Drug Reference for FDA Approved Opioid Drugs @ Neurotransmitter.net


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Generic Name:
alfentanil hydrochloride

Trade Name:
Alfenta ® [Akorn]

IUPAC Name:
N-[1-[2-(4-ethyl-5-oxo-tetrazol-1-
yl)ethyl]-4-(methoxymethyl)-4-
piperidyl]-N-phenyl-propanamide
hydrochloride


Dosage Forms/Routes:
injectable/injection

Major Metabolites:
noralfentanil;
N-phenylpropionamide

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
12/29/1986


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link]

RxList:
[
Link]

Empirical Formula:
C21H33ClN6O3

Molecular Mass:
452.978 g/mol

Possible Mechanism of Action:
Alfentanil is a mu opioid receptor agonist (1).

Indications:
Alfentanil is indicated:
--as an analgesic adjunct given in incremental doses in the maintenance of anesthesia with barbiturate/ nitrous oxide/ oxygen;

--as an analgesic administered by continuous infusion with nitrous oxide/ oxygen in the maintenance of general anesthesia;

--as a primary anesthetic agent for the induction of anesthesia in patients undergoing general surgery in which endotracheal intubation and mechanical ventilation are required;

--as the analgesic component for monitored anesthesia care (MAC).

Chemical Class:
piperanilide

PubChem 2D Structure:

Generic Name:
buprenorphine hydrochloride


Trade Name:
Subutex ® [Reckitt Benckiser]

IUPAC Name:
(2S)-2-[(-)-(5R,6R,7R,14S)-
9α-cyclopropylmethyl-4,5-epoxy-
6,14-ethanomorphinan-7-yl]-3-hydroxy-
6-methoxy-3,3-dimethylbutan-2-ol


Dosage Forms/Routes:
tablet/sublingual;
injectable/injection

Major Metabolites:
norbuprenorphine

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
10/08/2002


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link]

RxList:
[
Link]

Empirical Formula:
C29H42ClNO4

Molecular Mass:
504.101 g/mol

Possible Mechanisms of Action:
Buprenorphine is a partial agonist at mu opioid receptors and nociceptin/orphanin FQ (ORL1) receptors (2). The drug has a higher affinity for the former receptors (2). Buprenorphine exhibits antagonist activity at kappa opioid receptors and delta opioid receptors, with less potent effects at the latter (3). The drug may also act as an antagonist at epsilon opioid receptors (4). Buprenorphine's active metabolite norbuprenorphine is a partial agonist at mu and kappa receptors and a full agonist at delta and ORL1 receptors (2).

Indications:
Buprenorphine is indicated for the treatment of opioid dependence.

Chemical Class:
oripavine derivative

PubChem 2D Structure:

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


Generic Name:
butorphanol tartrate

Trade Name:
Stadol ® [Apothecon]

IUPAC Name:
17-cyclobutylmethyl-
morphinan-3,14-diol

Dosage Forms/Routes:
injectable/injection
spray, metered/nasal

Major Metabolites:
norbutorphanol;
hydroxybutorphanol

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
08/22/1978


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link]

RxList:
[
Link]

Empirical Formula:
C25H35NO8

Molecular Mass:
477.547 g/mol

Possible Mechanisms of Action:
Butorphanol's primary effect involves partial agonism at mu opioid receptors (5). In addition, butorphanol is a full agonist at delta opioid receptors (6).
At kappa opioid receptors, the drug is likely to act as a full agonist (7).

Indications:
Injectable butorphanol tartrate and butorphanol tartrate nasal spray are indicated for the management of pain when the use of an opioid analgesic is appropriate.

Injectable butorphanol is also indicated as a preoperative or preanesthetic medication, as a supplement to balanced anesthesia, and for the relief of pain during labor.

Chemical Class:
morphinan derivative

PubChem 2D Structure:

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


Generic Name:
codeine phosphate

IUPAC Name:

7,8-didehydro-4,5-epoxy-3-methoxy-
17-methylmorphinan-6-ol


Dosage Forms/Routes:
[This drug is often combined with other medications.]
tablet/oral;
capsule/oral;
syrup/oral;
solution/oral


Major Metabolites:
codeine-6-glucuronide;
morphine;
normorphine;
norcodeine;
morphine-3-glucuronide;
morphine-6-glucuronide

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Manufacturers:
[FDA Search]

Prescribing
Information:

[
Link] (Tylenol® with codeine)

RxList:
[
Link]

Empirical Formula:
C36H50N2O15P2

Molecular Mass:
812.734 g/mol

Possible Mechanisms of Action:
Codeine must be metabolized in order for its analgesic activity to be exhibited (8,9). Codeine analgesia is primarily due to its metabolism to codeine-6-glucuronide (8). To a much lesser degree, the metabolism of codeine to morphine may contribute to codeine- induced analgesia (9). Codeine-6-glucuronide binds with high affinity to mu opioid receptors (10). Codeine-6-glucuronide also binds to delta opioid receptors and is less selective for mu opioid receptors than its parent compound (10).

Indications:
Codeine is indicated for the relief of mild to moderate pain. Some formulations of the drug are also indicated as cough suppressants.

Chemical Class:
phenanthrene (opium alkaloid)

PubChem 2D Structure:

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


Generic Name:
dihydrocodeine bitartrate

IUPAC Name:
4,5-alpha-epoxy-3-methoxy-17-
morphinan-6-ol


Dosage Forms/Routes:
tablet/oral;
capsule/oral

Major Metabolites:
dihydromorphine;
dihydromorphine-6-glucuronide;
nordihydrocodeine;
dihydrocodeine-6-glucuronide;
dihydromorphine-3-glucuronide

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

Initial Approval:
07/07/1958

Manufacturers:
[FDA Search]

Prescribing
Information:

[
Link] (Synalgos® DC)

Empirical Formula:
C22H29NO9

Molecular Mass:
451.467 g/mol

Possible Mechanism of Action:
Dihydrocodeine is an agonist at mu opioid receptors (11).

Indications:
Dihydrocodeine bitartrate is indicated for the relief of moderate to moderately severe pain.

Chemical Class:
semisynthetic phenanthrene derivative

PubChem 2D Structure:

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


Generic Name:
fentanyl

Trade Name:
Duragesic ® [Alza/Janssen]


IUPAC Name:
NN-(1-phenethyl-4-piperidyl)-N-
phenyl-propanamide


Dosage Forms/Routes:
film (extended release); transdermal

Major Metabolites:
norfentanyl

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
08/07/1990


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link]

RxList:
[
Link]

Empirical Formula:
C22H28N2O

Molecular Mass:
336.471 g/mol

Possible Mechanism of Action:
Fentanyl is an agonist at mu opioid receptors (12).

Indications:
DURAGESIC® is indicated for management of persistent, moderate to
severe chronic pain that:

requires continuous, around-the-clock opioid administration for an extended period of time, and

cannot be managed by other means such as non-steroidal analgesics, opioid combination products, or immediate-release opioids

DURAGESIC® should ONLY be used in patients who are already receiving opioid therapy, who have demonstrated opioid tolerance, and who require a total daily dose at least equivalent to DURAGESIC® 25 mcg/h. Patients who are considered opioid-tolerant are those who have been taking, for a week or longer, at least 60 mg of morphine daily, or at least 30 mg of oral oxycodone daily, or at least 8 mg of oral hydromorphone daily or an equianalgesic dose of another opioid.

Chemical Class:
piperanilide

PubChem 2D Structure:

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

Generic Name:
fentanyl
citrate

Trade Name:
Sublimaze ® [Akorn]


IUPAC Name:
2-hydroxypropane-1,2,3-tricarboxylic
acid; N-(1-phenethyl-4-piperidyl)-N-
phenyl-propanamide


Dosage Forms/Routes:
injectable/injection;
film (extended release)/transdermal
tablet/buccal;
lozenge/transmucosal

Major Metabolites:
norfentanyl

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
02/19/1968


Manufacturers:

[FDA Search]

Prescribing
Information:

[Link] (Sublimaze® Injectable)

[Link] (Actiq®)

[Link] (Fentora
®)

RxList:
[
Link]

Empirical Formula:
C28H36N2O8

Molecular Mass:
528.594 g/mol

Possible Mechanism of Action:
Fentanyl is an agonist at mu opioid receptors (12).

Indications:
SUBLIMAZE (fentanyl citrate) is indicated:
— for analgesic action of short duration during the anesthetic periods, premedication, induction and maintenance, and in the immediate
postoperative period (recovery room) as the need arises.
— for use as a narcotic analgesic supplement in general or regional anesthesia.
— for administration with a neuroleptic as an anesthetic premedication, for the induction of anesthesia and as an adjunct in the
maintenance of general and regional anesthesia.
— for use as an anesthetic agent with oxygen in selected high risk patients, such as those undergoing open heart surgery or certain
complicated neurological or orthopedic procedures.

ACTIQ® is indicated only for the management of breakthrough
cancer pain in patients with malignancies who are already
receiving and who are tolerant to opioid therapy for their
underlying persistent cancer pain. Patients considered opioid
tolerant are those who are taking at least 60 mg morphine/day, at
least 25 mcg transdermal fentanyl/hour, at least 30 mg of
oxycodone daily, at least 8 mg oral hydromorphone daily or an
equianalgesic dose of another opioid for a week or longer.

Chemical Class:
piperanilide

PubChem 2D Structure:

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

Generic Name:
fentanyl
hydrochloride

Trade Name:
Ionsys ® [Alza/Ortho-McNeil]


IUPAC Name:
N-(1-phenethyl-4-piperidyl)-N-
phenyl-propanamide hydrochloride


Dosage Form:
iontophoretic transdermal system

Major Metabolites:
norfentanyl

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
05/22/2006


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link]

RxList:
[
Link]

Empirical Formula:
C22H29ClN2O

Molecular Mass:
372.931 g/mol

Possible Mechanism of Action:
Fentanyl is an agonist at mu opioid receptors (12).

Indications:
IONSYS™ is indicated for the short-term management of acute postoperative pain in adult patients requiring opioid analgesia during hospitalization. Patients should be titrated to an acceptable level of analgesia before initiating treatment with IONSYS™. IONSYS™ is not intended for home use
and is, therefore, inappropriate for use in patients once they have been discharged from the
hospital. It is not recommended for patients under the age of 18 years

Chemical Class:
piperanilide

PubChem 2D Structure:

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


Generic Name:
hydrocodone bitartrate

Trade Name:
Vicodin ® [Abbott]
(hydrocodone bitartrate combined with acetaminophen)

Common Chemical Name:
4,5α-epoxy-3-methoxy-
17-methylmorphinan-6-one tartrate (1:1) hydrate (2:5)

Dosage Forms/Routes:
tablet/oral;
capsule/oral;
solution/oral;
suspension/oral

Major Metabolites:
hydromorphone;
norhydrocodone

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
01/07/1983


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link] (generic hydrocodone bitartrate plus acetaminophen)

RxList:
[
Link]

Empirical Formula:
C18H21NO3C4H6O6
H2O

Molecular Mass:
494.490 g/mol

Possible Mechanism of Action:
Hydrocodone is a mu opioid receptor agonist. (13).

Indications:
Hydrocodone is indicated for the treatment of moderate to moderately severe pain.

Chemical Class:
phenanthrene derivative

PubChem 2D Structure:

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


Generic Name:
hydromorphone hydrochloride

Trade Name:
Dilaudid ® [Abbott]

Common Chemical Name:
4,5α-epoxy-3-hydroxy-
17-methylmorphinan-6-one hydrochloride


Dosage Forms/Routes:
tablet/oral;
solution/oral;
injectable/injection;
extended release capsule; oral


Major Metabolites:
hydromorphone-3-glucuronide;
hydromorphone-3-glucoside;
dihydroisomorphine-6-glucuronide

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
01/11/1984


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link]

RxList:
[
Link]

Empirical Formula:
C17H20ClNO3

Molecular Mass:
321.798 g/mol

Possible Mechanism of Action:
Hydromorphone is a mu opioid receptor agonist (14).

Indications:
Hydromorphone is indicated for the management of pain in patients where an opioid analgesic is appropriate.

Chemical Class:
morphinan derivative

PubChem 2D Structure:

Generic Name:
levorphanol tartrate

Trade Name:
Levo-Dromoran ® [Valeant]

Common Chemical Name:
levo-3-hydroxy-N-methylmorphinan


Dosage Forms/Routes:
tablet/oral

Major Metabolites:
levorphanol glucuronide

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
01/08/1953

Manufacturers:
[FDA Search]

RxList:
[
Link]

Empirical Formula:
C21H33NO9

Molecular Mass:
443.488 g/mol

Possible Mechanisms of Action:
Levorphanol binds with high affinity to mu, kappa, and delta opioid receptors (15). The drug has been identified as a full agonist at kappa opioid receptors (16). Furthermore, it binds with high affinity to kappa1 and kappa3 but not kappa2 receptors (17). Levorphanol may also exhibit non-competitive NMDA antagonist activity at high doses (18).

Indications:
Levorphanol is indicated for the management of moderate to severe pain or as a preoperative medication where an opioid analgesic is appropriate.

Chemical Class:
morphinan derivative

PubChem 2D Structure:

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

Generic Name:
meperidine

Trade Name:
Demerol ® [Sanofi-Aventis]

IUPAC Name:
ethyl 1-methyl-4-phenyl-piperidine-
4-carboxylate hydrochloride


Dosage Forms/Routes:
tablet/oral

Major Metabolites:
normeperidine

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
11/10/1942


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link]

RxList:
[
Link]

Empirical Formula:
C15H22ClNO2

Molecular Mass:
283.793 g/mol

Possible Mechanisms of Action:
Meperidine is a partial agonist at mu opioid receptors (22, 5). The drug also inhibits the serotonin reuptake transporter (23).

Indications:
Meperidine is indicated:
For the relief of moderate to severe pain (parenteral and oral forms)
For preoperative medication (parenteral form only)
For support of anesthesia (parenteral form only)
For obstetrical analgesia (parenteral form only)

 

Chemical Class:
phenylpiperidine

PubChem 2D Structure:

Generic Name:
methadone hydrochloride

Trade Name:
Dolophine ® [Roxane]

IUPAC Name:
6-dimethylamino-4,4-diphenyl-
heptan-3-one hydrochloride


Dosage Forms/Routes:
tablet/oral;
injectable/injection;
concentrate/oral;
solution/oral

Major Metabolites:
2-ethylidene-1,5-dimethyl-3,3-
diphenylpyrrolidine (EDDP);
2-ethyl-5-methyl-3,3-diphenyl-1-
pyrroline (EMDP)

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
08/13/1947


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link]

RxList:
[
Link]

Empirical Formula:
C21H28ClNO

Molecular Mass:
345.906 g/mol

Possible Mechanisms of Action:
Methadone is a mu opioid receptor agonist (19, 20). Based on its intermediate efficacy at activating mu opioid receptors, methadone desensitizes the receptors disproportionally more than comparable opioids (20). In addition, methadone may bind to kappa3 opioid receptors (21).

Indications:
Methadone is indicated:
For the treatment of moderate to severe pain not responsive to non-narcotic analgesics.
For detoxification treatment of opioid addiction (heroin or other morphine-like drugs).
For maintenance treatment of opioid addiction (heroin or other morphine-like drugs), in conjunction with
appropriate social and medical services.

Chemical Class:
phenylheptylamine

PubChem 2D Structure:

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

Generic Name:
morphine sulfate

Trade Name:
MS Contin ® [Purdue Pharma]

Common Chemical Name:
7,8-didehydro-4,5α-epoxy-17-
methylmorphinan-
3,6α-diol sulfate (2:1) (salt)
pentahydrate

Dosage Forms/Routes:
tablet/oral;
extended release tablet/oral;
extended release capsule/oral
;
injectable/injection;
injectable, liposomal; injection

Major Metabolites:
morphine-6-glucuronide (M6G);
morphine-3-glucuronide (M3G)

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link] (MS Contin®)

RxList:
[
Link] (MS Contin®)

[Link] (Roxanol®)

[Link] (Duramorph®)

DrugBank:
[Link]

Empirical Formula:
(C17H19NO3)2·H2SO4·5H2O

Molecular Mass:
758.83 g/mol

Possible Mechanisms of Action:
Morphine and its key active metabolite, morphine-6-glucuronide (M6G), activate mu opioid receptors. Morphine and M6G are partial agonists at some splice variants of the mu opioid receptor and full agonists at other splice variants of the receptor (24). To a much lesser degree, morphine and M6G may act as agonists at kappa and delta opioid receptors (25). Morphine has a higher affinity for kappa opioid receptors than M6G, but morphine has less affinity than M6G for delta opioid receptors (25). Morphine is a partial agonist at delta receptors (6).

Indications:
Immediate release morphine tablets are indicated for the relief of severe acute and severe chronic pain.

Sustained release morphine tablets and capsules are indicated for the relief of pain in patients who require opioid analgesics for more than a few days.

Duramorph
® is a systemic narcotic analgesic for administration by the intravenous, epidural or intrathecal routes. It is used for the management of pain not responsive to non-narcotic analgesics. Duramorph® administered epidurally or intrathecally, provides pain relief for extended periods without attendant loss of motor, sensory or sympathetic function.

Chemical Class:
phenanthrene (opium alkaloid)

PubChem 2D Structure:

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


Generic Name:
nalbuphine hydrochloride

Trade Name:
Nubain ® [Endo]

Common Chemical Name:
17-(cyclobutylmethyl)-4,5a-
epoxymorphinan-3,6a,14-triol
hydrochloride


Dosage Forms/Routes:
injectable/injection

Major Metabolites:
noroxymorphine

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
05/15/1979


Manufacturers:

[FDA Search]

RxList:
[
Link]

Empirical Formula:
C21H28ClNO4

Molecular Mass:
393.904 g/mol

Possible Mechanisms of Action:
Nalbuphine is a partial agonist at mu opioid receptors (22, 5). The drug is also a partial agonist at kappa opioid receptors (7).

Indications:
Nalbuphine is indicated for the relief of moderate to severe pain. Nalbuphine can also be used as a supplement to balanced anesthesia, for preoperative and postoperative analgesia, and for obstetrical analgesia during labor and delivery.

Chemical Class:
morphinan derivative

PubChem 2D Structure:

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

Generic Name:
oxycodone
hydrochloride

Trade Name:
Oxycontin ® [Purdue Pharma]

IUPAC Name:
4, 5-epoxy-14-hydroxy-3- methoxy-
17-methylmorphinan-6-one
hydrochloride

Dosage Forms/Routes:
tablet/oral;
extended release tablet/oral;
capsule/oral;
solution/oral

Major Metabolites:
oxymorphone;
noroxymorphone;
noroxycodone

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
4/12/1950


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link] (Oxycontin)

[Link] (Percocet)

[Link] (Percodan)

RxList:
[
Link]

Empirical Formula:
C18H22ClNO4

Molecular Mass:
351.824 g/mol

Possible Mechanism of Action:
Oxycodone is a mu opioid receptor agonist (26). Kappa opioid receptor agonism and oxycodone's metabolites probably do not contribute to the drug's mechanism of action (26).

Indications:
In immediate-release formulations, oxycodone hydrochloride is indicated for the treatment of moderate to moderately severe pain.

OxyContin Tablets are a controlled-release oral formulation of oxycodone hydrochloride indicated for the management of moderate to severe pain when a continuous, around-the-clock analgesic is needed for an extended period of time.

OxyContin is NOT intended for use as a prn analgesic.

Physicians should individualize treatment in every case, initiating therapy at the appropriate point along a progression from non-opioid analgesics, such as non-steroidal antiinflammatory drugs and acetaminophen to opioids in a plan of pain management such as outlined by the World Health Organization, the Agency for Healthcare Research and Quality
(formerly known as the Agency for HealthCare Policy and Research), the Federation of State
Medical Boards Model Guidelines, or the American Pain Society.


OxyContin is not indicated for pain in the immediate postoperative period (the first 12-24 hours following surgery), or if the pain is mild, or not expected to persist for an extended period of time. OxyContin is only indicated for postoperative use if the patient is already receiving the drug prior to surgery or if the postoperative pain is expected to be moderate to severe and persist for an extended period of time. Physicians should individualize treatment, moving from parenteral to oral analgesics as appropriate. (See American Pain Society guidelines.)

Chemical Class:
semisynthetic phenanthrene derivative

PubChem 2D Structure:

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


Generic Name:
oxymorphone hydrochloride

Trade Name:
Opana ® [Endo]

Common Chemical Name:
4, 5a-epoxy-3, 14-dihydroxy-17-
methylmorphinan-6-one hydrochloride


Dosage Forms/Routes:
tablet/oral;
extended release tablet/oral;
injectable/injection

Major Metabolites:
oxymorphone-3-glucuronide;
6-OH-oxymorphone

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
04/02/1959


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link] (Opana immediate release)

[Link] (Opana ER)

RxList:
[
Link]

Empirical Formula:
C17H20ClNO4

Molecular Mass:
337.798 g/mol

Possible Mechanism of Action:
Oxymorphone is a mu opioid receptor agonist (26)

Indications:
Opana immediate release is indicated for the relief of moderate to severe acute pain where the use of an opioid is appropriate.

Opana ER is indicated for the relief of moderate to severe pain in patients requiring continuous, around-the-clock opioid treatment for an extended period of time.

Opana ER is not intended for use as a prn analgesic.

Opana
ER is not indicated for pain in the immediate post-operative period (12-24 hours following surgery) for patients not previously taking opioids because of the risk of oversedation and respiratory depression requiring reversal with opioid antagonists. Opana ER is not indicated for pain in the post-operative period if the pain is mild or not expected to persist for an extended period of time.

Chemical Class:
semisynthetic phenanthrene derivative

PubChem 2D Structure:

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

Generic Name:
pentazocine hydrochloride

Trade Name:
Talacen ® [Endo]

Common Chemical Name:
1,2,3,4,5,6-hexahydro-6,11-dimethyl-
3-(3-methyl-2-butenyl)-2,6-methano-
3-benzazocin-8-ol
hydrochloride

Dosage Forms/Routes:
tablet/oral

Major Metabolites:
pentazocine glucuronide

Database Search Links:
[PubMed]
[Search PubMed for
Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
02/03/1969


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link]

RxList:
[
Link]

Empirical Formula:
C19H28ClNO

Molecular Mass:
321.884 g/mol

Possible Mechanisms of Action:
Pentazocine is likely to be a partial agonist at mu opioid receptors (27). The drug is also a partial agonist at kappa opioid receptors (16).

Indications:
Pentazocine hydrochloride is indicated for the treatment of mild to moderate pain.

Chemical Class:
benzomorphan derivative

PubChem 2D Structure:

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


Generic Name:
pentazocine lactate

Trade Name:
Talwin ® [Hospira]

Common Chemical Name:
1,2,3,4,5,6-hexahydro-6,11-dimethyl-
3-(3-methyl-2-butenyl)-2,6-methano-
3-benzazocin-8-ol
lactate

Dosage Forms/Routes:
injectable/injection

Major Metabolites:
pentazocine glucuronide

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

Initial Approval:
07/24/1967


Manufacturers:

[FDA Search]

Empirical Formula:
C22H33NO4

Molecular Mass:
375.502 g/mol

Possible Mechanisms of Action:
Pentazocine is likely to be a partial agonist at mu opioid receptors (27). The drug is also a partial agonist at kappa opioid receptors (16).

Indications:
Pentazocine lactate is indicated for the treatment of moderate to severe pain. The drug is also indicated as a preoperative or preanesthetic medication and as a supplement to surgical anesthesia.

Chemical Class:
benzomorphan derivative

PubChem 2D Structure:

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


Generic Name:
propoxyphene hydrochloride

Trade Name:
Darvon ® [Xanodyne]

IUPAC Name:
[(2S,3R)-4-dimethylamino-3-methyl-
1,2-diphenyl-butan-2-yl] propanoate
hydrochloride


Dosage Forms/Routes:
tablet/oral;
capsule/oral

Major Metabolites:
norpropoxyphene

Database Search Links:
[PubMed]
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Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
08/16/1957


Manufacturers:

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Prescribing
Information:

[
Link]

RxList:
[
Link]

Empirical Formula:
C22H30ClNO2

Molecular Mass:
375.932 g/mol

Possible Mechanism of Action:
Propoxyphene is a weak mu opioid receptor agonist (28).
A metabolite of the drug, norpropoxyphene, may induce cardiotoxic effects that result from an alteration of sodium and potassium ion permeability in cardiac tissue (37).

Indications:
Propoxyphene hydrochloride is indicated for the treatment of mild to moderate pain.

Chemical Class:
phenylheptylamine

PubChem 2D Structure:

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


Generic Name:
propoxyphene napsylate

Trade Name:
Darvon-N ® [x]

IUPAC Name:
[(2S,3R)-4-dimethylamino-3-methyl-
1,2-diphenyl-butan-2-yl] propanoate;
naphthalene-2-sulfonic acid


Dosage Forms/Routes:
tablet/oral

Major Metabolites:
norpropoxyphene

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

Initial Approval:
09/09/1971


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link]

RxList:
[
Link]

Empirical Formula:
C32H37NO5S

Molecular Mass:
547.706 g/mol

Possible Mechanism of Action:
Propoxyphene is a weak mu opioid receptor agonist (28).
A metabolite of the drug, norpropoxyphene, may induce cardiotoxic effects that result from an alteration of sodium and potassium ion permeability in cardiac tissue (37).

Indications:
Propoxyphene napsylate is indicated for the treatment of mild to moderate pain.

Chemical Class:
phenylheptylamine

PubChem 2D Structure:

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


Generic Name:
remifentanil hydrochloride

Trade Name:
Ultiva ® [Abbott]

IUPAC Name:
methyl 1-(2-methoxycarbonylethyl)-
4-(phenyl-propanoyl-amino)piperidine-
4-carboxylate hydrochloride


Dosage Forms/Routes:
injectable/injection

Major Metabolites:
remifentanil acid

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

Initial Approval:
07/12/1996


Manufacturers:

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Prescribing
Information:

[
Link]

RxList:
[
Link]

Empirical Formula:
C20H29ClN2O5

Molecular Mass:
412.907 g/mol

Possible Mechanisms of Action:
Remifentanil is an agonist at mu opioid receptors (29, 30).

Indications:
Remifentanil is indicated for IV administration:
1. As an analgesic agent for use during the induction and maintenance of general anesthesia for inpatient and outpatient procedures.
2. For continuation as an analgesic into the immediate postoperative period in adult patients under the direct supervision of an anesthesia practitioner in a postoperative anesthesia care unit or intensive care setting.
3. As an analgesic component of monitored anesthesia care in adult patients.

Chemical Class:
piperanilide

PubChem 2D Structure:

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


Generic Name:
sufentanil citrate

Trade Name:
Sufenta ® [Akorn]

IUPAC Name:
2-hydroxypropane-1,2,3-tricarboxylic
acid; N-[4-(methoxymethyl)-1-(2-
thiophen-2-ylethyl)-4-piperidyl]-N-
phenyl-propanamide


Dosage Forms/Routes:
injectable/injection

Major Metabolites:
norsufentanil

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

Initial Approval:
05/04/1984


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link]

Empirical Formula:
C28H38N2O9S

Molecular Mass:
578.675 g/mol

Possible Mechanisms of Action:
Sufentanil is a mu opioid receptor agonist (31).

Indications:
Sufenta (sufentanil citrate) is indicated for intravenous administration in adults and pediatric patients:
as an analgesic adjunct in the maintenance of balanced general anesthesia in patients who are intubated and ventilated.
as a primary anesthetic agent for the induction and maintenance of anesthesia with 100% oxygen in patients undergoing major surgical procedures, in patients who are intubated and ventilated, such as cardiovascular surgery or neurosurgical procedures in the sitting position, to provide favorable myocardial
and cerebral oxygen balance or when extended postoperative ventilation is anticipated.

Sufentanil citrate is indicated for epidural administration as an analgesic combined with low dose bupivacaine, usually 12.5 mg per administration,
during labor and vaginal delivery.

Chemical Class:
piperanilide

PubChem 2D Structure:

Generic Name:
tramadol hydrochloride

Trade Name:
Ultram ® [Ortho-McNeil]

IUPAC Name:
(1R,2R)-2-(dimethylaminomethyl)-1-
(3-methoxyphenyl)cyclohexan-1-ol
hydrochloride


Dosage Forms/Routes:
tablet/oral;
extended release tablet/oral;
orally disintegrating tablet/oral;

Major Metabolites:
O-desmethyltramadol;
N-desmethyltramadol

Database Search Links:
[PubMed]
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Randomized Controlled Trials
]

[
PubChem]
[PDSP Ki database]

Initial Approval:
03/03/1995


Manufacturers:

[FDA Search]

Prescribing
Information:

[
Link] (Ultram)

[Link] (Ultram ER)

RxList:
[
Link]

Empirical Formula:
C16H26ClNO2

Molecular Mass:
299.836 g/mol

Possible Mechanisms of Action:
Tramadol is a weak agonist at mu opioid receptors (32). A metabolite of tramadol, O-desmethyltramadol, is a more potent mu opioid agonist than its parent drug (33). In addition, tramadol inhibits the reuptake of norepinephrine and serotonin (32). Tramadol may also induce the efflux of serotonin from the serotonin transporter (34) and norepinephrine from the norepinephrine transporter (35). Finally, the metabolite O-desmethyltramadol may act as an antagonist at serotonin 5-HT2C receptors (36).

Indications:
Ultram (tramadol hydrochloride) is indicated for the management of moderate to moderately severe pain in adults.

Ultram ER is indicated for the management of moderate to moderately severe chronic pain in adults who require around-the-clock treatment of their pain for an extended period of time.

Chemical Class:
cyclohexanol derivative

PubChem 2D Structure:

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


References:

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Comparative binding of mu and delta selective ligands in whole brain and pons/medulla homogenates from rat: affinity profiles of fentanyl derivatives.
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2. Rothman RB, Gorelick DA, Heishman SJ, Eichmiller PR, Hill BH, Norbeck J, Liberto JG.
Comparison of pharmacological activities of buprenorphine and norbuprenorphine: norbuprenorphine is a potent opioid agonist.
J Pharmacol Exp Ther 2001 May;297(2):688-95 [Abstract]

3. Negus SS, Bidlack JM, Mello NK, Furness MS, Rice KC, Brandt MR.
Delta opioid antagonist effects of buprenorphine in rhesus monkeys.
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Buprenorphine blocks epsilon- and micro-opioid receptor-mediated antinociception in the mouse.
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5
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Relationship between rate and extent of G protein activation: comparison between full and partial opioid agonists.
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6. Gharagozlou P, Demirci H, Clark JD, Lameh J.
Activation profiles of opioid ligands in HEK cells expressing delta opioid receptors.
BMC Neurosci. 2002 Nov 18;3:19. Epub 2002 Nov 18. [Full Text]

7. Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J.
Pharmacological profiles of opioid ligands at kappa opioid receptors.
BMC Pharmacol. 2006 Jan 25;6:3. [Full Text]

8. Vree TB, van Dongen RT, Koopman-Kimenai PM.
Codeine analgesia is due to codeine-6-glucuronide, not morphine.
Int J Clin Pract. 2000 Jul-Aug;54(6):395-8. [Abstract]

9. Lotsch J, Skarke C, Schmidt H, Rohrbacher M, Hofmann U, Schwab M, Geisslinger G.
Evidence for morphine-independent central nervous opioid effects after administration of codeine: contribution of other codeine metabolites.
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10. Mignat C, Wille U, Ziegler A.
Affinity profiles of morphine, codeine, dihydrocodeine and their glucuronides at opioid receptor subtypes.
Life Sci. 1995;56(10):793-9. [Abstract]

11. Thompson, Chad M., Wojno, Heidi, Greiner, Elisabeth, May, Everette L., Rice, Kenner C., Selley, Dana E.
Activation of G-Proteins by Morphine and Codeine Congeners: Insights to the Relevance of O- and N-Demethylated Metabolites at {micro}- and {delta}-Opioid Receptors
J Pharmacol Exp Ther 2004 308: 547-554 [Full Text]

12. Maguire P, Tsai N, Kamal J, Cometta-Morini C, Upton C, Loew G.
Pharmacological profiles of fentanyl analogs at mu, delta and kappa opiate receptors.
Eur J Pharmacol. 1992 Mar 24;213(2):219-25. [Abstract]

13. Codd EE, Shank RP, Schupsky JJ, Raffa RB.
Serotonin and norepinephrine uptake inhibiting activity of centrally acting analgesics: structural determinants and role in antinociception.
J Pharmacol Exp Ther. 1995 Sep;274(3):1263-70. [Abstract]

14. Gharagozlou P, Demirci H, David Clark J, Lameh J.
Activity of opioid ligands in cells expressing cloned mu opioid receptors.
BMC Pharmacol. 2003 Jan 4;3(1):1. Epub 2003 Jan 04. [Abstract]

15. Zhang A, Xiong W, Bidlack JM, Hilbert JE, Knapp BI, Wentland MP, Neumeyer JL.
10-Ketomorphinan and 3-substituted-3-desoxymorphinan analogues as mixed kappa and micro opioid ligands: synthesis and biological evaluation of their binding affinity at opioid receptors.
J Med Chem. 2004 Jan 1;47(1):165-74. [Abstract]

16. Wang Y, Li JG, Huang P, Xu W, Liu-Chen LY.
Differential effects of agonists on adenylyl cyclase superactivation mediated by the kappa opioid receptors: adenylyl cyclase superactivation is independent of agonist-induced phosphorylation, desensitization, internalization, and down-regulation.
J Pharmacol Exp Ther. 2003 Dec;307(3):1127-34. Epub 2003 Oct 13. [Full Text]

17. Tive L, Ginsberg K, Pick CG, Pasternak GW.
Kappa 3 receptors and levorphanol-induced analgesia.
Neuropharmacology. 1992 Sep;31(9):851-6. [Abstract]

18. Stringer M, Makin MK, Miles J, Morley JS.
d-morphine, but not l-morphine, has low micromolar affinity for the non-competitive N-methyl-D-aspartate site in rat forebrain. Possible clinical implications for the management of neuropathic pain.
Neurosci Lett. 2000 Dec 1;295(1-2):21-4. [Abstract]

19. Blake AD, Bot G, Freeman JC, Reisine T.
Differential opioid agonist regulation of the mouse mu opioid receptor.
J Biol Chem. 1997 Jan 10;272(2):782-90. [Full Text]

20. Yu Y, Zhang L, Yin X, Sun H, Uhl GR, Wang JB.
Mu opioid receptor phosphorylation, desensitization, and ligand efficacy.
J Biol Chem. 1997 Nov 14;272(46):28869-74. [Full Text]

21. Standifer KM, Cheng J, Brooks AI, Honrado CP, Su W, Visconti LM, Biedler JL, Pasternak GW.
Biochemical and pharmacological characterization of mu, delta and kappa 3 opioid receptors expressed in BE(2)-C neuroblastoma cells.
J Pharmacol Exp Ther. 1994 Sep;270(3):1246-55. [Abstract]

22. Emmerson PJ, Clark MJ, Medzihradsky F, Remmers AE.
Membrane microviscosity modulates mu-opioid receptor conformational transitions and agonist efficacy.
J Neurochem. 1999 Jul;73(1):289-300. [Full Text]

23. Lomenzo SA, Izenwasser S, Gerdes RM, Katz JL, Kopajtic T, Trudell ML.
Synthesis, dopamine and serotonin transporter binding affinities of novel analogues of meperidine.
Bioorg Med Chem Lett. 1999 Dec 6;9(23):3273-6. [Abstract]

24.Pan L, Xu J, Yu R, Xu MM, Pan YX, Pasternak GW.
Identification and characterization of six new alternatively spliced variants of the human mu opioid receptor gene, Oprm.
Neuroscience. 2005;133(1):209-20. [Abstract]

25.Kilpatrick GJ, Smith TW.
Morphine-6-glucuronide: actions and mechanisms.
Med Res Rev. 2005 Sep;25(5):521-44. [Abstract]

26. Lalovic B, Kharasch E, Hoffer C, Risler L, Liu-Chen LY, Shen DD.
Pharmacokinetics and pharmacodynamics of oral oxycodone in healthy human subjects: role of circulating active metabolites.
Clin Pharmacol Ther. 2006 May;79(5):461-79. [Abstract]

27. Jones HE, Bigelow GE, Preston KL.
Assessment of opioid partial agonist activity with a three-choice hydromorphone dose-discrimination procedure.
J Pharmacol Exp Ther. 1999 Jun;289(3):1350-61. [Full Text]

28. Yoburn BC, Shah S, Chan K, Duttaroy A, Davis T.
Supersensitivity to opioid analgesics following chronic opioid antagonist treatment: relationship to receptor selectivity.
Pharmacol Biochem Behav. 1995 Jun-Jul;51(2-3):535-9. [Abstract]

29. Poisnel G, Quentin T, Barre L, Coquerel A, Debruyne D.
Competitive displacement binding assay on rat brain sections and using a beta-imager: application to mu-opioid ligands.
J Neurosci Methods. 2006 Jun 30;154(1-2):60-7. Epub 2006 Jan 19. [Abstract]

30. Richardson SP, Egan TD.
The safety of remifentanil by bolus injection.
Expert Opin Drug Saf. 2005 Jul;4(4):643-51. [Abstract]

31. Emmerson PJ, Liu MR, Woods JH, Medzihradsky F.
Binding affinity and selectivity of opioids at mu, delta and kappa receptors in monkey brain membranes.
J Pharmacol Exp Ther. 1994 Dec;271(3):1630-7. [Abstract]

32. Raffa RB, Friderichs E, Reimann W, Shank RP, Codd EE, Vaught JL.
Opioid and nonopioid components independently contribute to the mechanism of action of tramadol, an 'atypical' opioid analgesic.
J Pharmacol Exp Ther. 1992 Jan;260(1):275-85. [Abstract]

33. Raffa RB, Friderichs E, Reimann W, Shank RP, Codd EE, Vaught JL, Jacoby HI, Selve N.
Complementary and synergistic antinociceptive interaction between the enantiomers of tramadol.
J Pharmacol Exp Ther. 1993 Oct;267(1):331-40. [Abstract]

34. Bamigbade TA, Davidson C, Langford RM, Stamford JA.
Actions of tramadol, its enantiomers and principal metabolite, O-desmethyltramadol, on serotonin (5-HT) efflux and uptake in the rat dorsal raphe nucleus.
Br J Anaesth. 1997 Sep;79(3):352-6. [Full Text]

35. Halfpenny DM, Callado LF, Hopwood SE, Bamigbade TA, Langford RM, Stamford JA.
Effects of tramadol stereoisomers on norepinephrine efflux and uptake in the rat locus coeruleus measured by real time voltammetry.
Br J Anaesth. 1999 Dec;83(6):909-15. [Full Text]

36. Horishita T, Minami K, Uezono Y, Shiraishi M, Ogata J, Okamoto T, Shigematsu A.
The tramadol metabolite, O-desmethyl tramadol, inhibits 5-hydroxytryptamine type 2C receptors expressed in Xenopus Oocytes.
Pharmacology. 2006;77(2):93-9. Epub 2006 May 5. [Abstract]

37. Ulens C, Daenens P, Tytgat J.
Norpropoxyphene-induced cardiotoxicity is associated with changes in ion-selectivity and gating of HERG currents.
Cardiovasc Res. 1999 Dec;44(3):568-78. [Abstract]