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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Pentazocine
- Accession Number
- DB00652 (APRD01173)
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Description
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
Structure for Pentazocine (DB00652)
- 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 Unlock Additional DataTalwin Solution 30 mg 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 Hospira, Inc. 2005-09-30 2012-03-01 US Talwin Injection, solution 30 mg/1mL Intramuscular; Intravenous; Subcutaneous General Injectables & Vaccines 2010-08-01 2017-01-18 US Talwin Injection, solution 30 mg/1mL Intramuscular; Intravenous; Subcutaneous Physicians Total Care, Inc. 1995-12-20 2001-06-30 US Talwin Injection, solution 30 mg/1mL Intramuscular; Intravenous; Subcutaneous Hospira, Inc. 2006-10-06 2006-11-09 US Talwin Tablet Oral Sanofi Aventis 1970-12-31 Not applicable Canada Talwin - Liq 30mg/ml Liquid Intramuscular; Intravenous; Subcutaneous Sanofi Synthelabo 1967-12-31 2001-08-10 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End 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 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 Actavis Pharma, Inc. 1997-05-21 Not applicable 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 Pd Rx Pharmaceuticals, Inc. 1997-05-21 Not applicable US 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 bryant ranch prepack 1997-01-21 2018-06-05 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 - 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
- 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
- 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
- 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 antagonistHumans AKappa-type opioid receptor agonistHumans ASigma non-opioid intracellular receptor 1 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
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Pentazocine Action Pathway Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Unlock Additional Data
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.
Learn more 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.
Learn more 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.
Learn moreInteractions
- 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 Unlock Additional Data2,5-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. Acepromazine The risk or severity of hypotension and CNS depression can be increased when Acepromazine is combined with Pentazocine. Aceprometazine The risk or severity of hypotension and CNS depression can be increased when Aceprometazine is combined with Pentazocine. Acetazolamide The risk or severity of adverse effects can be increased when Pentazocine is combined with Acetazolamide. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Avoid alcohol.
- Take with or without food. Food does not significantly affect absorption.
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
- RxNav
- 8001
- ChEBI
- 7982
- ChEMBL
- CHEMBL560
- 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
- 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 Completed Treatment Pain 1 4 Unknown Status Treatment Anaesthesia therapy / Pregnancy Termination 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 Tablet Oral Injection, solution Intramuscular; Intravenous; Subcutaneous 30 mg/1mL Solution Intramuscular; Intravenous; Subcutaneous 30 mg Tablet Oral Liquid Intramuscular; Intravenous; Subcutaneous - 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
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 compounds 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
- 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]
- 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]
- 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]
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. [PubMed:15187451]
- 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. [PubMed:15848954]
Drug created on June 13, 2005 07:24 / Updated on March 30, 2020 22:56
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