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

Details

Stereochemistry RACEMIC
Molecular Formula C19H27NO.ClH
Molecular Weight 321.885
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENTAZOCINE HYDROCHLORIDE

SMILES

Cl.C[C@H]1[C@H]2CC3=CC=C(O)C=C3[C@]1(C)CCN2CC=C(C)C

InChI

InChIKey=OQGYMIIFOSJQSF-DTOXXUQYSA-N
InChI=1S/C19H27NO.ClH/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;1H/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

1967
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
Iatrogenic muscle fibrosis. Arm levitation as an initial sign.
1975 Nov 10
Pentazocine addict nephropathy: a case report.
1992 Mar
[The effect of ketamine on reducing postoperative agitation after sevoflurane anesthesia in pediatric strabismus surgery].
2002 Dec
[Biopharmaceutical studies on molecular mechanisms of membrane transport].
2002 Dec
Subarachnoid block for lower abdominal and lower limb surgery: UITH experience.
2002 Oct-Dec
Cardiovascular effects of intravenous pentazocine and cyclazocine in conscious, curarized-conscious, and anesthetized dogs.
2003
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
Efficacy of intrathecal morphine for analgesia following elective cesarean section: comparison with previous delivery.
2003 Aug
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
Enhanced sensitivity to the antinociceptive effects of kappa opioids in naltrexone-treated rats: dose- and time-dependent effects.
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
Effects of ethanol or rimcazole on dizocilpine maleate-induced behaviors in male and female rats.
2003 Feb
Age-related changes of the binding of [3h]SA4503 to sigma1 receptors in the rat brain.
2003 Feb
Sex differences in (-)-pentazocine antinociception: comparison to morphine and spiradoline in four rat strains using a thermal nociceptive assay.
2003 Feb
SR31747A is a sigma receptor ligand exhibiting antitumoural activity both in vitro and in vivo.
2003 Feb 10
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
Migratory hydroamination: a facile enantioselective synthesis of benzomorphans.
2003 Jul 23
Analgesic activity of Piper longum Linn. root.
2003 Jun
Role of kappa-opioid receptor activation in pharmacological preconditioning of swine.
2003 Jun
The analgesic effect of oral morphine or pentazocine for extracorporeal shock wave lithotripsy.
2003 Mar
[Neurochemical analysis and pharmacological regulation of the corticofugal control of the nociceptive signals in the afferent pathways].
2003 Mar-Apr
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
Modulation of Fas receptor proteins and dynamin during opiate addiction and induction of opiate withdrawal in rat brain.
2003 Nov
Dose ratio is important in maximizing naloxone enhancement of nalbuphine analgesia in humans.
2003 Nov 6
Generation and phenotypic analysis of sigma receptor type I (sigma 1) knockout mice.
2003 Oct
[Combined use of intrathecal morphine and diclofenac suppository for postoperative analgesia after caesarean section].
2003 Oct
Procaine hydrochloride fails to relieve pain in patients with acute pancreatitis.
2004
Effect of insulin hypoglycemic stress on nociceptive responses to mu- and kappa-opioid receptor agonists at LH-surge in female rats.
2004 Apr
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
[Intermittent complete left bundle branch block during general anesthesia].
2004 Dec
Molecular modeling of sigma 1 receptor ligands: a model of binding conformational and electrostatic considerations.
2004 Jan
Pentazocine-induced cutaneous sclerosis and panniculitis in an Indian male.
2004 Jul
Involvement of P-glycoprotein in blood-brain barrier transport of pentazocine in rats using brain uptake index method.
2004 Jun
Sigma-2 receptors are specifically localized to lipid rafts in rat liver membranes.
2004 Jun 16
Sternoclavicular septic arthritis: review of 180 cases.
2004 May
Experimental pain models reveal no sex differences in pentazocine analgesia in humans.
2004 May
Intrathecal morphine, but not buprenorphine or pentazocine, can induce spastic paraparesis after a noninjurious interval of spinal cord ischemia in the rat.
2004 Nov
Modulation of bradykinin-induced calcium changes in SH-SY5Y cells by neurosteroids and sigma receptor ligands via a shared mechanism.
2004 Nov
[Case report of pentazocine dependence from a standpoint of the cognitive therapy].
2004 Oct
Retroperitoneoscopic live donor nephrectomy: extended experience in a single center.
2004 Sep
Vitamin B12-associated localized scleroderma and its treatment.
2004 Sep
Sex-related psychological predictors of baseline pain perception and analgesic responses to pentazocine.
2005 Apr
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 HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN  
Official Name English
PENTAZOCINE HYDROCHLORIDE [VANDF]
Common Name English
PENTAZOCINE HYDROCHLORIDE [MI]
Common Name English
PENTAZOCINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
PENTAZOCINE HYDROCHLORIDE COMPONENT OF TALWIN COMPOUND
Common Name English
PENTAZOCINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
TALACEN COMPONENT PENTAZOCINE HYDROCHLORIDE
Common Name English
PENTAZOCINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
TALWIN NX COMPONENT PENTAZOCINE HYDROCHLORIDE
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)-, HYDROCHLORIDE, (2.ALPHA.,6.ALPHA.,11R*)-
Common Name English
PENTAZOCINE HYDROCHLORIDE COMPONENT OF TALWIN NX
Common Name English
TALWIN 50
Brand Name English
PENTAZOCINE HYDROCHLORIDE [USAN]
Common Name English
PENTAZOCINE HYDROCHLORIDE COMPONENT OF TALACEN
Common Name English
PENTAZOCINE HYDROCHLORIDE [MART.]
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 HYDROCHLORIDE
Common Name English
TALWIN COMPOUND COMPONENT PENTAZOCINE HYDROCHLORIDE
Common Name English
PENTAZOCINE HCL
Common Name English
Pentazocine hydrochloride [WHO-DD]
Common Name English
PENTAZOCINE HYDROCHLORIDE [JAN]
Common Name English
Classification Tree Code System Code
DEA NO. 9709
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
Code System Code Type Description
EVMPD
SUB03685MIG
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
PRIMARY
RXCUI
104973
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
PRIMARY RxNorm
CAS
2276-52-0
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
ECHA (EC/EINECS)
218-896-9
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
ALTERNATIVE
PUBCHEM
441277
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
PRIMARY
SMS_ID
100000085525
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
PRIMARY
FDA UNII
A36BXO4PPX
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
PRIMARY
MERCK INDEX
m8503
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C47661
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
PRIMARY
DAILYMED
A36BXO4PPX
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID00915701
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
PRIMARY
CAS
64024-15-3
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
PRIMARY
DRUG BANK
DBSALT001009
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
PRIMARY
ECHA (EC/EINECS)
264-612-1
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
PRIMARY
ChEMBL
CHEMBL560
Created by admin on Fri Dec 15 16:00:06 GMT 2023 , Edited by admin on Fri Dec 15 16:00:06 GMT 2023
PRIMARY