Drug Reference for FDA Approved Psychiatric Drugs

Drug Reference for FDA Approved Psychiatric Drugs @ Neurotransmitter.net

Drugs for the following conditions are included: depression, anxiety disorders, bipolar disorder, schizophrenia, obsessive-compulsive disorder (OCD), attention-deficit hyperactivity disorder (ADHD), post-traumatic stress disorder (PTSD), panic disorder, and insomnia.
Many of the major metabolites listed are not active metabolites.
Off-label indications are not included.
The trade names of discontinued products are not mentioned.
This list only includes information about drugs which are available as tablets or capsules for oral consumption.
MDL Chime is required to view the "3D" chemical structures.
The possible mechanisms of action that I have suggested should be subjected to critical inquiry. Please consult PubMed, the PDSP K_i database, and the referenced literature to decide for yourself if my descriptions are accurate.
Some drugs described as inverse agonists may act as antagonists depending on the cell type and function considered. See Drug-Receptor Interactions by Rob Leurs for an introduction to concepts such as inverse agonism, partial agonism, and antagonism.
See Neurotransmitter.net's list of future treatments for depression, anxiety, sleep disorders, psychosis, and ADHD for information about psychiatric drugs in the FDA's clinical trials process.
Drug references for FDA approved general anesthetic drugs, FDA approved opioid painkillers, FDA approved epilepsy drugs, FDA approved Alzheimer's disease drugs, FDA Approved Parkinson's disease drugs, FDA approved migraine drugs, and FDA approved muscle relaxants and related drugs are also available.
E-mail Shawn Thomas if you have any suggestions about how this resource could be improved.
This page has been sponsored by Epocrates, Inc.
Updated 4/04/08

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 K_i 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 K_i 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 K_i 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 K_i 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 K_i 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 K_i 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 K_i 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 K_i 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 K_i 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 K_i 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]