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

Details

Stereochemistry RACEMIC
Molecular Formula C19H27NO
Molecular Weight 285.4238
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENTAZOCINE

SMILES

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

Molecular Formula C19H27NO
Molecular Weight 285.4238
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

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
Pentazocine-induced fibrous myopathy.
1975 Jan 20
Iatrogenic muscle fibrosis. Arm levitation as an initial sign.
1975 Nov 10
WHO Expert Committee on Drug Dependence. Thirty-second report.
2001
Effects of AH-9700, (+)-pentazocine, DTG and oxybutynin on micturition in anesthetized rats with acetone-induced cystitis.
2001 Aug 24
Multiple pathways of sigma(1) receptor ligand uptakes into primary cultured neuronal cells.
2001 Aug 3
[Opioid tolerance and dependence--pharmacological aspects].
2001 Jul-Sep
Post operative pain therapy: a survey of prescribing patterns and adequacy of analgesia in Ibadan, Nigeria.
2001 Mar
[UV-densitometry determination of pentazocine hydrochloride in tablets after low temperature extraction].
2001 May-Jun
Modulation of serotonergic neurotransmission by short- and long-term treatments with sigma ligands.
2001 Oct
Oxygen saturation in healthy newborn infants immediately after birth measured by pulse oximetry.
2002 Apr
Evidence for sigma-1-like receptors in isolated rat liver mitochondrial membranes.
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
[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
[Sedation analgesia in interventional radiology].
2002 Feb
Substance abuse monitoring by the Correctional Service of Canada.
2002 Feb
Renal amyloidosis in a pentazocine addict.
2002 Jul
Sigma receptors inhibit high-voltage-activated calcium channels in rat sympathetic and parasympathetic neurons.
2002 Jun
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
Effects of adding midazolam on the postoperative epidural analgesia with two different doses of bupivacaine.
2002 Mar
Sigma1 receptor modulation of opioid analgesia in the mouse.
2002 Mar
Synthesis and evaluation of 3-(4-chlorobenzyl)-8-[11C]methoxy-1,2,3,4-tetrahydrochromeno[3,4-c]pyridin-5-one: a PET tracer for imaging sigma(1) receptors.
2002 May
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
Effects of histamine and opioid systems on memory retention of passive avoidance learning in rats.
2002 Oct 4
Subarachnoid block for lower abdominal and lower limb surgery: UITH experience.
2002 Oct-Dec
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
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
Sigma1 receptor agonist-mediated regulation of N-methyl-D-aspartate-stimulated [3H]dopamine release is dependent upon protein kinase C.
2003 Jan
Opioid prescription for terminally ill outpatients in a district of northern Italy: a retrospective survey.
2003 Jul
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
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
[Combined use of intrathecal morphine and diclofenac suppository for postoperative analgesia after caesarean section].
2003 Oct
The sigma receptor ligand (+)-pentazocine prevents apoptotic retinal ganglion cell death induced in vitro by homocysteine and glutamate.
2004 Apr 7
[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
Sigma-2 receptors are specifically localized to lipid rafts in rat liver membranes.
2004 Jun 16
Experimental pain models reveal no sex differences in pentazocine analgesia in humans.
2004 May
Retroperitoneoscopic live donor nephrectomy: extended experience in a single center.
2004 Sep
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.
Substance Class Chemical
Created
by admin
on Fri Dec 16 16:20:16 UTC 2022
Edited
by admin
on Fri Dec 16 16:20:16 UTC 2022
Record UNII
RP4A60D26L
Record Status Validated (UNII)
Record Version
  • Download
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 IMPURITY]
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
Pentazocine [WHO-DD]
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 [EP MONOGRAPH]
Common Name English
PENTAZOCINE [USAN]
Common Name English
PENTAZOCINE [MI]
Common Name English
PENTAZOCINE [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
WHO-VATC QN02AD01
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
LIVERTOX NBK548498
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
NDF-RT N0000175686
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
WHO-ATC N02AD01
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
DEA NO. 9709
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
NDF-RT N0000175685
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
NCI_THESAURUS C1506
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
NDF-RT N0000175688
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
Code System Code Type Description
DRUG CENTRAL
3424
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
MESH
D010423
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
HSDB
3150
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
MERCK INDEX
M8503
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY Merck Index
WIKIPEDIA
PENTAZOCINE
Created by admin on Fri Dec 16 16:20:17 UTC 2022 , Edited by admin on Fri Dec 16 16:20:17 UTC 2022
PRIMARY
DRUG BANK
DB00652
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
FDA UNII
RP4A60D26L
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
EVMPD
SUB09688MIG
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
ChEMBL
CHEMBL560
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
RS_ITEM_NUM
1505007
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
CAS
359-83-1
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
DAILYMED
RP4A60D26L
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
LACTMED
Pentazocine
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
INN
1674
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
NCI_THESAURUS
C61884
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
RXCUI
8001
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY RxNorm
NSC
107430
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
ECHA (EC/EINECS)
206-634-6
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
EPA CompTox
DTXSID7023433
Created by admin on Fri Dec 16 16:20:16 UTC 2022 , Edited by admin on Fri Dec 16 16:20:16 UTC 2022
PRIMARY
Related Record Type Details
ENANTIOMER -> RACEMATE
TARGET -> AGONIST
(+)-pentazocine is active
ENANTIOMER -> RACEMATE
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
USP
SALT/SOLVATE -> PARENT
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY