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
Letter: Pentazocine-induced fibrous myopathy.
1975 Jun 16
Effect of drugs influencing central serotonergic mechanisms on pentazocine-induced catalepsy in mice.
1998 Dec
Pentazocine-induced fibromyositis and contracture.
1999 Jun
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
Pharmacological actions of AH-9700 on micturition reflex in anesthetized rats.
2001 Jan 26
[Opioid tolerance and dependence--pharmacological aspects].
2001 Jul-Sep
TRK-820, a selective kappa-opioid agonist, produces potent antinociception in cynomolgus monkeys.
2001 Mar
[Influence of intubation maneuver with or without premedication for intracranial hemorrhage with unconsciousness].
2001 Mar
Some of the effects of the selective sigma ligand (+)pentazocine are mediated via a naloxone-sensitive receptor.
2001 Mar 15
Potentiation of opioid analgesia in dopamine2 receptor knock-out mice: evidence for a tonically active anti-opioid system.
2001 Oct 1
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
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
Sigma1 receptor modulation of opioid analgesia in the mouse.
2002 Mar
Synthesis and evaluation of [18F]fluoroethyl SA4503 as a PET ligand for the sigma receptor.
2002 Mar 15
[Perioperative management for nephrectomy using combined spinal-epidural anesthesia with sedation in a patient with cerebral palsy under maintenance hemodialysis].
2002 Nov
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
Cardiovascular effects of intravenous pentazocine and cyclazocine in conscious, curarized-conscious, and anesthetized dogs.
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
Enhanced sensitivity to the antinociceptive effects of kappa opioids in naltrexone-treated rats: dose- and time-dependent effects.
2003 Dec
Effects of ethanol or rimcazole on dizocilpine maleate-induced behaviors in male and female rats.
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
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
[Combined use of intrathecal morphine and diclofenac suppository for postoperative analgesia after caesarean section].
2003 Oct
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
Molecular modeling of sigma 1 receptor ligands: a model of binding conformational and electrostatic considerations.
2004 Jan
Involvement of P-glycoprotein in blood-brain barrier transport of pentazocine in rats using brain uptake index method.
2004 Jun
Sternoclavicular septic arthritis: review of 180 cases.
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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:41:02 UTC 2023
Edited
by admin
on Wed Jul 05 22:41:02 UTC 2023
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 Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
WHO-VATC QN02AD01
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
LIVERTOX NBK548498
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
NDF-RT N0000175686
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
WHO-ATC N02AD01
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
DEA NO. 9709
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
NDF-RT N0000175685
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
NCI_THESAURUS C1506
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
NDF-RT N0000175688
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
Code System Code Type Description
DRUG CENTRAL
3424
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
SMS_ID
100000082491
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
MESH
D010423
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
HSDB
3150
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
MERCK INDEX
M8503
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
PENTAZOCINE
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
DRUG BANK
DB00652
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
FDA UNII
RP4A60D26L
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
EVMPD
SUB09688MIG
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
ChEMBL
CHEMBL560
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
RS_ITEM_NUM
1505007
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
CAS
359-83-1
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
DAILYMED
RP4A60D26L
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
LACTMED
Pentazocine
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
INN
1674
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
NCI_THESAURUS
C61884
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
RXCUI
8001
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY RxNorm
NSC
107430
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-634-6
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
PRIMARY
EPA CompTox
DTXSID7023433
Created by admin on Wed Jul 05 22:41:02 UTC 2023 , Edited by admin on Wed Jul 05 22:41:02 UTC 2023
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