Identification

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
Thumb
Synonyms
  • Pentazocin
  • Pentazocina
  • Pentazocine
  • Pentazocinum
External IDs
CS 350 / NIH 7958 / Win 20228
Product Ingredients
IngredientUNIICASInChI Key
Pentazocine HydrochlorideA36BXO4PPX64024-15-3OQGYMIIFOSJQSF-DTOXXUQYSA-N
Pentazocine Lactate1P2XIB510O17146-95-1QNLDTXPVZPRSAM-DTOXXUQYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
TalwinInjection, solution30 mg/1mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.2006-10-062006-11-09Us
TalwinTablet50 mgOralSanofi Aventis1970-12-31Not applicableCanada
TalwinInjection, solution30 mg/1mLIntramuscular; Intravenous; SubcutaneousGeneral Injectables & Vaccines2010-08-012017-01-18Us
TalwinSolution30 mgIntramuscular; Intravenous; SubcutaneousPfizer2002-11-01Not applicableCanada
TalwinInjection, solution30 mg/1mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.2005-11-182018-03-01Us
TalwinInjection, solution30 mg/1mLIntramuscular; Intravenous; SubcutaneousPhysicians Total Care, Inc.1995-12-202001-06-30Us
TalwinInjection, solution30 mg/1mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.2005-09-302012-03-01Us
Talwin - Liq 30mg/mlLiquid30 mgIntramuscular; Intravenous; SubcutaneousSanofi Synthelabo1967-12-31Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Pentazocine and naloxonePentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletOralKeltman Pharmaceuticals Inc.2009-07-21Not applicableUs
Pentazocine and naloxonePentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletOralPd Rx Pharmaceuticals, Inc.1997-05-21Not applicableUs
Pentazocine and naloxonePentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletOralLake Erie Medical &Surgical Supply Dba Quality Care Products Llc1997-01-212014-12-31Us
Pentazocine and NaloxonePentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletOralGolden State Medical Supply2000-03-242018-10-11Us
Pentazocine and naloxonePentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletOralActavis Pharma, Inc.1997-05-21Not applicableUs
Pentazocine and naloxonePentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletOralbryant ranch prepack1997-01-212018-06-05Us
Pentazocine and NaloxonePentazocine (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletOralSun Pharmaceutical Industries Limited2018-07-31Not applicableUs
Pentazocine and naloxone hydrochloridesPentazocine Hydrochloride (50 mg/1) + Naloxone hydrochloride (0.5 mg/1)TabletOralActavis Totowa LLC2001-07-012008-08-20Us
Pentazocine HCl and AcetaminophenPentazocine Hydrochloride (25 mg/1) + Acetaminophen (650 mg/1)TabletOralRebel Distributors2000-03-24Not applicableUs
Pentazocine HCl and AcetaminophenPentazocine Hydrochloride (25 mg/1) + Acetaminophen (650 mg/1)TabletOralActavis Pharma Company2000-03-242015-03-31Us
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
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
AMu-type opioid receptor
antagonist
Human
AKappa-type opioid receptor
agonist
Human
ASigma non-opioid intracellular receptor 1
agonist
Human
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
PathwayCategory
Pentazocine Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Pentazocine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Pentazocine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Pentazocine is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Pentazocine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Pentazocine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Pentazocine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Pentazocine is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of serotonin syndrome can be increased when Pentazocine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Pentazocine.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Pentazocine.
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
IUPHAR
1606
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
PhaseStatusPurposeConditionsCount
1CompletedTreatmentTreatment of Menopausal Hot Flashes1
2CompletedTreatmentBipolar Disorder (BD)1
2CompletedTreatmentBipolar Disorder (BD) / Mania / Manic Disorder / Manic syndromes / Schizoaffective Disorders1
4Unknown StatusTreatmentAnaesthesia therapy / Pregnancy Termination1
Not AvailableCompletedTreatmentHeadaches / Migraines1

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
TabletOral
Injection, solutionIntramuscular; Intravenous; Subcutaneous30 mg/1mL
SolutionIntramuscular; Intravenous; Subcutaneous30 mg
TabletOral50 mg
LiquidIntramuscular; Intravenous; Subcutaneous30 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)7.59ChemAxon
pKa (Strongest Basic)12.4ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity89.8 m3·mol-1ChemAxon
Polarizability33.86 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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot 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
Human
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. [PubMed:3419842]
  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. [PubMed:6094791]
  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. [PubMed:8042002]
  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. [PubMed:8968334]
  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. [PubMed:2286420]
Kind
Protein
Organism
Human
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. [PubMed:8788445]
Kind
Protein
Organism
Human
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. [PubMed:8788445]
  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. [PubMed:20021350]
  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. [PubMed:17898305]
  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. [PubMed:18069094]
  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. [PubMed:17622576]

Drug created on June 13, 2005 07:24 / Updated on November 20, 2018 00:45