Pentazocine

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
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 Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofSevere pain••••••••••••
Used in combination to manageSevere painCombination Product in combination with: Naloxone (DB01183)••••••••••••
Used in combination to manageMild painCombination Product in combination with: Acetaminophen (DB00316)••••••••••••
Management ofModerate pain••••••••••••
Used in combination to manageModerate painCombination Product in combination with: Acetaminophen (DB00316)••••••••••••
Associated Therapies
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
ASigma non-opioid intracellular receptor 1
agonist
Humans
AMu-type opioid receptor
antagonist
Humans
AKappa-type opioid receptor
agonist
Humans
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
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Toxicity

Not Available

Pathways
PathwayCategory
Pentazocine Action PathwayDrug 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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Pentazocine is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of CNS depression can be increased when Pentazocine is combined with Acetazolamide.
AcetophenazineThe risk or severity of hypotension and CNS depression can be increased when Acetophenazine is combined with Pentazocine.
AclidiniumThe risk or severity of adverse effects can be increased when Aclidinium is combined with Pentazocine.
AgomelatineThe risk or severity of CNS depression can be increased when Pentazocine is combined with Agomelatine.
Food Interactions
  • Avoid alcohol.
  • Take with or without food. Food does not significantly affect absorption.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Pentazocine hydrochlorideA36BXO4PPX64024-15-3OQGYMIIFOSJQSF-UHFFFAOYSA-N
Pentazocine lactate1P2XIB510O17146-95-1QNLDTXPVZPRSAM-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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
TalwinSolution30 mg / 1 mLIntramuscular; Intravenous; SubcutaneousPfizer Canada Ulc2002-11-012019-11-21Canada flag
TalwinInjection, solution30 mg/1mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.2005-09-302012-03-01US flag
TalwinInjection, solution30 mg/1mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.2006-10-062006-11-09US flag
TalwinTablet50 mgOralSanofi Aventis1970-12-312021-02-19Canada flag
TalwinInjection, solution30 mg/1mLIntramuscular; Intravenous; SubcutaneousGeneral Injectables & Vaccines2010-08-012017-01-18US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Pentazocine and naloxonePentazocine hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletOralPD-Rx Pharmaceuticals, Inc.1997-05-212018-11-08US flag
Pentazocine and NaloxonePentazocine hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletOralGolden State Medical Supply, Inc.2000-03-242017-01-02US flag
Pentazocine and naloxonePentazocine hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletOralKeltman Pharmaceuticals Inc.2009-07-21Not applicableUS flag
Pentazocine and NaloxonePentazocine (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletOralSun Pharmaceutical Industries Limited2018-07-31Not applicableUS flag
Pentazocine and naloxonePentazocine hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletOralbryant ranch prepack1997-05-212017-05-30US flag

Categories

ATC Codes
N02AD01 — Pentazocine
Drug Categories
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
Human Metabolome Database
HMDB0243543
KEGG Drug
D00498
KEGG Compound
C07421
PubChem Compound
441278
PubChem Substance
46506363
ChemSpider
4574
BindingDB
50032403
RxNav
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
PhaseStatusPurposeConditionsCount
4CompletedTreatmentPain1
4Unknown StatusTreatmentAnesthesia therapy / Medically induced abortion1
2CompletedTreatmentBipolar Disorder (BD)1
2CompletedTreatmentBipolar Disorder (BD) / Mania / Manic Disorder / Manic syndromes / Schizoaffective Disorders1
1CompletedTreatmentTreatment of Menopausal Hot Flashes1

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
FormRouteStrength
Suppository
TabletOral
Injection, solutionSubcutaneous
TabletOral
Injection
Injection, solutionIntramuscular; Intravenous; Subcutaneous
Injection, solutionIntramuscular; Intravenous; Subcutaneous30 mg/1mL
SolutionIntramuscular; Intravenous; Subcutaneous30 mg / 1 mL
TabletOral50 mg
LiquidIntramuscular; Intravenous; Subcutaneous30 mg / mL
Suppository50 MG
Prices
Unit descriptionCostUnit
Talwin 30 mg/ml vial14.78USD ml
Talwin 30 mg/ml ampul4.86USD ml
Talwin 30 mg/ml1.64USD ml
Talwin 50 mg Tablet0.47USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)146.3 °CPhysProp
logP4.64DAYLIGHT (1999)
pKa8.88SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.122 mg/mLALOGPS
logP4.44ALOGPS
logP3.89Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.42Chemaxon
pKa (Strongest Basic)9.57Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area23.47 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity89.8 m3·mol-1Chemaxon
Polarizability33.97 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9931
Blood Brain Barrier+0.9769
Caco-2 permeable+0.7902
P-glycoprotein substrateSubstrate0.9014
P-glycoprotein inhibitor IInhibitor0.8563
P-glycoprotein inhibitor IIInhibitor0.6975
Renal organic cation transporterInhibitor0.6982
CYP450 2C9 substrateNon-substrate0.7947
CYP450 2D6 substrateSubstrate0.8919
CYP450 3A4 substrateSubstrate0.7819
CYP450 1A2 substrateInhibitor0.5886
CYP450 2C9 inhibitorNon-inhibitor0.8321
CYP450 2D6 inhibitorInhibitor0.8147
CYP450 2C19 inhibitorNon-inhibitor0.8585
CYP450 3A4 inhibitorNon-inhibitor0.8155
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.778
Ames testNon AMES toxic0.8231
CarcinogenicityNon-carcinogens0.9322
BiodegradationNot ready biodegradable0.9888
Rat acute toxicity2.4411 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6301
hERG inhibition (predictor II)Inhibitor0.5
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-24670d7001b5411f65e2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-499e301d7fab3101f65a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gbi-2190000000-61f669e8d67971453659
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-7f1b680e1fbcbd607377
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0190000000-14ba0fa258d84fa63dd6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0k96-9210000000-fc9a203aff5dbd7fdf05
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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insights and accelerate drug research.
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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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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
  1. Levine JD, Gordon NC: Synergism between the analgesic actions of morphine and pentazocine. Pain. 1988 Jun;33(3):369-72. [Article]
  2. 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]
  3. 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]
  4. 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]
  5. 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
  1. 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
  1. 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]
  2. 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 March 18, 2024 16:48