The first mixed agonist-antagonist analgesic to be marketed. It is an agonist at the kappa and sigma opioid receptors and has a weak antagonist action at the mu receptor. (From AMA Drug Evaluations Annual, 1991, p97)

Structure

Similar Structures

Synonyms

Pentazocin
Pentazocina
Pentazocine
Pentazocinum

External IDs

CS 350 / NIH 7958 / Win 20228

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Pentazocine Hydrochloride	A36BXO4PPX	64024-15-3	OQGYMIIFOSJQSF-DTOXXUQYSA-N
Pentazocine Lactate	1P2XIB510O	17146-95-1	QNLDTXPVZPRSAM-DTOXXUQYSA-N

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Talwin	Injection, solution	30 mg/1mL	Intramuscular; Intravenous; Subcutaneous	General Injectables & Vaccines	2010-08-01	2017-01-18
Talwin	Tablet	50 mg	Oral	Sanofi Aventis	1970-12-31	Not applicable
Talwin	Injection, solution	30 mg/1mL	Intramuscular; Intravenous; Subcutaneous	Physicians Total Care, Inc.	1995-12-20	2001-06-30
Talwin	Injection, solution	30 mg/1mL	Intramuscular; Intravenous; Subcutaneous	Hospira, Inc.	2006-10-06	2006-11-09
Talwin	Injection, solution	30 mg/1mL	Intramuscular; Intravenous; Subcutaneous	Hospira, Inc.	2005-11-18	2018-03-01
Talwin	Solution	30 mg	Intramuscular; Intravenous; Subcutaneous	Pfizer	2002-11-01	Not applicable
Talwin	Injection, solution	30 mg/1mL	Intramuscular; Intravenous; Subcutaneous	Hospira, Inc.	2005-09-30	2012-03-01
Talwin - Liq 30mg/ml	Liquid	30 mg	Intramuscular; Intravenous; Subcutaneous	Sanofi Synthelabo	1967-12-31	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Pentazocine and Naloxone	Pentazocine (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)	Tablet	Oral	Sun Pharmaceutical Industries Limited	2018-07-31	Not applicable
Pentazocine and Naloxone	Pentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)	Tablet	Oral	Golden State Medical Supply	2000-03-24	2018-10-11
Pentazocine and naloxone	Pentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)	Tablet	Oral	Keltman Pharmaceuticals Inc.	2009-07-21	Not applicable
Pentazocine and naloxone	Pentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)	Tablet	Oral	Pd Rx Pharmaceuticals, Inc.	1997-05-21	Not applicable
Pentazocine and naloxone	Pentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)	Tablet	Oral	bryant ranch prepack	1997-01-21	2018-06-05
Pentazocine and naloxone	Pentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)	Tablet	Oral	Lake Erie Medical &Surgical Supply Dba Quality Care Products Llc	1997-01-21	2014-12-31
Pentazocine and naloxone	Pentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)	Tablet	Oral	Actavis Pharma, Inc.	1997-05-21	Not applicable
Pentazocine and naloxone hydrochlorides	Pentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)	Tablet	Oral	Actavis Totowa LLC	2001-07-01	2008-08-20
Pentazocine HCl and Acetaminophen	Pentazocine Hydrochloride (25 mg/1) + Acetaminophen (650 mg/1)	Tablet	Oral	Actavis Pharma Company	2000-03-24	2015-03-31
Pentazocine HCl and Acetaminophen	Pentazocine Hydrochloride (25 mg/1) + Acetaminophen (650 mg/1)	Tablet	Oral	Rebel Distributors	2000-03-24	Not applicable

International/Other Brands

Fortal (Sanofi-Aventis) / Fortral (Sanofi-Aventis) / Fortwin (Terapia) / Pangon (L.B.S.) / Pentagin (Daiichi Sankyo) / Sosegon (Sanofi-Aventis) / Stopain (Beximco) / Talwin PX (Sanofi-Aventis)

Categories

UNII

768DQ5A5AI

CAS number

359-83-1

Weight

Average: 285.4238
Monoisotopic: 285.209264491

Chemical Formula

C₁₉H₂₇NO

InChI Key

VOKSWYLNZZRQPF-GDIGMMSISA-N

InChI

InChI=1S/C19H27NO/c1-13(2)7-9-20-10-8-19(4)14(3)18(20)11-15-5-6-16(21)12-17(15)19/h5-7,12,14,18,21H,8-11H2,1-4H3/t14-,18+,19+/m0/s1

IUPAC Name

(1R,9R,13R)-1,13-dimethyl-10-(3-methylbut-2-en-1-yl)-10-azatricyclo[7.3.1.0²,⁷]trideca-2,4,6-trien-4-ol

SMILES

C[C@H]1[C@H]2CC3=CC=C(O)C=C3[C@]1(C)CCN2CC=C(C)C

Pharmacology

Indication

For the relief of moderate to severe pain.

Associated Conditions

Associated Therapies

Preanesthetic medication therapy

Pharmacodynamics

Pentazocine is a potent analgesic which when administered orally in a 50 mg dose appears equivalent in analgesic effect to 60 mg (1 grain) of codeine. Onset of significant analgesia usually occurs between 15 and 30 minutes after oral administration, and duration of action is usually three hours or longer. Onset and duration of action and the degree of pain relief are related both to dose and the severity of pretreatment pain. Pentazocine weakly antagonizes the analgesic effects of morphine and meperidine; in addition, it produces incomplete reversal of cardiovascular, respiratory, and behavioral depression induced by morphine and meperidine. Pentazocine has about 1/50 the antagonistic activity of nalorphine. It also has sedative activity.

Mechanism of action

The preponderance of evidence suggests that pentazocine antagonizes the opioid effects by competing for the same receptor sites, especially the opioid mu receptor.

Target	Actions	Organism
AMu-type opioid receptor	antagonist	Humans
AKappa-type opioid receptor	agonist	Humans
ASigma non-opioid intracellular receptor 1	agonist	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Well absorbed from the gastro-intestinal tract.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Hepatic

Route of elimination

Not Available

Half life

2 to 3 hours

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Pathway	Category
Pentazocine Action Pathway	Drug action

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
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2,5-Dimethoxy-4-ethylamphetamine	2,5-Dimethoxy-4-ethylamphetamine may increase the analgesic activities of Pentazocine.
2,5-Dimethoxy-4-ethylthioamphetamine	2,5-Dimethoxy-4-ethylthioamphetamine may increase the analgesic activities of Pentazocine.
4-Bromo-2,5-dimethoxyamphetamine	4-Bromo-2,5-dimethoxyamphetamine may increase the analgesic activities of Pentazocine.
4-Methoxyamphetamine	The risk or severity of adverse effects can be increased when Pentazocine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamine	The risk or severity of adverse effects can be increased when Pentazocine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-Nitroindazole	The risk or severity of adverse effects can be increased when Pentazocine is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	The risk or severity of adverse effects can be increased when Pentazocine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Pentazocine.
Acebutolol	The serum concentration of Acebutolol can be increased when it is combined with Pentazocine.
Acepromazine	The risk or severity of hypotension and CNS depression can be increased when Acepromazine is combined with Pentazocine.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Take without regard to meals. Avoid alcohol.

References

General References

Not Available

External Links

Human Metabolome Database: HMDB0014790
KEGG Drug: D00498
KEGG Compound: C07421
PubChem Compound: 441278
PubChem Substance: 46506363
ChemSpider: 390041
BindingDB: 50001028
ChEBI: 7982
ChEMBL: CHEMBL560
Therapeutic Targets Database: DAP000356
PharmGKB: PA164744326
Guide to Pharmacology: GtP Drug Page
Wikipedia: Pentazocine

ATC Codes

N02AD01 — Pentazocine

AHFS Codes

28:08.12 — Opiate Partial Agonists

MSDS

Download (48.4 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Treatment	Treatment of Menopausal Hot Flashes	1
2	Completed	Treatment	Bipolar Disorder (BD)	1
2	Completed	Treatment	Bipolar Disorder (BD) / Mania / Manic Disorder / Manic syndromes / Schizoaffective Disorders	1
4	Unknown Status	Treatment	Anaesthesia therapy / Pregnancy Termination	1
Not Available	Completed	Treatment	Headaches / Migraine	1

Pharmacoeconomics

Manufacturers

Sanofi aventis us llc
Hospira inc

Packagers

A-S Medication Solutions LLC
Dispensing Solutions
Diversified Healthcare Services Inc.
Hospira Inc.
Kaiser Foundation Hospital
Keltman Pharmaceuticals Inc.
Mallinckrodt Inc.
Nucare Pharmaceuticals Inc.
Ohm Laboratories Inc.
PD-Rx Pharmaceuticals Inc.
Pharmedix
Physicians Total Care Inc.
Ranbaxy Laboratories
Rebel Distributors Corp.
Sanofi-Aventis Inc.
Southwood Pharmaceuticals
Stat Rx Usa
Watson Pharmaceuticals

Dosage forms

Form	Route	Strength
Tablet	Oral
Injection, solution	Intramuscular; Intravenous; Subcutaneous	30 mg/1mL
Solution	Intramuscular; Intravenous; Subcutaneous	30 mg
Tablet	Oral	50 mg
Liquid	Intramuscular; Intravenous; Subcutaneous	30 mg

Prices

Unit description	Cost	Unit
Talwin 30 mg/ml vial	14.78USD	ml
Talwin 30 mg/ml ampul	4.86USD	ml
Talwin 30 mg/ml	1.64USD	ml
Talwin 50 mg Tablet	0.47USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	146.3 °C	PhysProp
logP	4.64	DAYLIGHT (1999)
pKa	8.88	SANGSTER (1994)

Predicted Properties

Property	Value	Source
Water Solubility	0.122 mg/mL	ALOGPS
logP	4.44	ALOGPS
logP	3.89	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.59	ChemAxon
pKa (Strongest Basic)	12.4	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	23.47 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.8 m³·mol^-1	ChemAxon
Polarizability	33.86 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9931
Blood Brain Barrier	+	0.9769
Caco-2 permeable	+	0.7902
P-glycoprotein substrate	Substrate	0.9014
P-glycoprotein inhibitor I	Inhibitor	0.8563
P-glycoprotein inhibitor II	Inhibitor	0.6975
Renal organic cation transporter	Inhibitor	0.6982
CYP450 2C9 substrate	Non-substrate	0.7947
CYP450 2D6 substrate	Substrate	0.8919
CYP450 3A4 substrate	Substrate	0.7819
CYP450 1A2 substrate	Inhibitor	0.5886
CYP450 2C9 inhibitor	Non-inhibitor	0.8321
CYP450 2D6 inhibitor	Inhibitor	0.8147
CYP450 2C19 inhibitor	Non-inhibitor	0.8585
CYP450 3A4 inhibitor	Non-inhibitor	0.8155
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.778
Ames test	Non AMES toxic	0.8231
Carcinogenicity	Non-carcinogens	0.9322
Biodegradation	Not ready biodegradable	0.9888
Rat acute toxicity	2.4411 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Strong inhibitor	0.6301
hERG inhibition (predictor II)	Inhibitor	0.5

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Description: This compound belongs to the class of organic compounds known as 2,6-dimethyl-3-benzazocines. These are aromatic compounds containing a 6,7-benzomorphan skeleton, which is substituted by methyl group at the 2- and 6-positions.
Kingdom: Organic compounds
Super Class: Alkaloids and derivatives
Class: 6,7-benzomorphans
Sub Class: 2,6-dimethyl-3-benzazocines
Direct Parent: 2,6-dimethyl-3-benzazocines
Alternative Parents: 4-hydroxy-6,7-benzomorphans / Benzazocines / Tetralins / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Piperidines / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organooxygen compoundsHydrocarbon derivatives
show 1 more
Substituents: 2,6-dimethyl-3-benzazocine / 4-hydroxy-6,7-benzomorphan / Benzazocine / Tetralin / 1-hydroxy-2-unsubstituted benzenoid / Aralkylamine / Piperidine / Benzenoid / Tertiary amine / Tertiary aliphatic amine
show 10 more
Molecular Framework: Aromatic heteropolycyclic compounds
External Descriptors: benzazocine (CHEBI:7982)

Targets

Details1. Mu-type opioid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Voltage-gated calcium channel activity
Specific Function: Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name: OPRM1
Uniprot ID: P35372
Uniprot Name: Mu-type opioid receptor
Molecular Weight: 44778.855 Da

References

Levine JD, Gordon NC: Synergism between the analgesic actions of morphine and pentazocine. Pain. 1988 Jun;33(3):369-72. [PubMed:3419842]
Martin BR, Katzen JS, Woods JA, Tripathi HL, Harris LS, May EL: Stereoisomers of [3H]-N-allylnormetazocine bind to different sites in mouse brain. J Pharmacol Exp Ther. 1984 Dec;231(3):539-44. [PubMed:6094791]
Kamei J, Iwamoto Y, Misawa M, Nagase H, Kasuya Y: Effects of diabetes on the antinociceptive effect of (+/-)pentazocine in mice. Res Commun Chem Pathol Pharmacol. 1994 Apr;84(1):105-10. [PubMed:8042002]
Picker MJ, Benyas S, Horwitz JA, Thompson K, Mathewson C, Smith MA: Discriminative stimulus effects of butorphanol: influence of training dose on the substitution patterns produced by Mu, Kappa and Delta opioid agonists. J Pharmacol Exp Ther. 1996 Dec;279(3):1130-41. [PubMed:8968334]
Saha N, Datta H, Sharma PL: Effects of morphine, buprenorphine, pentazocine and nalorphine on acquisition and extinction of active avoidance responses in rats. Indian J Physiol Pharmacol. 1990 Jul;34(3):179-82. [PubMed:2286420]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	2.2	N/A	N/A	9686407

Details2. Kappa-type opioid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Opioid receptor activity
Specific Function: G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name: OPRK1
Uniprot ID: P41145
Uniprot Name: Kappa-type opioid receptor
Molecular Weight: 42644.665 Da

References

Chien CC, Pasternak GW: (-)-Pentazocine analgesia in mice: interactions with a sigma receptor system. Eur J Pharmacol. 1995 Dec 27;294(1):303-8. [PubMed:8788445]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	3.1	N/A	N/A	8360875
Ki (nM)	3.8	N/A	N/A	8098066

Details3. Sigma non-opioid intracellular receptor 1

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Agonist

General Function: Opioid receptor activity
Specific Function: Functions in lipid transport from the endoplasmic reticulum and is involved in a wide array of cellular functions probably through regulation of the biogenesis of lipid microdomains at the plasma m...
Gene Name: SIGMAR1
Uniprot ID: Q99720
Uniprot Name: Sigma non-opioid intracellular receptor 1
Molecular Weight: 25127.52 Da

References

Chien CC, Pasternak GW: (-)-Pentazocine analgesia in mice: interactions with a sigma receptor system. Eur J Pharmacol. 1995 Dec 27;294(1):303-8. [PubMed:8788445]
Colabufo NA, Contino M, Inglese C, Niso M, Perrone R, Roperto S, Roperto F: In vitro and ex vivo characterization of sigma-1 and sigma-2 receptors: agonists and antagonists in biological assays. Cent Nerv Syst Agents Med Chem. 2009 Sep;9(3):161-71. [PubMed:20021350]
Dun Y, Thangaraju M, Prasad P, Ganapathy V, Smith SB: Prevention of excitotoxicity in primary retinal ganglion cells by (+)-pentazocine, a sigma receptor-1 specific ligand. Invest Ophthalmol Vis Sci. 2007 Oct;48(10):4785-94. [PubMed:17898305]
Mamolo MG, Zampieri D, Zanette C, Florio C, Collina S, Urbano M, Azzolina O, Vio L: Substituted benzylaminoalkylindoles with preference for the sigma2 binding site. Eur J Med Chem. 2008 Oct;43(10):2073-81. Epub 2007 Sep 26. [PubMed:18069094]
Pal A, Hajipour AR, Fontanilla D, Ramachandran S, Chu UB, Mavlyutov T, Ruoho AE: Identification of regions of the sigma-1 receptor ligand binding site using a novel photoprobe. Mol Pharmacol. 2007 Oct;72(4):921-33. Epub 2007 Jul 10. [PubMed:17622576]

Drug created on June 13, 2005 07:24 / Updated on July 16, 2019 06:23

Pentazocine

Identification

Structure for Pentazocine (DB00652)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References

References