Identification
- Summary
Pentazocine is an analgesic used to treat moderate to severe pain.
- Generic Name
- Pentazocine
- DrugBank Accession Number
- DB00652
- Background
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)
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Pentazocine (DB00652)
- Weight
- Average: 285.431
Monoisotopic: 285.209264493 - Chemical Formula
- C19H27NO
- Synonyms
- Pentazocin
- Pentazocina
- Pentazocine
- Pentazocinum
- External IDs
- CS 350
- NIH 7958
- Win 20228
Pharmacology
- Indication
For the relief of moderate to severe pain.
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- Associated Therapies
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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 ASigma non-opioid intracellular receptor 1 agonistHumans AMu-type opioid receptor antagonistHumans AKappa-type opioid receptor agonistHumans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
Pathway Category Pentazocine Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Pentazocine is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Pentazocine is combined with Acetazolamide. Acetophenazine The risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Pentazocine. Aclidinium The risk or severity of adverse effects can be increased when Aclidinium is combined with Pentazocine. Agomelatine The risk or severity of CNS depression can be increased when Pentazocine is combined with Agomelatine. Alfentanil The therapeutic efficacy of Alfentanil can be decreased when used in combination with Pentazocine. Alimemazine The risk or severity of hypotension and CNS depression can be increased when Alimemazine is combined with Pentazocine. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Pentazocine. Almotriptan The risk or severity of CNS depression can be increased when Pentazocine is combined with Almotriptan. Alosetron The risk or severity of CNS depression can be increased when Pentazocine is combined with Alosetron. 
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- Avoid alcohol.
- Take with or without food. Food does not significantly affect absorption.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Pentazocine hydrochloride A36BXO4PPX 64024-15-3 OQGYMIIFOSJQSF-UHFFFAOYSA-N Pentazocine lactate 1P2XIB510O 17146-95-1 QNLDTXPVZPRSAM-UHFFFAOYSA-N - 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)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Talwin Injection, solution 30 mg/1mL Intramuscular; Intravenous; Subcutaneous Physicians Total Care, Inc. 1995-12-20 2001-06-30 US 
Talwin Tablet 50 mg Oral Sanofi Aventis 1970-12-31 2021-02-19 Canada 
Talwin Injection, solution 30 mg/1mL Intramuscular; Intravenous; Subcutaneous Hospira, Inc. 2005-09-30 2012-03-01 US Talwin Injection, solution 30 mg/1mL Intramuscular; Intravenous; Subcutaneous Hospira, Inc. 2006-10-06 2006-11-09 US Talwin Solution 30 mg / 1 mL Intramuscular; Intravenous; Subcutaneous Pfizer Canada Ulc 2002-11-01 2019-11-21 Canada Talwin Injection, solution 30 mg/1mL Intramuscular; Intravenous; Subcutaneous Hospira, Inc. 2005-11-18 2018-03-01 US Talwin Injection, solution 30 mg/1mL Intramuscular; Intravenous; Subcutaneous General Injectables & Vaccines 2010-08-01 2017-01-18 US Talwin - Liq 30mg/ml Liquid 30 mg / mL Intramuscular; Intravenous; Subcutaneous Sanofi Synthelabo 1967-12-31 2001-08-10 Canada - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 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 US Pentazocine and naloxone Pentazocine hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1) Tablet Oral PD-Rx Pharmaceuticals, Inc. 1997-05-21 2018-11-08 US Pentazocine and Naloxone Pentazocine hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1) Tablet Oral Golden State Medical Supply, Inc. 2000-03-24 2017-01-02 US Pentazocine and Naloxone Pentazocine (50 mg/1) + Naloxone hydrochloride (0.5 mg/1) Tablet Oral Sun Pharmaceutical Industries Limited 2018-07-31 Not applicable US Pentazocine and naloxone Pentazocine hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1) Tablet Oral Keltman Pharmaceuticals Inc. 2009-07-21 Not applicable US Pentazocine and naloxone Pentazocine hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1) Tablet Oral bryant ranch prepack 1997-05-21 2017-05-30 US Pentazocine and naloxone Pentazocine hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1) Tablet Oral Actavis Pharma, Inc. 1997-05-21 Not applicable US 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 US Pentazocine HCl and Acetaminophen Pentazocine hydrochloride (25 mg/1) + Acetaminophen (650 mg/1) Tablet Oral Rebel Distributors 2000-03-24 Not applicable US Pentazocine HCl and Acetaminophen Pentazocine hydrochloride (25 mg/1) + Acetaminophen (650 mg/1) Tablet Oral Actavis Pharma Company 2000-03-24 2015-03-31 US
Categories
- ATC Codes
- N02AD01 — Pentazocine
- Drug Categories
- Adjuvants, Anesthesia
- Agents that reduce seizure threshold
- Alkaloids
- Analgesics
- Benzomorphan Derivatives
- Benzomorphans
- Central Nervous System Agents
- Central Nervous System Depressants
- Heterocyclic Compounds, Fused-Ring
- Mixed Agonist / Antagonist Opioids
- Morphinans
- Narcotics
- Nervous System
- Opiate Alkaloids
- Opiate Partial Agonists
- Opioid Antagonists
- Opioids
- P-glycoprotein substrates
- Partial Opioid Agonist/Antagonist
- Peripheral Nervous System Agents
- Phenanthrenes
- Sensory System Agents
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Classification
- Not classified
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- RP4A60D26L
- CAS number
- 359-83-1
- InChI Key
- VOKSWYLNZZRQPF-UHFFFAOYSA-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
- IUPAC Name
- 1,13-dimethyl-10-(3-methylbut-2-en-1-yl)-10-azatricyclo[7.3.1.0^{2,7}]trideca-2(7),3,5-trien-4-ol
- SMILES
- CC1C2CC3=C(C=C(O)C=C3)C1(C)CCN2CC=C(C)C
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0243543
- KEGG Drug
- D00498
- KEGG Compound
- C07421
- PubChem Compound
- 441278
- PubChem Substance
- 46506363
- ChemSpider
- 4574
- BindingDB
- 50032403
- 8001
- ChEBI
- 182080
- ChEMBL
- CHEMBL100116
- ZINC
- ZINC000000000596
- Therapeutic Targets Database
- DAP000356
- PharmGKB
- PA164744326
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Pentazocine
- MSDS
- Download (48.4 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Pain 1 4 Unknown Status Treatment Anesthesia therapy / Medically induced abortion 1 2 Completed Treatment Bipolar Disorder (BD) 1 2 Completed Treatment Bipolar Disorder (BD) / Mania / Manic Disorder / Manic syndromes / Schizoaffective Disorders 1 1 Completed Treatment Treatment of Menopausal Hot Flashes 1 Not Available Completed Supportive Care Acute Post-operative Pain Following Caesarean Section 1 Not Available Completed Treatment Headache / 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 Suppository Injection, solution Subcutaneous Tablet Oral Injection Injection, solution Intramuscular; Intravenous; Subcutaneous Injection, solution Intramuscular; Intravenous; Subcutaneous 30 mg/1mL Solution Intramuscular; Intravenous; Subcutaneous 30 mg / 1 mL Tablet Oral 50 mg Liquid Intramuscular; Intravenous; Subcutaneous 30 mg / mL Tablet Oral - 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) 10.42 Chemaxon pKa (Strongest Basic) 9.57 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 33.97 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Not Available
Targets
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- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Moriki Y, Suzuki T, Fukami T, Hanano M, Tomono K, Watanabe J: Involvement of P-glycoprotein in blood-brain barrier transport of pentazocine in rats using brain uptake index method. Biol Pharm Bull. 2004 Jun;27(6):932-5. doi: 10.1248/bpb.27.932. [Article]
- Moriki Y, Suzuki T, Furuishi T, Fukami T, Tomono K, Watanabe J: In vivo evidence for the efflux transport of pentazocine from the brain across the blood-brain barrier using the brain efflux index method. J Drug Target. 2005 Jan;13(1):53-9. doi: 10.1080/10611860400024110. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 03, 2023 08:16