites:
dehydro-aripiprazole

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
11/15/2002 


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C23H27Cl2N3O2

Molecular Mass:
448.385 g/mol

Indications:
Schizophrenia; acute manic and mixed episodes associated with bipolar disorder

Possible Mechanisms of Action:
Depending on the cell type and function examined, aripiprazole is an agonist, partial agonist, or antagonist at dopamine D2 receptors (13). The drug is a partial agonist at dopamine D3 receptors (13). In addition, it is a partial agonist at serotonin 5-HT1A and 5-HT2A receptors and an inverse agonist at serotonin 5-HT2B receptors (13). Aripiprazole also exhibits significant affinity for serotonin 5-HT7 receptors, alpha-1A-adrenoceptors, and histamine H1 receptors (13).

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
atomoxetine hydrochloride

Trade Name:
Strattera ® [Eli Lilly]

IUPAC Name:
N-methyl-3-(2-methylphenoxy)-
3-phenyl-propan-1-amine hydrochloride

Dosage Forms/Routes:
Capsule/oral

Major Metabolites:
4-hydroxyatomoxetine;
N-desmethylatomoxetine

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
11/26/2002


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C17H22ClNO

Molecular Mass:
291.815 g/mol

Indications:
ADHD
Possible Mechanisms of Action:
Atomoxetine is a selective norepinephrine reuptake inhibitor (SNRI) (3). A major metabolite of atomoxetine, 4-hydroxyatomoxetine, is a partial agonist at kappa opioid receptors (4).

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
bupropion hydrochloride

Trade Name:
Wellbutrin ®, Zyban® [
GlaxoSmithKline]

IUPAC Name:
1-(3-chlorophenyl)-2-tert-
butylamino-propan-1-one
hydrochloride

Dosage Forms/Routes:
Tablet/oral;
Extended release tablet/oral

Major Metabolites:
hydroxybupropion; threohydrobupropion; erythrohydrobupropion

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
12/30/1985


Manufacturers:

[FDA Search]

Product Insert:
[Tablet]
[SR]
[XL]
[Zyban]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C13H19Cl2NO

Molecular Mass:
276.202 g/mol

Indications:
Major depressive disorder; smoking cessation aid

Possible Mechanisms of Action:
Bupropion inhibits the norepinephrine and dopamine transporters with low potency (14). A metabolite of bupropion, hydroxybupropion, contributes to the drug's effects as a norepinephrine and dopamine reuptake inhibitor (14). The (2S,3S)- isomer of hydroxybupropion is a much more potent norepinephrine reuptake inhibitor than bupropion. Other bupropion metabolites may also contribute to the drug's effects at the norepinephrine and dopamine transporters (14). Bupropion is a noncompetitive antagonist at nicotinic acetylcholine receptors including the alpha3beta2, alpha4beta2, alpha3beta4, and alpha4beta4 subtypes (14, 15). Bupropion metabolites such as (2S,3S)-hydroxybupropion are also antagonists at nicotinic acetylcholine receptors (14).

Chemical Class:
aminoketone

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link]  

Generic Name:
buspirone hydrochloride

Trade Name:
BuSpar ® [
Bristol-Myers Squibb]

IUPAC Name:
8-[4-(4-pyrimidin-2-
ylpiperazin-1-yl)butyl]-8-
azaspiro[4.5]decane-7,9-
dione hydrochloride

Dosage Forms/Routes:
Tablet/oral


Major Metabolites:
1-pyrimidinylpiperazine

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
09/29/1986


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C21H32ClN5O2

Molecular Mass:
421.964 g/mol

Indications:
Anxiety disorders or short-term relief of the symptoms of anxiety
Possible Mechanisms of Action:
Buspirone is a partial agonist at serotonin 5-HT1A receptors (17). It also acts as an antagonist at dopamine D2 receptors, but its affinity for these receptors is 16-fold weaker than its affinity for 5-HT1A receptors (18).

Chemical Class:
piperazinyl derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
chlordiazepoxide hydrochloride

Trade Name:
Librium ® [Valeant]

Common Chemical Name:
9-chloro-5-hydroxy-N-methyl-
6- phenyl-2,5-
diazabicyclo[5.4.0]undeca-
1,6,8,10-tetraen-3-imine
hydrochloride

Dosage Forms/Routes:
Capsule/oral

Major Metabolites:
desmethylchlordiazepoxide;
demoxepam;
desmethyldiazepam;
oxazepam

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
02/24/1960


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C16H15Cl2N3O

Molecular Mass:
336.215 g/mol

Indications:
Anxiety disorders or short-term relief of the symptoms of anxiety; withdrawal symptoms of acute alcoholism; preoperative apprehension and anxiety
Possible Mechanism of Action:
Chlordiazepoxide is a nonselective benzodiazepine agonist (19, 20).

Chemical Class:
2-keto benzodiazepine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
chlorpromazine hydrochloride

Trade Name:
Thorazine ® [
GlaxoSmithKline]

IUPAC Name:
3-(2-chlorophenothiazin-10-
yl)- N,N-dimethyl-propan-1-
amine hydrochloride

Dosage Forms/Routes:
Tablet/oral;
Injectable/injection;
Syrup/oral;
Concentrate/oral

Major Metabolites:
7-hydroxychlorpromazine;
3-hydroxychlorpromazine;
chlorpromazine N-oxide; chlorpromazine sulfoxide; norchlorpromazine; norchlorpromazine sulfoxide

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
11/20/1957


Manufacturers:

[FDA Search]

Product Insert:
[Tablet]
[Injectable]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C17H19ClN2S

Molecular Mass:
318.865 g/mol

Indications:
Schizophrenia; nausea and vomiting; relief of restlessness and apprehension before suregery; acute intermittent porphyria; adjunct in the treatment of tetanus; manic episodes associated with bipolar disorder; relief of intractable hiccups; for the treatment of severe behavioral problems in children (1 to 12 years of age) marked by combativeness and/or explosive hyperexcitable behavior (out of proportion to immediate provocations), and in the short-term treatment of hyperactive children who show excessive motor activity with accompanying conduct disorders consisting of some or all of the following symptoms: impulsivity, difficulty sustaining attention, aggressivity, mood lability and poor frustration tolerance

Possible Mechanisms of Action:
Chlorpromazine is an antagonist at dopamine D1 and D2 receptors (21) as well as D3 (22) and D4 receptors (23). The drug may be an inverse agonist at dopamine D2S receptors (133).
It also exhibits antagonist activity at serotonin 5-HT2A and 5-HT2C receptors (24). In addition, chlorpromazine is an antagonist at alpha-1A-adrenoceptors (25), alpha-1B-adrenoceptors (25), alpha-2B-adrenoceptors (26), alpha-2C-adrenoceptors (26), and histamine H1 receptors (27). The drug also binds with moderately high affinity to muscarinic M1, M3, M4, and M5 receptors (28). Finally, chlorpromazine binds with high affinity to serotonin 5-HT6 and 5-HT7 receptors (29).

Chemical Class:
aliphatic phenothiazine


PubChem 2D Structure:


"3D" Structure (Requires Chime):
[Link]

Generic Name:
citalopram hydrobromide

Trade Name:
Celexa ® [
Forest Labs]

IUPAC Name:
1-(3-dimethylaminopropyl)-1-
(4-fluorophenyl)-3H-
isobenzofuran-5-carbonitrile
hydrobromide

Dosage Forms/Routes:
Tablet/oral;
Tablet/orally disintegrating;
Solution/oral

Major Metabolites:
demethylcitalopram; didemethylcitalopram;
citalopram-N-oxide

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
07/17/1998


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C20H22BrFN2O

Molecular Mass:
405.304 g/mol

Indications:
Major depressive disorder

Possible Mechanism of Action:
Citalopram is a selective serotonin reuptake inhibitor (SSRI) (16).

Chemical Class:
racemic bicyclic phthalane derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link]

Generic Name:
clomipramine hydrochloride

Trade Name:
Anafranil ® [
Tyco Healthcare]

Common Chemical Name:
3-chloro-5-[3-
(dimethylamino)propyl]-10,11-
dihydro-5H-dibenz[b,f]azepine
monohydrochloride

Dosage Forms/Routes:
Capsule/oral

Major Metabolites:
desmethylclomipramine;
8-hydroxyclomipramine;

8-hydroxydesmethylclomipramine

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
12/29/1989


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C19H24Cl2N2

Molecular Mass:
351.313 g/mol

Indications:
OCD in adults, children, and adolescents

Possible Mechanisms of Action:
Clomipramine inhibits the reuptake of both serotonin and norepinephrine (30). The drug also binds to serotonin 5-HT2A, 5-HT2C, and 5-HT3 receptors, dopamine D2 and D3 receptors, and alpha-1-adrenoceptors (30). Clomipramine acts as an antagonist at muscarinic acetylcholine receptors (31), but the muscarinic receptor subtypes that it affects have not been identified. The drug is also an antagonist at histamine H1 receptors (32). Finally, clomipramine binds to serotonin 5-HT6 receptors (116).

Chemical Class:
dibenzazepine


PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link]

Generic Name:
clonazepam

Trade Name:
Klonopin ® [
Roche]

IUPAC Name:
6-(2-chlorophenyl)-9-nitro-
2,5-diazabicyclo[5.4.0]undeca-
5,8,10,12-tetraen-3-one

Dosage Forms/Routes:
Tablet/oral;
Tablet/orally disintegrating

Major Metabolite:
7-aminoclonazepam

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
06/04/1975


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula: C15H10ClN3O3

Molecular Mass:
315.711 g/mol

Indications:
Panic disorder; alone or as an adjunct in the treatment of the Lennox-Gastaut syndrome (petit mal variant), akinetic seizures, and myoclonic seizures; in patients with absence seizures (petit mal) who have failed to respond to succinimides, clonazepam may be useful

Possible Mechanism of Action:
Clonazepam is a nonselective benzodiazepine agonist (12).

Chemical Class:
3-hydroxy benzodiazepine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
clorazepate dipotassium

Trade Name:
Tranxene ® [Ovation]

IUPAC Name:
dipotassium 9-chloro-3-oxo-6-
phenyl-2,5-
diazabicyclo[5.4.0]undeca-
5,8,10,12-tetraene-4-carboxylic
acid hydroxide

Dosage Forms/Routes:
Tablet/oral;
Capsule/oral

Major Metabolites:
nordiazepam;
oxazepam

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
06/23/1972


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C16H12ClK2N2O4+

Molecular Mass:
409.927 g/mol

Indications:
Anxiety disorders or short-term relief of the symptoms of anxiety; adjunctive therapy in the management of partial seizures; withdrawal symptoms of acute alcoholism
Possible Mechanism of Action:
Clorazepate is a nonselective benzodiazepine agonist (33).

Chemical Class:
2-keto benzodiazepine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
clozapine

Trade Name:
Clozaril ® [
Novartis]

Common Chemical Name:
8-chloro-11-(4-methyl-1-
piperazinyl)-5H-dibenzo [b,e]
[1,4] diazepine

Dosage Forms/Routes:
Tablet/oral;
Tablet/orally disintegrating

Major Metabolite:
N-desmethylclozapine;
clozapine N-oxide

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
09/26/1989 


Manufacturers:

[FDA Search]

Product Insert:
[Clozaril tablet]
[Orally disintegrating tablet]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C18H19ClN4

Molecular Mass:
326.823 g/mol

Indications:
Treatment-resistant schizophrenia; reduction in the risk of recurrent suicidal behavior in schizophrenia or schizoaffective disorders

Possible Mechanisms of Action: Clozapine is a low affinity inverse agonist at dopamine D2S receptors (106, 133) and a high affinity antagonist at D4 receptors (34). It is also an antagonist at serotonin 5-HT2A (35), 5-HT2B (36), and 5-HT6 receptors (37). Clozapine is an inverse agonist at serotonin 5-HT2C (38) and 5-HT7 receptors (39). The drug is an antagonist at alpha-1A-adrenoceptors and alpha-1B-adrenoceptors (25). Clozapine is also an antagonist at alpha-2A-adrenoceptors and alpha-2C-adrenoceptors (40). Clozapine binds with relatively high affinity to alpha-2B-adrenoceptors (41); it likely acts as an antagonist at these receptors. Depending on cell type and receptor density, clozapine is an antagonist or partial agonist at muscarinic M1, M2, M3, and M4 receptors (42, 43). The drug is also an antagonist at muscarinic M5 receptors (44). Finally, clozapine is an antagonist at histamine H1 receptors (27).

Chemical Class:
tricyclic dibenzodiazepine derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
desipramine hydrochloride

Trade Name:
Norpramin ® [
Sanofi-Aventis]

Common Chemical Name:
5 H -Dibenz[ bf ]azepine-5-
propanamine, 10,11-dihydro-
N-methyl-, monohydrochloride

Dosage Forms/Routes:
Tablet/oral

Major Metabolite:
2-hydroxydesipramine

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
11/20/1964


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C18H23ClN2

Molecular Mass:
302.841 g/mol

Indications:
Various depressive syndromes, especially endogenous depression
Possible Mechanisms of Action:
Desipramine is a high affinity norepinephrine reuptake inhibitor (45). It exhibits relatively low affinity for histamine H1 receptors, muscarinic acetylcholine receptors, and alpha-1-adrenoceptors (45).

Chemical Class:
secondary tricyclic dibenzazepine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
desvenlafaxine succinate

Trade Name:
Pristiq ® [
Wyeth]

IUPAC Name:
butanedioic acid; 4-[2-dimethylamino-1-(1-
hydroxycyclohexyl)ethyl]phenol; hydrate

Dosage Forms/Routes:
Extended release tablet/oral

Major Metabolite:
desvenlafaxine
glucoronide

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
02/29/2008


Manufacturers:

[FDA Search]

Product Insert:
[Link]

Empirical Formula:
C20H33NO7

Molecular Mass:
399.47852 g/mol

Indications:
Major depressive disorder

Possible Mechanisms of Action:
Desvenlafaxine inhibits the reuptake of serotonin and norepinephrine (154). It has a greater affinity for the serotonin transporter (154).

Chemical Class:
the succinate salt of the isolated major active metabolite of venlafaxine, a phenethylamine bicyclic derivative

PubChem 2D Structure:

Generic Name:
dexmethylphenidate hydrochloride

Trade Name:
Focalin ® [
Novartis]

Common Chemical Name:
alpha-phenyl-2-piperidineacetate
hydrochloride, (R,R’)-(+)-

Dosage Forms/Routes:
Tablet/oral;
Extended release capsule/oral

Major Metabolite:
d-ritalinic acid

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
11/13/2001


Manufacturers:

[FDA Search]

Product Insert:
[Focalin Tablet]
[Focalin XR Capsule]

Epocrates:
[Link]

Empirical Formula:
C14H19NO2•HCl

Molecular Mass:
269.77 g/mol

Indications:
ADHD
Possible Mechanisms of Action:
Dexmethylphenidate inhibits the dopamine transporter and, to a lesser degree, the norepinephrine transporter (46). The drug offers a better therapeutic index than racemic threo-methylphenidate hydrochloride (Ritalin®) (47).

Chemical Class:
d-threo enantiomer of racemic methylphenidate hydrocholoride

2D Structure:

Generic Name:
dextroamphetamine sulfate

Trade Name:
Dexedrine ® [
GlaxoSmithKline]

IUPAC Name:
1-phenylpropan-2-amine;
sulfuric acid

Dosage Forms/Routes:
Tablet/oral;
Extended release capsule/oral;
Solution/oral

Major Metabolites:
p-hydroxyamphetamine;
p-hydroxynorephedrine

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]


Initial Approval:
02/26/1976


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C18H28N2O4S

Molecular Mass:
368.492 g/mol

Indications:
ADHD; narcolepsy

Possible Mechanisms of Action:
At plasmalemmal catecholamine transporters, amphetamine indirectly increases the efflux of cytosolic catecholamines so that they are released into the synaptic cleft (144). The drug causes the release of norepinephrine more potently than it causes the release of dopamine; it is much less effective as a serotonin releasing agent (144) The drug also directly inhibits norepinephrine and dopamine reuptake at higher concentrations (144). Amphetamine- induced activation of protein kinase C (PKC) beta(II) is likely to be responsible for the drug's effect on dopamine efflux (145). Na+ is cotransported with amphetamine as it enters neurons via catecholamine transporters; amphetamine-induced increases in intracellular Na+ may stimulate Na+/Ca2+ antiporters, resulting in an influx of Ca2+ into the cytosol (146). The activity of a Ca2+ dependent enzyme, phospholipase C (PLC), is increased by amphetamine, and PLC may be responsible for the increase in PKC beta(II) activity associated with amphetamine (146). Intracellular dopamine is also required for amphetamine- induced increases in PKC activity (146). Amphetamine increases the activity of phospholipase A2 (PLA2), perhaps by increasing intracellular pH (146). Low PLA2 activity may increase the activation of PKC, while high PLA2 activity may decrease the activation of PKC by amphetamine (146).

Amphetamine, a weak base, increases cytosolic dopamine and norepinephrine through two mechanisms. First, amphetamine inhibits vesicular sequestration of dopamine and norepinephrine into vesicles by directly interacting with vesicular monoamine transporter-2 (VMAT-2) (147). Second, amphetamine decreases VMAT-2 activity by reducing the pH gradients that drive monoamine uptake into vesicles (148).

At higher concentrations, amphetamine may act as a competitive antagonist at NMDA receptors (149). In addition, the drug is an agonist at TA1, a trace amine receptor (150).

Chemical Class:
dextro isomer of d,l-amphetamine sulfate

PubChem 2D Structure:


"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
diazepam

Trade Name:
Valium ® [
Roche]

IUPAC Name:
9-chloro-2-methyl-6-phenyl-
2,5-diazabicyclo[5.4.0]undeca-
5,8,10,12-tetraen-3-one

Dosage Forms/Routes:
Tablet/oral;
Injectable/injection;
Concentrate/oral;
Gel/rectal

Major Metabolites:
nordiazepam;
temazepam;
oxazepam

Database Search Links:
[PubMed]

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[PDSP Ki database]

Initial Approval:
11/15/1963 


Manufacturers:

[FDA Search]

Product Insert:
[Valium Tablet]
[Injectable]
[Gel]
[Concentrate]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C16H13ClN2O

Molecular Mass:
284.74 g/mol

Indications:
Anxiety disorders or short-term relief of the symptoms of anxiety; symptomatic relief of acute alcohol withdrawal; adjunct for the relief of skeletal muscle spasm due to reflex spasm to local pathology, spasticity caused by upper motor neuron disorders, athetosis, and stiff-man syndrome; adjunct for convulsive disorders
Possible Mechanisms of Action:
Diazepam is a nonselective benzodiazepine agonist (12). Diazepam is also an agonist at peripheral benzodiazepine receptors (48).

Chemical Class:
2-keto benzodiazepine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
divalproex sodium

Trade Name:
Depakote ® [
Abbott Labs]

IUPAC Name:
sodium; 2-propylpentanoate;
2-propylpentanoic acid

Dosage Forms/Routes:
Tablet (delayed release)/oral;
Capsule (delayed release pellets)/oral;
Tablet (extended release)/oral

Major Metabolites:
3-keto-valproic acid;
trans-2-ene valproic acid; valproic acid glucuronide

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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PubChem]
[PDSP Ki database]

Initial Approval:
03/10/1983


Manufacturers:

[FDA Search]

Product Insert:
[Depakote Capsule]
[Depakote Tablet]
[Depakote ER Tablet]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C16H31NaO4

Molecular Mass:
310.405 g/mol

Indications:
Depakote ER Only: Manic episodes associated with bipolar disorder; prophylaxis of migraine headaches

All dosage forms: Monotherapy and adjunctive therapy in the treatment of patients with complex partial seizures that occur either in isolation or in association with other types of seizures; sole or adjunctive therapy in the treatment of simple and complex absence seizures; adjunct for the treatment of patients with multiple seizure types that include absence seizures

Possible Mechanisms of Action:
Divalproex is a histone deacetylase inhibitor (49). The enhancement of gamma-aminobutyric acid (GABA) activity by divalproex is possibly due to the downregulation of GAT-1 and GAT-3 GABA transporter proteins by the drug (50); the cause of this effect is currently unknown. Divalproex also inhibits succinate semialdehyde dehydrogenase (153). At voltage-gated sodium channnels, divalproex shifts the voltage dependence of steady-state inactivation to more hyperpolarized potentials (51); the degree to which this action occurs at therapeutically relevant concentrations in humans is currently not known (52). Finally, divalproex may inhibit T-type calcium channels (53).

Chemical Class:
carboxylic acid derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
doxepin hydrochloride

Trade Name:
Sinequan ® [
Pfizer]

Common Chemical Name:
1-Propanamine, 3-
dibenz[b,e]oxepin-
11(6H)ylidene-N,N-dimethyl-,
hydrochloride

Dosage Forms/Routes:
Capsule/oral;
Concentrate/oral;
Cream/topical

Major Metabolite:
desmethyldoxepin

Database Search Links:
[PubMed]

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PubChem]
[PDSP Ki database]

Initial Approval:
09/23/1969


Manufacturers:

[FDA Search]

Product Insert:
[Sinequan Capsule and Concentrate]
[Zonalon Cream]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C19H22ClNO

Molecular Mass:
315.837 g/mol

Indications:
Psychoneurotic patients with depression and/or anxiety; depression and/or anxiety associated with alcoholism (not to be taken concomitantly with alcohol); depression and/or anxiety associated with organic disease; psychotic depressive disorders with associated anxiety including involutional depression and bipolar disorders

Possible Mechanisms of Action:
Doxepin weakly inhibits the reuptake of norepinephrine (54, 130) and serotonin (55, 130). It is a potent antagonist at histamine H1 (56, 57) and H2 receptors (57). Doxepin is also an antagonist at alpha-1-adrenoceptors (56). The drug binds to both serotonin 5-HT2A and 5-HT2C receptors (7). In addition, it is an antagonist at all subtypes of muscarinic acetylcholine receptors (58).

Chemical Class:
dibenzoxepin derivative (tertiary tricyclic)

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
duloxetine hydrochloride

Trade Name:
Cymbalta ® [
Eli Lilly]

IUPAC Name:
N-methyl-3-naphthalen-1-
yloxy-3-thiophen-2-yl-propan-
1-amine hydrochloride

Dosage Forms/Routes:
Capsule, delayed release pellets/oral

Major Metabolites:
4-hydroxy duloxetine glucuronide;
6-hydroxy-5-methoxy duloxetine glucoronide;
4, 6-dihydroxy duloxetine glucoronide;
5-hydroxy, 6-methoxy duloxetine sulfate

Database Search Links:
[PubMed]

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PubChem]
[PDSP Ki database]

Initial Approval:
08/03/2004


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C18H20ClNOS

Molecular Mass:
333.876 g/mol

Indications:
Major depressive disorder; diabetic peripheral neuropathic pain
Possible Mechanisms of Action:
Duloxetine inhibits the reuptake of serotonin and norepinephrine (59).

Chemical Class:
thiophenepropanamine

PubChem 2D Structure:

Generic Name:
escitalopram oxalate

Trade Name:
Lexapro ® [
Forest Labs]

IUPAC Name:
1-(3-dimethylaminopropyl)-1-
(4- fluorophenyl)-1,3-
dihydroisobenzofuran-5-
carbonitrile; ethanedioic acid

Dosage Forms/Routes:
Tablet/oral;
Capsule/oral;
Solution/oral

Major Metabolites:
S-demethylcitalopram;
S-didemethylcitalopram

Database Search Links:
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Randomized Controlled Trials
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PubChem]
[PDSP Ki database]

Initial Approval:
08/14/2002 


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C22H23FN2O5

Molecular Mass:
414.427 g/mol

Indications:
Major depressive disorder
Possible Mechanism of Action:
Escitalopram is a selective serotonin reuptake inhibitor (SSRI) (45, 60).

Chemical Class:
S-enantiomer of the racemic bicyclic phthalane derivative citalopram

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
estazolam

Trade Name:
Prosom ® [
Abbott Labs]

Common Chemical Name:
8-chloro-6-phenyl-4H-s-
triazolo[4,3-a]
[1,4]benzodiazepine

Dosage Forms/Routes:
Tablet/oral

Major Metabolites:
1-oxo-estazolam;
4-hydroxy-estazolam

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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[
PubChem]
[PDSP Ki database]

Initial Approval:
12/26/1990


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C16H11ClN4

Molecular Mass:
294.738 g/mol

Indications:
Short-term treatment of insomnia
Possible Mechanism of Action:
Estazolam is a nonselective benzodiazepine agonist (61).

Chemical Class:
triazolobenzodiazepine derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
eszopiclone

Trade Name:
Lunesta ® [
Sepracor]

IUPAC Name:

(7-oxo-2,5,8-triazabicyclo
[4.3.0]nona-1,3,5-
trien-9-yl) 2-(5-chloropyridin-
2-yl)-4-methyl-piperazine-1-
carboxylate

Dosage Forms/Routes:
Tablet/oral

Major Metabolites:
(S)-zopiclone-N-oxide;
(S)-N-desmethyl zopiclone

Database Search Links:
[PubMed]

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Randomized Controlled Trials
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PubChem]
[PDSP Ki database]

Initial Approval:
12/15/2004 


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C17H17ClN6O3

Molecular Mass:
388.808 g/mol

Indications:
Treatment of insomnia
Possible Mechanisms of Action:
Eszopiclone is the S-isomer and biologically active component of zopiclone. Zopiclone potentiates GABA-induced chloride currents in GABA-A receptors that contain the alpha-1 subunit or the combination of the beta2 subunit and the gamma2 subunit (62).
Chemical Class:
pyrrolopyrazine derivative of the cyclopyrrolone class (S-isomer of zopiclone)

PubChem 2D Structure:

Generic Name:
fluoxetine hydrochloride

Trade Name:
Prozac ® [
Eli Lilly]

IUPAC Name:
N-methyl-3-phenyl-3-[4-
(trifluoromethyl)phenoxy]-
propan-1-amine hydrochloride

Dosage Forms/Routes:
Tablet/oral;
Capsule/oral;
Solution/oral;
Capsule, delayed release pellets/oral (weekly)

Major Metabolite:
norfluoxetine

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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PubChem]
[PDSP Ki database]

Initial Approval:
12/29/1987


Manufacturers:

[FDA Search]

Product Insert:
[Prozac Capsule, Prozac Solution, and Prozac Weekly Capsule]
[Fluoxetine Tablet]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C17H19ClF3NO

Molecular Mass:
345.787 g/mol

Indications:
Major depressive disorder in adults, children, and adolescents; OCD in adults, children, and adolescents; bulimia nervosa; panic disorder
Possible Mechanisms of Action:
Fluoxetine inhibits the reuptake of serotonin (45). It is also an antagonist at serotonin 5-HT2C receptors (7, 63).

Chemical Class:
bicyclic derivative of phenylpropylamine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
fluphenazine dihydrochloride

IUPAC Name:
2-[4-[3-[2-
(trifluoromethyl)phenothiazin-
10-yl]propyl]piperazin-1-
yl]ethanol dihydrochloride

Dosage Forms/Routes:
Tablet/oral;
Injectable/injection;
Concentrate/oral;
Elixir/oral

Major Metabolites:
7-hydroxyfluphenazine;
fluphenazine sulfoxide;
fluphenazine N4-oxide

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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[
PubChem]
[PDSP Ki database]

Initial Approval:
08/24/1960


Manufacturers:

[FDA Search]

Product Insert:
[Tablet]
[Injectable] [Concentrate]
[Elixir]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C22H28Cl2F3N3OS

Molecular Mass:
510.444 g/mol

Indications:
Management of the manifestations of psychotic disorders

Possible Mechanisms of Action:
Fluphenazine is an inverse agonist at dopamine D1 (64), D2 (27), D3 receptors (65), and D5 receptors (64, 66). Fluphenazine also binds with high affinity to dopamine D4 receptors (9). The drug is an antagonist at serotonin 5-HT2A receptors (24, 27). It has high affinities for serotonin 5-HT6 and 5-HT7 receptors (27, 29). In addition, fluphenazine is an antagonist at histamine H1 receptors (27). The drug also has high affinities for alpha-1A (27), alpha-1B (67), and alpha-2C-adrenoceptors (27).

Chemical Class:
piperazine phenothiazine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
flurazepam dihydrochloride

Trade Name:
Dalmane ® [
Valeant]

IUPAC Name:
9-chloro-2-(2-diethylaminoethyl)-
6-(2-fluorophenyl)-2,5-
diazabicyclo[5.4.0]undeca-
5,8,10,12-tetraen-3-one
dihydrochloride

Dosage Forms/Routes:
Capsule/oral

Major Metabolites:
N-1-desalkylflurazepam;
N-1-hydroxyethylflurazepam

Database Search Links:
[PubMed]

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Randomized Controlled Trials
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PubChem]
[PDSP Ki database]

Initial Approval:
04/07/1970


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C21H25Cl3FN3O

Molecular Mass:
460.799 g/mol

Indications:
Short-term treatment of insomnia
Possible Mechanism of Action:
Flurazepam is a nonselective benzodiazepine agonist (68).

Chemical Class:
2-keto benzodiazepine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
fluvoxamine maleate

Trade Name:
Luvox ® [Solvay]

IUPAC Name:

but-2-enedioic acid; 2-[5-
methoxy-1-[4-
(trifluoromethyl)phenyl]-
pentylidene]aminooxyethanamine

Dosage Forms/Routes:
Tablet/oral;
Extended release capsule/oral

Major Metabolite:
fluvoxamine acid

Database Search Links:
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PubChem]
[PDSP Ki database]

Initial Approval:
12/05/1994


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C19H25F3N2O6

Molecular Mass:
434.407 g/mol

Indications:
OCD in adults, children, and adolescents
Possible Mechanisms of Action:
Fluvoxamine is a serotonin reuptake inhibitor (69). It also acts as an agonist at sigma-1 receptors (70, 71).

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
haloperidol lactate (also available as haloperidol or haloperidol decanoate)

IUPAC Name:

[4-(4-chlorophenyl)-1-[4-(4-
fluorophenyl)-4-oxo-butyl]-4-
piperidyl] 2-hydroxypropanoate

Dosage Forms/Routes:
Tablet/oral;
Injectable/injection;
Solution/oral;
Concentrate/oral

Major Metabolites:
hydroxyhaloperidol (aka reduced haloperidol);
haloperidol pyridinium;
reduced haloperidol pyridinium;
haloperidol tetrahydropyridine

Database Search Links:
[PubMed]

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[PDSP Ki database]

Initial Approval:
04/12/1967


Manufacturers:

[FDA Search]

Product Insert:
[
Tablet]
[Injectable]
[Solution]
[Concentrate]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C21H23ClFNO2

Molecular Mass:
375.864 g/mol

Indications:
Schizophrenia; control of tics and vocal utterances of Tourette's disorder
Possible Mechanisms of Action:
Haloperidol is an inverse agonist at dopamine D1 (64), D2 (72), D3 (65, 73), and D5 receptors (64). The drug is an antagonist at dopamine D4 receptors (74). It binds with relatively low affinity to serotonin 5-HT2A receptors (27). Haloperidol is a partial agonist at alpha-1-adrenoceptors (75). It is also an antagonist at sigma-1 receptors and an agonist at sigma-2 receptors (76).

Chemical Class:
butyrophenone


PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
hydroxyzine dihydrochloride

IUPAC Name:
2-[2-[4-[(4-chlorophenyl)-
phenyl-methyl]piperazin-1-
yl]ethoxy]ethanol dihydrochloride

Dosage Forms/Routes:
Tablet/oral;
Capsule/oral;
Syrup/oral;
Injectable/injection;
Suspension/oral

Major Metabolite:
cetirizine

Database Search Links:
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[PDSP Ki database]

Initial Approval:
04/12/1956


Manufacturers:

[FDA Search]

Product Insert:
[
Tablet]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C21H29Cl3N2O2

Molecular Mass:
447.825 g/mol

Indications:
For symptomatic relief of anxiety and tension associated with psychoneurosis and as an adjunct in organic disease states in which anxiety is manifested; management of pruritus due to allergic conditions such as chronic urticaria and atopic and contact dermatoses, and in histamine-mediated pruritus; as a sedative when used as pre-medication and following general anesthesia, hydroxyzine may potentiate meperidine and barbiturates, so their use in pre-anesthetic adjunctive therapy should be modified on an individual basis

Possible Mechanisms of Action:
Hydroxyzine is a histamine H1 receptor antagonist (77). The drug also binds to sigma-1 receptors (78, 79). It may bind to serotonin 5-HT2A receptors as well (80).

Chemical Class:
piperazine derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
hydroxyzine pamoate

Trade Name:
Vistaril ® [
Pfizer]

IUPAC Name:
4-[(3-carboxy-2-hydroxy-
naphthalen-1-yl)methyl]-3-
hydroxy-naphthalene-
2-carboxylic acid; 2-[2-[4-[(4-
chlorophenyl)-phenyl-
methyl]piperazin-1-
yl]ethoxy]ethanol

Dosage Forms/Routes:
Capsule/oral

Major Metabolite:
cetirizine

Database Search Links:
[PubMed]
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Randomized Controlled Trials
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PubChem]
[PDSP Ki database]

Initial Approval:
11/15/1968


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C44H43ClN2O8

Molecular Mass:
763.274 g/mol

Indications:
For symptomatic relief of anxiety and tension associated with psychoneurosis and as an adjunct in organic disease states in which anxiety is manifested; management of pruritus due to allergic conditions such as chronic urticaria and atopic and contact dermatoses, and in histamine-mediated pruritus; as a sedative when used as pre-medication and following general anesthesia, hydroxyzine may potentiate meperidine and barbiturates, so their use in pre-anesthetic adjunctive therapy should be modified on an individual basis
Possible Mechanisms of Action:
Hydroxyzine is a histamine H1 receptor antagonist (77). The drug also binds to sigma-1 receptors (78, 79). It may bind to serotonin 5-HT2A receptors as well (80).

Chemical Class:
piperazine derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
imipramine hydrochloride

Trade Name:
Tofranil ® [
Tyco Healthcare]

Common Chemical Name:
5-[3-(dimethylamino)propyl]-
10,11-dihydro-5H-dibenz
[b,f]azepine monohydrochloride

Dosage Forms/Routes:
Tablet/oral

Major Metabolite:
desipramine (aka desmethylimipramine);
2-hydroximipramine

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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PubChem]
[PDSP Ki database]

Initial Approval:
10/02/1959


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C19H25ClN2

Molecular Mass:
316.868 g/mol

Indications:
Major depressive disorder, especially endogenous depression; childhood enuresis

Possible Mechanisms of Action:
Imipramine inhibits the reuptake of serotonin and norepinephrine (81). It is an antagonist at histamine H1 and alpha-1-adrenoceptors (82, 130). In addition, the drug is an antagonist at M2 muscarinic acetylcholine receptors (83).

Chemical Class:
tertiary dibenzazepine tricyclic

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
imipramine pamoate

Trade Name:
Tofranil-PM ® [
Tyco Healthcare]

Common Chemical Name:
5-[3-(dimethylamino)propyl]-
10,11-dihydro-5H-
dibenz[b,f]azepine 4, 4'-
methylenebis-(3-hydroxy-
2-naphthoate) (2:1)

Dosage Forms/Routes:
Capsule/oral

Major Metabolite:
desipramine (aka desmethylimipramine);
2-hydroximipramine

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
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PubChem]
[PDSP Ki database]

Initial Approval:
03/11/1973


Manufacturers:

[FDA Search]

Product Insert:
[Link]

Epocrates:
[Link]

Empirical Formula:
C61H64N4O6

Molecular Mass:
949.184 g/mol

Indications:
Major depressive disorder, especially endogenous depression
Possible Mechanisms of Action:
Imipramine inhibits the reuptake of serotonin and norepinephrine (81). Imipramine binds to both histamine H1 and alpha-1-adrenoceptors (82). In addition, the drug is an antagonist at M2 muscarinic acetylcholine receptors (83).

Chemical Class:
tertiary dibenzazepine tricyclic

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
isocarboxazid

Trade Name:
Marplan ® [
Oxford]

IUPAC Name:
N-benzylamino-5-methyl-
oxazole-3-carboxamide

Dosage Forms/Routes:
Tablet/oral

Major Metabolite:
benzylhydrazine

Database Search Links:
[PubMed]

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PubChem]
[PDSP Ki database]

Initial Approval:
07/01/1959


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C12H13N3O2

Molecular Mass:
231.251 g/mol

Indications:
Major depressive disorder

Possible Mechanisms of Action:
Isocarboxazid is an irreversible inhibitor of monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) (84).

Chemical Class:
hydrazine derivative


PubChem 2D Structure:


"3D" Structure (Requires Chime):
[
Link]

Generic Name:
lamotrigine

Trade Name:
Lamictal ® [
GlaxoSmithKline]

IUPAC Name:
6-(2,3-dichlorophenyl)-1,2,4-
triazine-3,5-diamine

Dosage Forms/Routes:
Tablet/oral;
Chewable Tablet/oral

Major Metabolite:
lamotrigine 2-N-glucuronide

Database Search Links:
[PubMed]

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PubChem]
[PDSP Ki database]

Initial Approval:
12/27/1994


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C9H7Cl2N5

Molecular Mass:
256.091 g/mol

Indications:
The maintenance treatment of bipolar I disorder to delay the time to occurrence of mood episodes (depression, mania, hypomania, mixed episodes) in patients treated for acute mood episodes with standard therapy; adjunctive therapy for partial seizures in adults and pediatric patients (>/= 2 years of age); adjunctive therapy for the generalized seizures of Lennox-Gastaut syndrome in adult and pediatric patients (>/= 2 years of age)

Possible Mechanisms of Action:
Lamotrigine blocks voltage-gated sodium channels in a use-dependent manner (85). The drug preferentially binds to the channel pore in inactivated but not resting sodium channels; its inhibition of sodium channels is therefore increased by neuronal depolarization (86). Lamotrigine also inhibits N-type and P/Q-type voltage-gated calcium channels (87, 88).

Chemical Class:
phenyltriazine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
lisdexamfetamine dimesylate

Trade Name:
Vyvanse ® [Shire]

IUPAC Name:
(2S)-2,6-diamino-N-[(2S)-1-phenylpropan-
2-yl]hexanamide; methanesulfonic acid

Dosage Forms/Routes:
Capsule/oral

Major Metabolites:
p-hydroxyamphetamine;
p-hydroxynorephedrine

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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[
PubChem]
[PDSP Ki database]

Initial Approval:
02/23/2007


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C17H33N3O7S2

Molecular Mass:
455.58982 g/mol

Indications:
ADHD
Possible Mechanisms of Action:
Vyvanse is a prodrug of dextroamphetamine. After oral administration, lisdexamfetamine dimesylate is rapidly absorbed from the gastrointestinal tract and converted to dextroamphetamine, which is responsible for the drug's activity.

Chemical Class:
prodrug of the dextro isomer of d,l-amphetamine sulfate

PubChem 2D Structure:

Generic Name:
lithium carbonate

Trade Name:
Eskalith ® [
GlaxoSmithKline]

IUPAC Name:
dilithium carbonate

Dosage Forms/Routes:
Tablet/oral;
Capsule/oral;
Extended release tablet/oral

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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[
PubChem]
[PDSP Ki database]

Initial Approval:
04/06/1970


Manufacturers:

[FDA Search]

Product Insert:
[Tablet/Capsule]
[Extended Release Capsule]

RxList:
[Link]

Epocrates:
[Link]


Empirical Formula:
CLi2O3

Molecular Mass:
73.8909 g/mol

Indications:
Manic episodes associated with bipolar disorder or maintenance treatment for individuals with bipolar disorder

Possible Mechanisms of Action:
Please consult PubMed; the mechanisms of action of lithium are too complex to properly explain here.

PubChem 2D Structure:

Generic Name:
lithium citrate

IUPAC Name:
trilithium 2-hydroxypropane-1,2,3-
tricarboxylate

Dosage Forms/Routes:
Syrup/oral

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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[
PubChem]
[PDSP Ki database]

Initial Approval:
04/06/1970


Manufacturers:

[FDA Search]

Product Insert:
[Link] (syrup)

RxList:
[Link]

Epocrates:
[Link]


Empirical Formula:
C6H5Li3O7

Molecular Mass:
209.9227 g/mol

Indications:
Manic episodes associated with bipolar disorder or maintenance treatment for individuals with bipolar disorder

Possible Mechanisms of Action:
Please consult PubMed; the mechanisms of action of lithium are too complex to properly explain here.

PubChem 2D Structure:

Generic Name:
lorazepam

Trade Name:
Ativan ® [
Biovail]

IUPAC Name:
9-chloro-6-(2-chlorophenyl)-4-
hydroxy-2,5-
diazabicyclo[5.4.0]undeca-
5,8,10,12-tetraen-3-one

Dosage Forms/Routes:
Tablet/oral;
Injectable/injection;
Solution/oral;
Concentrate/oral

Major Metabolite:
lorazepam glucuronide

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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[
PubChem]
[PDSP Ki database]

Initial Approval:
09/30/1977


Manufacturers:

[FDA Search]

Product Insert:
[Tablet]
[Injectable]
[Lorazepam Intensol Concentrate]

RxList:
[Link]

Epocrates:
[Link]


Empirical Formula:
C15H10Cl2N2O2

Molecular Mass:
321.158 g/mol

Indications:
Anxiety disorders or short-term relief of the symptoms of anxiety or anxiety associated with depressive symptoms

Possible Mechanism of Action:
Lorazepam is a nonselective benzodiazepine agonist (12).

Chemical Class:
3-hydroxy benzodiazepine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
loxapine succinate

Trade Name:
Loxitane ® [
Watson]

Common Chemical Name:
2-chloro-11-(4-methyl-1-
piperazinyl)dibenz[b,f][1,4]
oxazepine

Dosage Forms/Routes:
Capsule/oral

Major Metabolites:
8-hydroxyloxapine;
7-hydroxyloxapine;
8-hydroxyamoxapine

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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[
PubChem]
[PDSP Ki database]

Initial Approval:
02/25/1975


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C22H24ClN3O5

Molecular Mass:
445.896 g/mol

Indications:
Schizophrenia
Possible Mechanisms of Action:
Loxapine is an antagonist at dopamine D1 (89), D2 (90), and D3 receptors (91). The drug also binds to D4 and D5 receptors (67). It is an antagonist at serotonin 5-HT2A receptors (92) and an inverse agonist at 5-HT2C receptors (38). In addition, the drug has been found to bind to serotonin 5-HT6 receptors (27). It also binds with low affinity to 5-HT7 receptors (27). Additional binding sites of loxapine include alpha-1A-adrenoceptors, alpha-1B-adrenoceptors, and histamine H1 receptors (67).

Chemical Class:
tricyclic dibenzoxazepine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
maprotiline hydrochloride

Major Metabolites:
desmethylmaprotiline;
maprotiline N-oxide

Dosage Forms/Routes:
Tablet/oral

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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PubChem]
[PDSP Ki database]

Initial Approval:
12/01/1980


Manufacturers:

[FDA Search]

Product Insert:
[Link]

Epocrates:
[Link]

Empirical Formula:
C20H24ClN

Molecular Mass:
313.864 g/mol

Indications:
Major Depressive Disorder
Possible Mechanisms of Action:
Maprotiline is a norepinephrine reuptake inhibitor (93). It is also a potent histamine H1 receptor antagonist (94). The drug may act as an antagonist at some muscarinic acetylcholine receptor subtypes (95, 96). Maprotiline is also a weak to moderate affinity antagonist of alpha-1-adrenoceptors (130).

Chemical Class:
tetracyclic

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
meprobamate

IUPAC Name:
[2-(carbamoyloxymethyl)-2-
methyl-pentyl] aminoformate

Dosage Forms/Routes:
Tablet/oral

Major Metabolite:
2-hydroxymeprobamate;
meprobamate glucuronide;
meprobamate glucosyluronide

Database Search Links:
[PubMed]

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PubChem]
[PDSP Ki database]

Initial Approval:
04/28/1955


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C9H18N2O4

Molecular Mass:
218.25 g/mol

Indications:
Anxiety disorders or short-term relief of the symptoms of anxiety
Possible Mechanism of Action:
Meprobamate is a barbiturate-like positive modulator of GABA-A receptor complexes (97).

Chemical Class:
propanediol dicarbamate

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
methamphetamine hydrochloride

Trade Name:
Desoxyn ® [
Ovation]

IUPAC Name:
N-methyl-1-phenyl-propan-2-
amine hydrochloride

Dosage Forms/Routes:
Tablet/oral

Major Metabolite:
amphetamine

Database Search Links:
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PubChem]
[PDSP Ki database]

Initial Approval:
12/31/1943


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C10H16ClN

Molecular Mass:
185.693 g/mol

Indications:
ADHD
Possible Mechanism of Action:
Please consult PubMed; the mechanisms of action of methamphetamine are too complex to properly explain here.
Chemical Class:
amphetamine

PubChem 2D Structure:

"3D" Structure (Requires Chime):

[Link]

Generic Name:
methylphenidate transdermal system

Trade Name:
Daytrana ® [Shire]

IUPAC Name:
methyl 2-phenyl-2-(2-
piperidyl)acetate

Dosage Forms/Routes:
Extended release film; transdermal

Major Metabolite:
dl-ritalinic acid

Database Search Links:
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PubChem]
[PDSP Ki database]

Initial Approval:
4/06/2006


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Empirical Formula:
C14H19NO2

Molecular Mass:
233.306 g/mol

Indications:
ADHD
Possible Mechanisms of Action:
Methylphenidate inhibits the reuptake of dopamine and norepinephrine (3). The drug has a higher affinity (~ 10-fold) for dopamine transporters than norepinephrine transporters (3).
Chemical Class:
piperidine derivative in a multipolymeric adhesive

PubChem 2D Structure:

"3D" Structure (Requires Chime):

[Link]
 

Generic Name:
methylphenidate hydrochloride

Trade Name:
Ritalin ® [Novartis];
Concerta ® [Alza]

IUPAC Name:
methyl 2-phenyl-2-(2-
piperidyl)acetate hydrochloride

Dosage Forms/Routes:
Tablet/oral;
Chewable tablet/oral;
Extended release tablet/oral;

Extended release capsule/oral;
Solution/oral

Major Metabolite:
dl-ritalinic acid

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
12/05/1955


Manufacturers:

[FDA Search]

Product Insert:
[Tablet - Ritalin]
[Extended Release Capsule - Ritalin LA]
[Extended Release Tablet - Concerta]

RxList:
[Link]

Epocrates:
[Link]
[Link 2] (Concerta)

Empirical Formula:
C14H20ClNO2

Molecular Mass:
269.767 g/mol

Indications:
ADHD, narcolepsy
Possible Mechanisms of Action:
Methylphenidate inhibits the reuptake of dopamine and norepinephrine (3). The drug has a higher affinity (~ 10-fold) for dopamine transporters than norepinephrine transporters (3).
Chemical Class:
piperidine derivative (a 50:50 mixture of racemic threo-methylphenidate hydrochloride)

PubChem 2D Structure:

"3D" Structure (Requires Chime):

[Link]
 

Generic Name:
mirtazapine

Trade Name:
Remeron ® [Organon]

Common Chemical Name:

1,2,3,4,10,14b-hexahydro-2-
methylpyrazino [2,1-a] pyrido
[2,3-c] benzazepine

Dosage Forms/Routes:
Tablet/oral;
Tablet/orally disintegrating

Major Metabolite:
desmethylmirtazapine

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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[
PubChem]
[PDSP Ki database]

Initial Approval:
06/14/1996 


Manufacturers:

[FDA Search]

Product Insert:
[Tablet]
[Orally Disintegrating Tablet]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C17H19N3

Molecular Mass:
265.353 g/mol

Indications:
Major depressive disorder

Possible Mechanisms of Action:
Mirtazapine is an antagonist at serotonin 5-HT2A, 5-HT2C, and 5-HT3 receptors (98). Mirtazapine is also an antagonist at alpha-2-adrenoceptors and histamine H1 receptors (98).

Chemical Class:
tetracyclic piperazinoazepine


PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
mixed amphetamine salts

Trade Name:
Adderall ® [
Shire]

Drug Constituents:
dextroamphetamine saccharate; d,l-amphetamine aspartate monohydrate; dextroamphetamine sulfate; d,l-amphetamine sulfate

Dosage Forms/Routes:
Tablet/oral;
Extended release capsule/oral

Major Metabolite:
p-hydroxyamphetamine;
p-hydroxynorephedrine; norephedrine

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
01/19/1960


Manufacturers:

[FDA Search]

Product Insert:
[Tablet]
[Extended Release Capsule]

RxList:
[Link 1]
[Link 2] (XR)

Epocrates:
[Link]

Indications:
ADHD

Possible Mechanisms of Action:
At plasmalemmal catecholamine transporters, amphetamine indirectly increases the efflux of cytosolic catecholamines so that they are released into the synaptic cleft (144). The drug causes the release of norepinephrine more potently than it causes the release of dopamine; it is much less effective as a serotonin releasing agent (144) The drug also directly inhibits norepinephrine and dopamine reuptake at higher concentrations (144). Amphetamine- induced activation of protein kinase C (PKC) beta(II) is responsible for the drug's effect on dopamine efflux (145). Na+ is cotransported with amphetamine as it enters neurons via catecholamine transporters; amphetamine-induced increases in intracellular Na+ may stimulate Na+/Ca2+ antiporters, resulting in an influx of Ca2+ into the cytosol (146). The activity of a Ca2+ dependent enzyme, phospholipase C (PLC), is increased by amphetamine, and PLC may be responsible for the increase in PKC beta(II) activity associated with amphetamine (146). Intracellular dopamine is also required for amphetamine- induced increases in PKC activity (146). Amphetamine increases the activity of phospholipase A2 (PLA2), perhaps by increasing intracellular pH (146). Low PLA2 activity may increase the activation of PKC, while high PLA2 activity may decrease the activation of PKC by amphetamine (146).

Amphetamine, a weak base, increases cytosolic dopamine and norepinephrine through two mechanisms. First, amphetamine inhibits vesicular sequestration of dopamine and norepinephrine into vesicles by directly interacting with vesicular monoamine transporter-2 (VMAT-2) (147). Second, amphetamine decreases VMAT-2 activity by reducing the pH gradients that drive monoamine uptake into vesicles (148).

At higher concentrations, amphetamine may act as a competitive antagonist at NMDA receptors (149). In addition, the drug is an agonist at TA1, a trace amine receptor (150).

Chemical Class:
amphetamine

Generic Name:
molindone hydrochloride

Trade Name:
Moban ® [Endo]

IUPAC Name:
3-ethyl-2-methyl-5-(1-oxa-4-
azoniacyclohex-4-ylmethyl)-
1,5,6,7-tetrahydroindol-4-one
chloride

Dosage Forms/Routes:
Tablet/oral

Major Metabolites:
Not known

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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[
PubChem]
[PDSP Ki database]

Initial Approval:
01/18/1974


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C16H25ClN2O2

Molecular Mass:
312.835 g/mol

Indications:
Schizophrenia
Possible Mechanisms of Action:
Molindone is an antagonist at dopamine D2 and D3 receptors (10). An unidentified metabolite of molindone may irreversibly inhibit monoamine oxidase A (151, 152).

Chemical Class:
dihydroindolone

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
nefazodone hydrochloride

IUPAC Name:
2-[3-[4-(3-
chlorophenyl)piperazin-1-
yl]propyl]-5-ethyl-4-(2-
phenoxyethyl)-1,2,4-triazol-3-
one hydrochloride

Dosage Forms/Routes:
Tablet/oral

Major Metabolites:
hydroxynefazodone;
triazoledione;
m-chlorophenylpiperazine

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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[
PubChem]
[PDSP Ki database]

Initial Approval:
12/22/1994


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C25H33Cl2N5O2

Molecular Mass:
506.467 g/mol

Indications:
Major depressive disorder
Possible Mechanisms of Action:
Nefazodone is an antagonist at serotonin 5-HT2A receptors (99). It weakly inhibits serotonin and norepinephrine reuptake (99). Nefazodone is an antagonist at histamine H1 receptors and alpha-1-adrenoceptors (45). The drug also binds to 5-HT1A receptors (45, 82) and alpha-2-adrenoceptors (45).

Chemical Class:
phenylpiperazine


PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link]

Generic Name:
nortriptyline hydrochloride

Trade Name:
Pamelor ® [
Tyco Healthcare]

Common Chemical Name:
1-Propanamine, 3-(10,11-
dihydro, 5H-dibenzo [a, d]
cyclohepten-5-ylidene)-N-
methyl-,hydrochloride

Dosage Forms/Routes:
Capsule/oral;
Solution/oral

Major Metabolite:
10-hydroxynortriptyline

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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[
PubChem]
[PDSP Ki database]

Initial Approval:
11/06/1964 


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C19H22ClN

Molecular Mass:
299.837 g/mol

Indications:
Major depressive disorder, especially endogenous depression

Possible Mechanisms of Action:
Nortriptyline inhibits the reuptake of norepinephrine (100). At serotonin 5-HT2A receptors, nortriptyline is an antagonist (101). The drug is also a low potency antagonist at histamine H1 receptors (102) and some subtypes of muscarinic acetylcholine receptors (103).

Chemical Class:
dibenzocycloheptadiene
(tricyclic)

PubChem 2D Structure:

"3D" Structure (Requires Chime):

[Link]
   

Generic Name:
olanzapine

Trade Name:
Zyprexa ® [
Eli Lilly]

Common Chemical Name:
2-methyl-4-(4-methyl-1-
piperazinyl)-10H-thieno[2,3-b]
[1,5]benzodiazepine

Dosage Forms/Routes:
Tablet/oral;
Injectable/intramuscular;
Tablet/orally disintegrating

Major Metabolites:
olanzapine 10-N-glucuronide;
olanzapine 4'-N-glucuronide;
4'-N-desmethylolanzapine;
olanzapine N-oxide

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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PubChem]
[PDSP Ki database]

Initial Approval:
09/30/1996


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C17H20N4S

Molecular Mass:
312.434 g/mol

Indications:
Schizophrenia; acute monotherapy of acute mixed or manic episodes associated with bipolar I disorder; maintenance monotherapy of bipolar patients; combination with lithium or valproate for the short-term treatment of manic episodes associated with bipolar I disorder; Zyprexa intramuscular is indicated for the treatment of agitation associated with schizophrenia and bipolar I mania

Possible Mechanisms of Action:
Olanzapine is a low potency antagonist at dopamine D1 receptors (104, 105). In addition, olanzapine acts as an inverse agonist at dopamine D2 receptors (106). The drug is an antagonist at dopamine D3 (107) and D4 receptors (74). At serotonin 5-HT2A and 5-HT2B receptors, olanzapine is a potent antagonist (105). It also exhibits potent antagonist effects at histamine H1 receptors and alpha-1 adrenoceptors (105). Olanzapine is a low affinity antagonist at M1 and M5 muscarinic acetylcholine receptors (105).

Chemical Class:
thienobenzodiazepine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link]
 

Generic Name:
olanzapine and fluoxetine
hydrochloride

Trade Name:
Symbyax ®
[Eli Lilly]

Dosage Forms/Routes:
Capsule/oral

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]

Initial Approval:
12/24/2003 


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Molecular Mass:
658.23 g/mol

Indications:
Depressive episodes associated with bipolar disorder
Possible Mechanisms of Action:
Please refer to the entries for olanzapine and fluoxetine hydrochloride.
2D Structure:

Generic Name:
oxazepam

IUPAC Name:
9-chloro-4-hydroxy-6-phenyl-
2,5-diazabicyclo[5.4.0]undeca-
5,8,10,12-tetraen-3-one

Dosage Forms/Routes:
Capsule/oral

Major Metabolite:
oxazepam
glucuronide

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
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[
PubChem]
[PDSP Ki database]

Initial Approval:
06/04/1965


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C15H11ClN2O2

Molecular Mass:
286.713 g/mol

Indications:
Anxiety disorders or short-term relief of the symptoms of anxiety; anxiety associated with depression; management of anxiety, tension, agitation, and irritability in older patients; acute tremulousness, inebriation, or anxiety associated with alcohol withdrawal
Possible Mechanism of Action:
Oxazepam is a nonselective benzodiazepine agonist (108).
Chemical Class:
3-hydroxy benzodiazepine

PubChem 2D Structure:

"3D" Structure (Requires Chime):

[Link]
   

Generic Name:
paliperidone

Trade Name:
Invega ® [Janssen]

IUPAC Name:
3-[2-[4-(6-fluoro-1,2-benzoxazol-3-
yl)piperidin-1-yl]ethyl]-9-hydroxy-2-
methyl-6,7,8,9-tetrahydropyrido[2,1-
b]pyrimidin-4-one

Dosage Forms/Routes:
Extended release tablet/oral

Major Metabolites:
Paliperidone is not metabolized extensively, and none of its metabolites could be considered "major."

Database Search Links:
[PubMed]

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PubChem]
[PDSP Ki database]

Initial Approval:
12/19/2006


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C23H27FN4O3

Molecular Mass:
426.483883 g/mol

Indications:
Acute and maintenance treatment of schizophrenia

Possible Mechanisms of Action:
Paliperidone is a centrally active dopamine Type 2 (D2) antagonist and with predominant serotonin Type 2 (5HT2A) activity (see prescribing information). Paliperidone is also active as an antagonist at α1 and α2 adrenergic receptors and H1 histaminergic receptors (see prescribing information).

Chemical Class:
benzisoxazole derivative (major active metabolite of risperidone)

PubChem 2D Structure:

Generic Name:
paroxetine hydrochloride

Trade Name:
Paxil ® [
GlaxoSmithKline]

Common Chemical Name:
(-)-trans-4R-(4'-
fluorophenyl)-3S-[(3',4'-
methylenedioxyphenoxy)
methyl] piperidine
hydrochloride hemihydrate

Dosage Forms/Routes:
Tablet/oral;
Extended release tablet/oral;
Suspension/oral

Major Metabolites:
(3S,4R)-4-(4-fluorophenyl)-3-
hydroxymethyl-1-
methylpiperidine;
3S,4R)-4-(4-fluorophenyl)-3-
(hydroxymethyl)piperidine;
(3S,4R)-4-(4-fluorophenyl)-3-
(4- hydroxy-3-
methoxyphenoxymethyl)
piperidine

Database Search Links:
[PubMed]

[Search PubMed for
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PubChem]
[PDSP Ki database]

Initial Approval:
12/29/1992


Manufacturers:

[FDA Search]

Product Insert:
[Tablet & Suspension]
[Extended Release Tablet - Paxil CR]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C19H20FNO3 ·HCl·1/2H2O

Molecular Mass:
374.8 g/mol

Indications:
Major depressive disorder; OCD; panic disorder; social anxiety disorder/social phobia; generalized anxiety disorder (GAD); PTSD

Possible Mechanisms of Action:
Paroxetine is a potent serotonin reuptake inhibitor (45). It also has a moderate affinity for the norepinephrine transporter (45). Paroxetine is a low affinity antagonist at some subtypes of muscarinic acetylcholine receptors (45). In addition, paroxetine is a nitric oxide synthase inhibitor (143).

Chemical Class:
phenylpiperidine derivative

PubChem 2D Structure:


"3D" Structure (Requires Chime):
[Link]
 

Generic Name:
paroxetine mesylate

Trade Name:
Pexeva ® [
Synthon]

IUPAC Name:
methanesulfonic acid; 3-
(benzo[1,3]dioxol-5-
yloxymethyl)-4-phenyl-piperidine

Dosage Forms/Routes:
Tablet/oral

Major Metabolites:
(3S,4R)-4-(4-fluorophenyl)-3-
hydroxymethyl-1-
methylpiperidine;
3S,4R)-4-(4-fluorophenyl)-3-
(hydroxymethyl)piperidine;
(3S,4R)-4-(4-fluorophenyl)-3-
(4- hydroxy-3-
methoxyphenoxymethyl)
piperidine

Database Search Links:
[PubMed]

[Search PubMed for
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[
PubChem]
[PDSP Ki database]

Initial Approval:
07/03/2003


Manufacturers:

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Epocrates:
[Link]

Empirical Formula:
C20H25NO6S

Molecular Mass:
407.482 g/mol

Indications:
Major depressive disorder; OCD; panic disorder; social anxiety disorder/social phobia; generalized anxiety disorder (GAD); PTSD

Possible Mechanisms of Action:
Paroxetine is a potent serotonin reuptake inhibitor (45). It also has a moderate affinity for the norepinephrine transporter (45). Paroxetine is a low affinity antagonist at some subtypes of muscarinic acetylcholine receptors (45). In addition, paroxetine is a nitric oxide synthase inhibitor (143).

Chemical Class:
phenylpiperidine derivative

PubChem 2D Structure:


"3D" Structure (Requires Chime):
[Link]
 

Generic Name:
perphenazine

IUPAC Name:
2-[4-[3-(2-chlorophenothiazin-
10-yl)propyl]piperazin-1-
yl]ethanol

Dosage Forms/Routes:
Tablet/oral;
Concentrate/oral

Major Metabolites:
deshydroxyethylperphenazine;
perphenazine sulfoxide;
7-hydroxyperphenazine

Database Search Links:
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[PDSP Ki database]

Initial Approval:
02/27/1957


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Empirical Formula:
C21H26ClN3OS

Molecular Mass:
403.969 g/mol

Indications:
Schizophrenia; control of severe nausea and vomiting in adults
Possible Mechanisms of Action:
Perphenazine is a potent dopamine D2 receptor antagonist (110). It is also an antagonist at dopamine D1 (110), D3 (10), and D4 (10) receptors. At histamine H1 receptors, perphenazine is an antagonist (27). The drug also binds to serotonin 5-HT2A, 5-HT6, and 5-HT7 receptors (27). In addition, perphenazine binds to alpha-1-adrenoceptors (27) and sigma receptors (111).

Chemical Class:
piperazinyl phenothiazine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
phenelzine sulfate

Trade Name:
Nardil ® [Pfizer]

IUPAC Name:
2-hydrazinylethylbenzene;
sulfuric acid

Dosage Forms/Routes:
Tablet/oral

Major Metabolites:
phenylacetic acid;
parahydroxyphenylacetic acid

Database Search Links:
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[PDSP Ki database]

Initial Approval:
06/09/1961


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Empirical Formula:
C8H14N2O4S

Molecular Mass:
234.274 g/mol

Indications:
Depressed patients clinically characterized as "atypical," "nonendogenous," or "neurotic." These patients often have mixed anxiety and depression and phobic or hypochondriacal features. There is less conclusive evidence of its usefulness with severely depressed patients with endogenous features.

Nardil should rarely be the first antidepressant drug used. Rather, it is more suitable for use with patients who have failed to respond to the drugs more commonly used for these conditions.

 

Possible Mechanisms of Action:
Phenelzine is an irreversible inhibitor of monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) (111). The drug also inhibits GABA transaminase and alanine transaminase (111).

Chemical Class:
hydrazine derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):

[Link]
 

Generic Name:
prochlorperazine dimaleate

Trade Name:
Compazine ® [
GlaxoSmithKline]

IUPAC Name:
2-chloro-10-[3-(4-methyl-
2,3,5,6-tetrahydropyrazin-1-
yl)propyl]-10H-phenothiazine;
4-hydroxy-4-oxo-but-2-enoate

Dosage Forms/Routes:
Tablet/oral;
Suppository/rectal

Major Metabolite:
prochlorperazine sulphoxide

Database Search Links:
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Initial Approval:
10/23/1956


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[Link]

Empirical Formula:
C24H28ClN3O4S

Molecular Mass:
606.088 g/mol

Indications:
Schizophrenia; control of severe nausea and vomiting; short-term treatment of generalized non-psychotic anxiety (should not be the first drug used in therapy)

Possible Mechanisms of Action:
Prochlorperazine is an antagonist at dopamine D2 receptors (112). Prochlorperazine also binds to dopamine D3 (113) and D4 (10) receptors. In addition, the drug binds to serotonin 5-HT2A receptors (29), histamine H1 receptors (114), and alpha-1-adrenoceptors (114).

 

Chemical Class:
piperazine phenothiazine


PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
protriptyline hydrochloride

Trade Name:
Vivactil ® [
Odyssey]

Common Chemical Name:
N-methyl-5H-dibenzo[a,d]-
cycloheptene-5-propanamine
hydrochloride

Dosage Forms/Routes:
Tablet/oral

Major Metabolites:
protriptyline 10,11 expoxide;
10-hydroxyprotriptyline;
10,11-dihydroxyprotriptyline

Database Search Links:
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Initial Approval:
09/27/1967

Manufacturers:

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Empirical Formula:
C19H22ClN

Molecular Mass:
299.837 g/mol

Indications:
Treatment of symptoms of depression in patients who are under close medical supervision. Its activating properties make it particularly suitable for withdrawn and anergic patients
Possible Mechanisms of Action:
Protriptyline is a norepinephrine reuptake inhibitor (115). The drug is an antagonist at some subtypes of muscarinic acetylcholine receptors (117, 130). It is also a low affinity antagonist at histamine H1 receptors (102, 130).
Chemical Class:
dibenzocycloheptene
derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):

[Link]
   

Generic Name:
quazepam

Trade Name:
Doral ® [MedPointe]

IUPAC Name:
9-chloro-6-(2-fluorophenyl)-2-
(2,2,2-trifluoroethyl)-2,5-
diazabicyclo[5.4.0]undeca-
5,8,10,12-tetraene-3-thione

Dosage Forms/Routes:
Tablet/oral

Major Metabolites:
2-oxoquazepam;
N-desalkyl-2-oxoquazepam

Database Search Links:
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Initial Approval:
12/27/1985


Manufacturers:

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Empirical Formula:
C17H11ClF4N2S

Molecular Mass:
386.795 g/mol

Indications:
Short-term treatment of insomnia

Possible Mechanism of Action:
Quazepam binds to GABA-A receptor complexes that contain the alpha1 subunit (118).

Chemical Class:
trifluoroethyl benzodiazepine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
quetiapine fumarate

Trade Name:
Seroquel ® [
AstraZeneca]

Common Chemical Name:
2-[2-(4-dibenzo [b,f ]
[1,4]thiazepin-11-yl-1-
piperazinyl)ethoxy]-ethanol
fumarate (2:1) (salt)

Dosage Forms/Routes:
Tablet/oral;
Extended release tablet/oral

Major Metabolites:
quetiapine sulfoxide;
7-hydroxyquetiapine

Database Search Links:
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[PDSP Ki database]

Initial Approval:
09/26/1997


Manufacturers:

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Product Insert:
[
Tablet]
[Extended Release Tablet - Seroquel Xr]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C46H54N6O8S2

Molecular Mass:
883.089 g/mol

Indications:
Schizophrenia; acute manic episodes associated with bipolar I disorder, as either monotherapy or adjunct therapy to lithium or divalproex
Possible Mechanisms of Action:
Quetiapine is an antagonist at serotonin 5-HT2A receptors (119). It is also a low potency dopamine D2 receptor inverse agonist (106). Quetiapine is an antagonist at alpha-1A-adrenoceptors (25), alpha-1B-adrenoceptors (25), and alpha-2C-adrenoceptors (40). In addition, the drug is a histamine H1 receptor antagonist (27).
Chemical Class:
dibenzothiazepine derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):

[Link]
 

Generic Name:
ramelteon

Trade Name:
Rozerem ® [
Takeda]

Common Chemical Name:
(S)-N-[2-(1,6,7,8-tetrahydro-
2H-indeno-[5,4-b]furan-8-
yl)ethyl]propionamide

Dosage Forms/Routes:
Tablet/oral

Major Metabolite:
M-II

Database Search Links:
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Initial Approval:
12/29/1993


Manufacturers:

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Empirical Formula:
C16H21NO2

Molecular Mass:
259.343 g/mol

Indications:
Insomnia characterized by difficulty with sleep onset

Possible Mechanisms of Action:
Ramelteon is an agonist at melatonin M1 and M2 receptors.

PubChem 2D Structure:
 

Generic Name:
risperidone

Trade Name:
Risperdal ® [
Janssen]

IUPAC Name:
4-[2-[4-(6-fluorobenzo[d]
isoxazol-3-yl)-1-
piperidyl]ethyl]-3-methyl-2,6-
diazabicyclo[4.4.0]deca-1,3-
dien-5-one

Dosage Forms/Routes:
Tablet/oral;
Tablet/orally disintegrating;
Solution/oral

Major Metabolite:
9-hydroxyrisperidone

Database Search Links:
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Initial Approval:
12/29/1993


Manufacturers:

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Product Insert:
[Tablets & Solution]
[Intramuscular - Risperdal Consta]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C23H27FN4O2

Molecular Mass:
410.485 g/mol

Indications:
Schizophrenia; short-term treatment of acute manic or mixed episodes associated with bipolar I disorder; combination therapy with lithium or valproate for the short-term treatment of acute manic or mixed episodes associated with bipolar I disorder

Possible Mechanisms of Action:
Risperidone is a high potency antagonist at serotonin 5-HT2A receptors (120). The drug also acts as an inverse agonist at dopamine D2 receptors (106) and is an antagonist at D3 and D4 receptors (120). Risperidone is an inverse agonist at serotonin 5-HT1B (121), 5-HT1D (121), and 5-HT2C (38, 122) receptors. It acts as an antagonist at serotonin 5-HT7 (123) receptors. In addition, risperidone is an antagonist at alpha-1A-adrenoceptors (25), alpha-1B-adrenoceptors (25), alpha-2C-adrenoceptors (40), and histamine H1 receptors (27).

Chemical Class:
benzisoxazole
derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):

[Link]
   

Generic Name:
selegiline transdermal system

Trade Name:
EMSAM ® [Somerset]

IUPAC Name:
N-methyl-1-phenyl-N-prop-2-
ynyl-propan-2-amine

Dosage Forms/Routes:
Extended release film/transdermal

Major Metabolites:
N-desmethylselegiline;
L-methamphetamine;
L-amphetamine

Database Search Links:
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[PDSP Ki database]

Initial Approval:
02/27/2006


Manufacturers:

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Prescribing Information:
[Link]

RxList:
[
Link]

Empirical Formula:
C13H17N

Molecular Mass:
187.28078 g/mol

Indications:
Major depressive disorder

Possible Mechanisms of Action:
Selegiline is an irreversible inhibitor of monoamine oxidase B (MAO-B) and monoamine oxidase A (MAO-A) according to the prescribing information for the drug. Selegiline has a greater affinity for MAO-B and is therefore selective for MAO-B at lower dosages (see the prescribing information).

Chemical Class:
levorotatory acetylenic derivative of phenethylamine

PubChem 2D Structure:
selegiline
"3D" Structure (Requires Chime):
[Link]

Generic Name:
sertraline hydrochloride

Trade Name:
Zoloft ® [Pfizer]

IUPAC Name:
4-(3,4-dichlorophenyl)-N-
methyl-tetralin-1-amine
hydrochloride

Dosage Forms/Routes:
Tablet/oral;
Concentrate/oral

Major Metabolites:
desmethylsertraline

Database Search Links:
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Initial Approval:
12/30/1991


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Product Insert:
[Tablet & Concentrate]

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Empirical Formula:
C17H18Cl3N

Molecular Mass:
342.69 g/mol

Indications:
Major depressive disorder; OCD in adults, children, and adolescents;, panic disorder; PTSD; premenstrual dysphoric disorder (PMDD); social anxiety disorder

Possible Mechanisms of Action:
Sertraline inhibits the reuptake of serotonin (45). It is also a low potency dopamine reuptake inhibitor (16).

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[Link]
   

Generic Name:
temazepam

Trade Name:
Restoril ® [
Tyco Healthcare]

IUPAC Name:
9-chloro-4-hydroxy-2-methyl-
6-phenyl-2,5-
diazabicyclo[5.4.0]undeca-
5,8,10,12-tetraen-3-one

Dosage Forms/Routes:
Capsule/oral

Major Metabolite:
temazepam glucuronide

Database Search Links:
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Initial Approval:
02/27/1981


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Empirical Formula:
C16H13ClN2O2

Molecular Mass:
300.739 g/mol

Indications:
Short-term treatment of insomnia

Possible Mechanisms of Action:
Temazepam is a nonselective benzodiazepine agonist (61).

Chemical Class:
3-hydroxy benzodiazepine

PubChem 2D Structure:

"3D" Structure (Requires Chime):

[Link]
   

Generic Name:
thioridazine hydrochloride


IUPAC Name:
10-[2-(1-methyl-2-
piperidyl)ethyl]-2-
methylsulfanyl-phenothiazine hydrochloride

Dosage Forms/Routes:
Tablet/oral;
Concentrate/oral

Major Metabolites:
mesoridazine;
sulforidazine

Database Search Links:
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Initial Approval:
03/15/1962


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Empirical Formula:
C21H27ClN2S2

Molecular Mass:
407.037 g/mol

Indications:
Management of schizophrenic patients who fail to respond adequately with other antipsychotic drugs
Possible Mechanisms of Action:
Thioridazine binds to dopamine D2, D3, and D4 receptors (67). The drug is an antagonist at serotonin 5-HT2A receptors (24). Thioridazine is also an antagonist at alpha-1A-adrenoceptors and alpha-1B-adrenoceptors (25). In addition, it is an antagonist at M1, M2, M3, M4, and M5 muscarinic acetylcholine receptors (28). Finally, thioridazine is an antagonist at histamine H1 receptors (27).

Chemical Class:
piperidine phenothiazine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
thiothixene

Trade Name:
Navane ® [
Pfizer]

IUPAC Name:
N,N-dimethyl-9-[3-(4-
methylpiperazin-1-
yl)propylidene]thioxanthene-2-
sulfonamide

Dosage Forms/Routes:
Capsule/oral;
Injectable/injection;
Concentrate/oral

Major Metabolites:
N/A (E-mail Shawn if you can provide this information.)

Database Search Links:
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Initial Approval:
07/24/1967


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Empirical Formula:
C23H29N3O2S2

Molecular Mass:
443.627 g/mol

Indications:
Schizophrenia

Possible Mechanisms of Action:
Thiothixene binds to dopamine D2 receptors, histamine H1 receptors, alpha-1A-adrenoceptors, and serotonin 5-HT7 receptors (27). It also has a moderate affinity for alpha-1B-adrenoceptors (67).

Chemical Class:
thioxanthene

PubChem 2D Structure:

"3D" Structure (Requires Chime):

[Link]
   

Generic Name:
tranylcypromine sulfate

Trade Name:
Parnate ® [
GlaxoSmithKline]

IUPAC Name:
(2-phenylcyclopropyl)
ammonium sulfate

Dosage Forms/Routes:
Tablet/oral

Major Metabolites:
N-acetyltranylcypromine;
p-hydroxytranylcypromine

Database Search Links:
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Initial Approval:
02/21/1961


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Empirical Formula:
C18H24N2O4S

Molecular Mass:
364.46 g/mol

Indications:
Major depressive episode without melancholia
Possible Mechanisms of Action:
Tranylcypromine is an irreversible inhibitor of monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) (125).
Chemical Class:
cyclopropylamine

PubChem 2D Structure:


"3D" Structure (Requires Chime):
[Link]
   

Generic Name:
trazodone hydrochloride

IUPAC Name:
8-[3-[4-(3-
chlorophenyl)piperazin-1-
yl]propyl]-6,8,9-
triazabicyclo[4.3.0]nona-2,4,9-
trien-7-one hydrochloride

Dosage Forms/Routes:
Tablet/oral

Major Metabolite:
m-chlorophenylpiperazine

Database Search Links:
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Initial Approval:
12/24/1981


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Empirical Formula:
C19H23Cl2N5O

Molecular Mass:
408.324 g/mol

Indications:
Major depressive disorder

Possible Mechanisms of Action:
Trazodone and its active metabolite,
m-chlorophenylpiperazine (m-CPP), are partial agonists at serotonin 5-HT1A receptors (126). At serotonin 5-HT2A and 5-HT2B receptors, trazodone is an antagonist (127). Trazodone and m-CPP are full agonists at serotonin 5-HT2C receptors (128). However, trazodone has a much lower affinity for 5-HT2C receptors than m-CPP (127). The drug is an antagonist at alpha-1-adrenoceptors (129, 130) and a very low affinity antagonist at histamine H1 receptors (130). In addition, m-CPP causes the extracellular release of serotonin through the serotonin transporter (131).

Chemical Class:
triazolopyridine derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
triazolam

Trade Name:
Halcion ® [
Pfizer]

Common Chemical Name:
8-chloro-6-(o-chlorophenyl)-1-
methyl -4H-s-triazolo-(4,3-
alpha)(1,4) benzodiazepine

Dosage Forms/Routes:
Tablet/oral

Major Metabolites:
alpha-hydroxytriazolam;
4-hydroxytriazolam

Database Search Links:
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Initial Approval:
11/15/1982


Manufacturers:

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Empirical Formula:
C17H12Cl2N4

Molecular Mass:
343.21 g/mol

Indications:
Short-term treatment of insomnia

Possible Mechanism of Action:
Triazolam is a nonselective benzodiazepine agonist (132).

 

Chemical Class:
triazolo benzodiazepine


PubChem 2D Structure:

"3D" Structure (Requires Chime):

[Link]
   

Generic Name:
trifluoperazine dihydrochloride

Trade Name:
Stelazine ® [
GlaxoSmithKline]

IUPAC Name:
10-[3-(4-methylpiperazin-1-
yl)propyl]-2-
(trifluoromethyl)phenothiazine
dihydrochloride

Dosage Forms/Routes:
Tablet/oral;
Concentrate/oral

Major Metabolites:
N-desmethyltrifluoperazine;
7-hydroxytrifluoperazine

Database Search Links:
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Initial Approval:
04/16/1959

Manufacturers:

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Product Insert:
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RxList:
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Epocrates:
[Link]

Empirical Formula:
C21H26Cl2F3N3S

Molecular Mass:
480.418 g/mol

Indications:
Schizophrenia; short-term treatment of generalized non-psychotic anxiety (should not be used as the first drug in therapy for most patients)

Possible Mechanisms of Action:
Trifluoperazine is an inverse agonist at dopamine D2 receptors (133). The drug also binds with moderate affinity to dopamine D4 receptors (134). The drug is an antagonist at serotonin 5-HT2A receptors (135) as well as alpha-1A-adrenoceptors and alpha-1B-adrenoceptors (25). Trifluoperazine is a low affinity antagonist at histamine H1 receptors (136). In addition, the drug inhibits interactions between calmodulin and proteins (137).

Chemical Class:
piperazine phenothiazine

PubChem 2D Structure:


"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
trimipramine maleate

Trade Name:
Surmontil ® [
Odyssey]

Common Chemical Name:
5-(3-dimethylamino-2-
methylpropyl)-10,11-dihydro-
5H-dibenz (b,f) azepine acid
maleate (racemic form)

Dosage Forms/Routes:
Capsule/oral

Major Metabolites:
desmethyltrimipramine
2-hydroxytrimipramine;
2-hydroxydesmethyltrimipramine

Database Search Links:
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Initial Approval:
06/12/1979


Manufacturers:

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Product Insert:
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[Link]

Empirical Formula:
C24H30N2O4

Molecular Mass:
410.506 g/mol

Indications:
Major depressive disorder, especially endogenous depression
Possible Mechanisms of Action:
Trimipramine is an antagonist at alpha-1A-adrenoceptors and alpha-1B-adrenoceptors (130, 138) as well as histamine H1 receptors (130). The drug also displays high affinities for serotonin 5-HT2A receptors and dopamine D2 receptors (138).
Chemical Class:
dibenzazepine (tertiary tricyclic)

PubChem 2D Structure:

"3D" Structure (Requires Chime):

[Link]
   

Generic Name:
venlafaxine hydrochloride

Trade Name:
Effexor ® [
Wyeth]

IUPAC Name:
1-[2-dimethylamino-1-(4-
methoxyphenyl)-
ethyl]cyclohexan-1-ol
hydrochloride

Dosage Forms/Routes:
Tablet/oral;
Extended release capsule/oral

Major Metabolite:
O-desmethylvenlafaxine

Database Search Links:
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Initial Approval:
12/28/1993


Manufacturers:

[FDA Search]

Product Insert:
[
Tablet]
[Extended Release Capsule - Effexor XR]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C17H28ClNO2

Molecular Mass:
313.862 g/mol

Indications:
Major depressive disorder, generalized anxiety disorder (XR version only), panic disorder (XR version only), social anxiety disorder (XR version only)

Possible Mechanisms of Action:
Venlafaxine inhibits the reuptake of serotonin and norepinephrine (139, 140). It has a much greater affinity for the serotonin transporter (139).

Chemical Class:
phenethylamine bicyclic derivative

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
zaleplon

Trade Name:
Sonata ® [
King/Wyeth]

IUPAC Name:

N-[3-(9-cyano-2,6,7-
triazabicyclo[4.3.0]nona-
2,4,7,9-tetraen-5-yl)phenyl]-
N-ethyl-ethanamide

Dosage Forms/Routes:
Capsule/oral

Major Metabolite:
5-oxo-zaleplon

Database Search Links:
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[PDSP Ki database]

Initial Approval:
08/13/1999


Manufacturers:

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Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C17H15N5O

Molecular Mass:
305.334 g/mol

Indications:
Short-term treatment of insomnia

Possible Mechanism of Action:
Zaleplon binds to GABA-A receptor complexes that contain the alpha1 subunit(132).

Chemical Class:
pyrazolopyrimidine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
ziprasidone hydrochloride
monohydrate

Trade Name:
Geodon ® [Pfizer]

IUPAC Name:
6-chloro-5-[2-[4-(7-thia-8-
azabicyclo[4.3.0]nona-1,3,5,8-
tetraen-9-yl)piperazin-1-
yl]ethyl]-1,3-dihydroindol-2-
one hydrate hydrochloride

Dosage Forms/Routes:
Capsule/oral

Major Metabolites:
benzisothiazole sulphoxide; benzisothiazole sulphone; ziprasidone sulphoxide;
S-methyl-dihydroziprasidone

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Manufacturer:
Pfizer

Initial Approval:
02/05/2001


Manufacturers:

[FDA Search]

Product Insert:
[Link]

RxList:
[Link]

Epocrates:
[Link]

Empirical Formula:
C21H24Cl2N4O2S

Molecular Mass:
467.412 g/mol

 

Indications:
Schizophrenia; acute manic or mixed episodes associated with bipolar disorder, with or without psychotic features

Possible Mechanisms of Action:
Ziprasidone is an antagonist at serotonin 5-HT2A receptors and dopamine D2 receptors (141). The drug is a partial agonist at serotonin 5-HT1B receptors and an inverse agonist at 5-HT1D receptors (121). Ziprasidone is also an inverse agonist at 5-HT2C receptors (38). The drug is an agonist at 5-HT1A receptors (142) and is known to bind to 5-HT7 receptors (27). Ziprasidone may bind to dopamine D1, D3, and D4 receptors (67). Finally, ziprasidone is a low affinity antagonist at alpha-1-adrenoceptors and histamine H1 receptors (141).

Chemical Class:
benzisothiazolyl piperazine

PubChem 2D Structure:


"3D" Structure (Requires Chime):
[
Link] 

Generic Name:
zolpidem tartrate

Trade Name:
Ambien ® [Sanofi-Aventis]

IUPAC Name:
2,3-dihydroxybutanedioic acid;
N,N-dimethyl-2-[4-methyl-8-
(4-methylphenyl)-6,9-
diazabicyclo[4.3.0]nona-
2,4,7,9-tetraen-7-yl]-
ethanamide

Dosage Forms/Routes:
Tablet/oral;
Extended release tablet/oral

Major Metabolite:
"M-3"

Database Search Links:
[PubMed]

[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
12/16/1992


Manufacturers:

[FDA Search]

Product Insert:
[
Tablet]
[Extended Release Tablet - Ambien CR]

RxList:
[Link]
[Link] (CR)

Epocrates:
[Link]

Empirical Formula:
C42H48N6O8

Molecular Mass:
764.866 g/mol

Indications:
Short-term treatment of insomnia

Possible Mechanism of Action:
Zolpidem binds to GABA-A receptor complexes that contain the alpha1 subunit (132).

Chemical Class:
imidazopyridine

PubChem 2D Structure:

"3D" Structure (Requires Chime):
[
Link] 

 

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