U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C19H27NO
Molecular Weight 285.4245
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENTAZOCINE

SMILES

CC(=CCN1CC[C@]2(C)[C@@]([H])(C)[C@@]1([H])Cc3ccc(cc32)O)C

InChI

InChIKey=VOKSWYLNZZRQPF-GDIGMMSISA-N
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

HIDE SMILES / InChI

Description
Curator's Comment:: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12379919 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/016194s079s080lbl.pdf | https://www.drugbank.ca/drugs/DB00652

Pentazocine is a synthetically prepared prototypical mixed agonist-antagonist narcotic (opioid analgesic) drug of the benzomorphan class of opioids used to treat moderate to moderately severe pain. Pentazocine is sold under several brand names, such as Fortral, Sosegon, Talwin NX. Pentazocine acts as an agonist of κ-opioid receptors and as an antagonist of μ-opioid receptors. This compound may exist as one of two enantiomers, named (+)-pentazocine and (−)-pentazocine. Side effects are similar to those of morphine, but pentazocine, due to its action at the kappa opioid receptor is more likely to invoke psychotomimetic effects. High dose may cause high blood pressure or high heart rate.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.9 nM [Ki]
75.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TALWIN

Approved Use

Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for the relief of moderate to severe pain. Pentazocine Hydrochloride and Naloxone Hydrochloride Tablets, USP is indicated for oral use only.

Launch Date

-7.7068796E10
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
227 ng/mL
80 mg single, intramuscular
dose: 80 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PENTAZOCINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
102 ng/mL
40 mg single, intramuscular
dose: 40 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PENTAZOCINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1311 ng × h/mL
80 mg single, intramuscular
dose: 80 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PENTAZOCINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
536 ng × h/mL
40 mg single, intramuscular
dose: 40 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PENTAZOCINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.3 h
80 mg single, intramuscular
dose: 80 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PENTAZOCINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.6 h
40 mg single, intramuscular
dose: 40 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
PENTAZOCINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Sources:
unhealthy
Disc. AE: Respiratory depression, Hypotension...
AEs leading to
discontinuation/dose reduction:
Respiratory depression
Hypotension (severe)
Sources:
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Co-administed with::
benzodiazepines
Sources:
unhealthy
Disc. AE: Sedation, Coma...
AEs leading to
discontinuation/dose reduction:
Sedation
Coma
Sources:
AEs

AEs

AESignificanceDosePopulation
Respiratory depression Disc. AE
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Sources:
unhealthy
Hypotension severe
Disc. AE
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Sources:
unhealthy
Coma Disc. AE
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Co-administed with::
benzodiazepines
Sources:
unhealthy
Sedation Disc. AE
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Co-administed with::
benzodiazepines
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as victim

Drug as victim

Tox targets

Tox targets

PubMed

PubMed

TitleDatePubMed
Clinical effects of pentazocine in hospitalized medical patients.
1975 Feb-Mar
Mental and emotional disturbance with pentazocine (Talwin) use.
1975 Jul
Letter: Pentazocine-induced fibrous myopathy.
1975 Jun 16
Iatrogenic muscle fibrosis. Arm levitation as an initial sign.
1975 Nov 10
WHO Expert Committee on Drug Dependence. Thirty-second report.
2001
Phencyclidine impairs latent learning in mice: interaction between glutamatergic systems and sigma(1) receptors.
2001 Apr
Molecular cloning and pharmacological characterization of the rat sigma1 receptor.
2001 Aug 1
[Opioid tolerance and dependence--pharmacological aspects].
2001 Jul-Sep
Subjective, psychomotor, and physiological effects of cumulative doses of mixed-action opioids in healthy volunteers.
2001 Jun
TRK-820, a selective kappa-opioid agonist, produces potent antinociception in cynomolgus monkeys.
2001 Mar
A multireceptorial binding reinvestigation on an extended class of sigma ligands: N-[omega-(indan-1-yl and tetralin-1-yl)alkyl] derivatives of 3,3-dimethylpiperidine reveal high affinities towards sigma1 and EBP sites.
2001 May
Oxygen saturation in healthy newborn infants immediately after birth measured by pulse oximetry.
2002 Apr
Sigma(2)-receptor regulation of dopamine transporter via activation of protein kinase C.
2002 Apr
Application of gas chromatography-surface ionization organic mass spectrometry to forensic toxicology.
2002 Aug 25
[Biopharmaceutical studies on molecular mechanisms of membrane transport].
2002 Dec
[Sedation analgesia in interventional radiology].
2002 Feb
Pharmacological treatment of postoperative shivering: a quantitative systematic review of randomized controlled trials.
2002 Feb
Substance abuse monitoring by the Correctional Service of Canada.
2002 Feb
Binding of sigma receptor ligands and their effects on muscarine-induced Ca(2+) changes in SH-SY5Y cells.
2002 Feb 1
Renal amyloidosis in a pentazocine addict.
2002 Jul
Fibromyositis after intramuscular pentazocine abuse.
2002 Jul-Sep
Synthesis of (+)-cis-N-(4-isothiocyanatobenzyl)-N-normetazocine, an isothiocyanate derivative of N-benzylnormetazocine as acylant agent for the sigma(1) receptor.
2002 Jun 6
Investigation on the influx transport mechanism of pentazocine at the blood-brain barrier in rats using the carotid injection technique.
2002 Oct
Myocardial protection by anesthetic agents against ischemia-reperfusion injury: an update for anesthesiologists.
2002 Oct
Antidiarrhoeal properties of a novel sigma ligand (JO 2871) on toxigenic diarrhoea in mice: mechanisms of action.
2002 Oct
Development and use of a computer program to detect potentially inappropriate prescribing in older adults residing in Canadian long-term care facilities.
2002 Oct 14
Demographics, assessment and management of pain in the elderly.
2003
Agonist/antagonist properties of nalbuphine, butorphanol and (-)-pentazocine in male vs. female rats.
2003 Apr
Permanently oriented antibody immobilization for digoxin determination with a flow-through fluoroimmunosensor.
2003 Apr
Intracellular dynamics of sigma-1 receptors (sigma(1) binding sites) in NG108-15 cells.
2003 Aug
Postoperative pain management following caesarean section in University of Ilorin Teaching Hospital (UITH), Ilorin, Nigeria.
2003 Dec
Differential effects of agonists on adenylyl cyclase superactivation mediated by the kappa opioid receptors: adenylyl cyclase superactivation is independent of agonist-induced phosphorylation, desensitization, internalization, and down-regulation.
2003 Dec
Gabapentin in the management of pentazocine dependence: a potent analgesic--anticraving agent.
2003 Jul
Opioid prescription for terminally ill outpatients in a district of northern Italy: a retrospective survey.
2003 Jul
Analgesic activity of Piper longum Linn. root.
2003 Jun
Different brain kinetics of two sigma 1 receptor ligands, [3H](+)-pentazocine and [11C]SA4503, by P-glycoprotein modulation.
2003 May
Opioid agonists have different efficacy profiles for G protein activation, rapid desensitization, and endocytosis of mu-opioid receptors.
2003 May 23
Dose ratio is important in maximizing naloxone enhancement of nalbuphine analgesia in humans.
2003 Nov 6
The sigma receptor ligand (+)-pentazocine prevents apoptotic retinal ganglion cell death induced in vitro by homocysteine and glutamate.
2004 Apr 7
Antiproliferative and cytotoxic effects of some sigma2 agonists and sigma1 antagonists in tumour cell lines.
2004 Aug
Delta-opioid receptor agonist reduces severity of postresuscitation myocardial dysfunction.
2004 Aug
Pentazocine-induced cutaneous sclerosis and panniculitis in an Indian male.
2004 Jul
Sternoclavicular septic arthritis: review of 180 cases.
2004 May
Experimental pain models reveal no sex differences in pentazocine analgesia in humans.
2004 May
Using mixed agonist-antagonists.
2005 Feb
Patents

Sample Use Guides

In Vivo Use Guide
Initial dose: 30 mg by intramuscular, subcutaneous, or intravenous route. This may be repeated every 3 to 4 hours. Doses in excess of 30 mg intravenously or 60 mg intramuscularly or subcutaneously are not recommended. Maximum daily dose: 360 mg
Route of Administration: Other
Cultured bovine adrenal medullary cells (1 × 10^6 / well) or SK-N-SH cells (0.3 × 10^6 / well) were preincubated with or without PTZ (Pentazocine) for the indicated times and further incubated at 37°C for another 12 min in KRH buffer containing 100 μM pargyline, 1 mM ascorbic acid, and [3H]NE (500 or 100 nM, respectively, 0.1 μCi) in the presence or absence of desipramine and PTZ. KRH buffer was composed of 154 mM NaCl, 5.6 mM KCl, 1.1 mM MgSO4, 2.2 mM CaCl2, 10 mM HEPES-Tris, and 10 mM glucose, adjusted to pH 7.4. After incubation, the cells were rapidly washed three times with 250 μl of ice-cold KRH buffer and solubilized in 500 μl of 10% Triton X-100. The radioactivity in the solubilized cells was counted with a liquid scintillation counter.
Name Type Language
PENTAZOCINE
EP   HSDB   INN   MART.   MI   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
(+/-)-PENTAZOCINE
Common Name English
TALWIN
Brand Name English
PENTAZOCINE [JAN]
Common Name English
PENTAZOCINE [EP]
Common Name English
PENTAZOCINE [WHO-DD]
Common Name English
PENTAZOCINE [HSDB]
Common Name English
PENTAZOCINE [MART.]
Common Name English
CIS-(+/-)-PENTAZOCINE
Common Name English
NSC-107430
Code English
WIN 20,228
Code English
DL-PENTAZOCINE
Common Name English
NIH-7958
Code English
2,6-METHANO-3-BENZAZOCIN-8-OL, 1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(3-METHYL-2-BUTEN-1-YL)-, (2R,6R,11R)-REL-
Common Name English
PENTAZOCINE [VANDF]
Common Name English
PENTAZOCINE [INN]
Common Name English
PENTAZOCINE CIV
USP-RS  
Common Name English
2,6-METHANO-3-BENZAZOCIN-8-OL, 1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(3-METHYL-2-BUTENYL)-, (2.ALPHA.,6.ALPHA.,11R*)-
Common Name English
WIN-20228
Code English
PENTAZOCINE CIV [USP-RS]
Common Name English
(2R*,6R*,11R*)-1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(3-METHYL-2-BUTENYL)-2,6-METHANO-3-BENZAZOCIN-8-OL
Common Name English
PENTAZOCINE [USP]
Common Name English
PENTAZOCINE [EP MONOGRAPH]
Common Name English
PENTAZOCINE [USAN]
Common Name English
PENTAZOCINE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
WHO-VATC QN02AD01
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
LIVERTOX 756
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
NDF-RT N0000175686
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
WHO-ATC N02AD01
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
DEA NO. 9709
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
NDF-RT N0000175685
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
NCI_THESAURUS C1506
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
NDF-RT N0000175688
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
Code System Code Type Description
DRUG CENTRAL
3424
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY
MESH
D010423
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY
HSDB
3150
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY
MERCK INDEX
M8503
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
PENTAZOCINE
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY
USP_CATALOG
1505007
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY USP-RS
DRUG BANK
DB00652
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY
FDA UNII
RP4A60D26L
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY
EVMPD
SUB09688MIG
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY
ChEMBL
CHEMBL560
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY
CAS
359-83-1
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY
LACTMED
Pentazocine
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY
INN
1674
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY
NCI_THESAURUS
C61884
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY
RXCUI
8001
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY RxNorm
ECHA (EC/EINECS)
206-634-6
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY
EPA CompTox
359-83-1
Created by admin on Fri Jun 25 21:19:39 UTC 2021 , Edited by admin on Fri Jun 25 21:19:39 UTC 2021
PRIMARY