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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

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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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
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
Sources:
unhealthy
Sedation Disc. AE
30 mg single, intramuscular
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
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
Anti-inflammatory and analgesic activity of Indian Hypericum perforatum L.
2001 Apr
Molecular cloning and pharmacological characterization of the rat sigma1 receptor.
2001 Aug 1
Effects of AH-9700, (+)-pentazocine, DTG and oxybutynin on micturition in anesthetized rats with acetone-induced cystitis.
2001 Aug 24
Post operative pain therapy: a survey of prescribing patterns and adequacy of analgesia in Ibadan, Nigeria.
2001 Mar
[Influence of intubation maneuver with or without premedication for intracranial hemorrhage with unconsciousness].
2001 Mar
Chitosan based pentazocine microspheres for intranasal systemic delivery: development and biopharmaceutical evaluation.
2001 Mar
Modulation of serotonergic neurotransmission by short- and long-term treatments with sigma ligands.
2001 Oct
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
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
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
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
Efficacy of intrathecal morphine for analgesia following elective cesarean section: comparison with previous delivery.
2003 Aug
Sigma1 receptor agonist-mediated regulation of N-methyl-D-aspartate-stimulated [3H]dopamine release is dependent upon protein kinase C.
2003 Jan
Analgesic activity of Piper longum Linn. root.
2003 Jun
Role of kappa-opioid receptor activation in pharmacological preconditioning of swine.
2003 Jun
Antiproliferative and cytotoxic effects of some sigma2 agonists and sigma1 antagonists in tumour cell lines.
2004 Aug
[Intermittent complete left bundle branch block during general anesthesia].
2004 Dec
Pentazocine-induced cutaneous sclerosis and panniculitis in an Indian male.
2004 Jul
[Case report of pentazocine dependence from a standpoint of the cognitive therapy].
2004 Oct
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
EP   HSDB   INN   MART.   MI   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
PENTAZOCINE CIV
USP-RS  
Preferred 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
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 Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
WHO-VATC QN02AD01
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LIVERTOX NBK548498
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NDF-RT N0000175686
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WHO-ATC N02AD01
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DEA NO. 9709
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NDF-RT N0000175685
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NCI_THESAURUS C1506
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NDF-RT N0000175688
Created by admin on Mon Mar 31 17:48:17 GMT 2025 , Edited by admin on Mon Mar 31 17:48:17 GMT 2025
Code System Code Type Description
DRUG CENTRAL
3424
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PRIMARY
SMS_ID
100000082491
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PRIMARY
MESH
D010423
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PRIMARY
HSDB
3150
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PRIMARY
MERCK INDEX
m8503
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PRIMARY Merck Index
WIKIPEDIA
PENTAZOCINE
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PRIMARY
DRUG BANK
DB00652
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PRIMARY
FDA UNII
RP4A60D26L
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PRIMARY
EVMPD
SUB09688MIG
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PRIMARY
ChEMBL
CHEMBL560
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PRIMARY
RS_ITEM_NUM
1505007
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PRIMARY
CAS
359-83-1
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PRIMARY
DAILYMED
RP4A60D26L
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PRIMARY
LACTMED
Pentazocine
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PRIMARY
INN
1674
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PRIMARY
NCI_THESAURUS
C61884
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PRIMARY
RXCUI
8001
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PRIMARY RxNorm
NSC
107430
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PRIMARY
ECHA (EC/EINECS)
206-634-6
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PRIMARY
EPA CompTox
DTXSID7023433
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PRIMARY