PENTAZOCINE

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 Search

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
Sources: https://www.drugs.com/cdi/pentazocine.html | https://www.ncbi.nlm.nih.gov/pubmed/23370666
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 231 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2831363	Antagonist 2849		6.9 nM [Ki]
Kappa opioid receptor 115 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2831363	Agonist 2752		75.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/016194s079s080lbl.pdf	Primary		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
102 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032/	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

Value	Dose	Co-administered	Analyte	Population
536 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032/	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3709032/	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

Dose	Population	Adverse events
30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	Disc. AE: Respiratory depression, Hypotension... AEs leading to discontinuation/dose reduction: Respiratory depression Hypotension (severe) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf
30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	Disc. AE: Sedation, Coma... AEs leading to discontinuation/dose reduction: Sedation Coma Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf

AEs

AE	Significance	Dose	Population
Respiratory depression	Disc. AE	30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf
Hypotension	severe Disc. AE	30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf
Coma	Disc. AE	30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf
Sedation	Disc. AE	30 mg single, intramuscular Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/016194s081lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946			inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 116	CYP1A2 1197 P-gp 2052

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17823102/ Page: 6.0	likely
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/17823102/ Page: 6.0	likely
P-gp 2052	substrate 4014 Sources: https://europepmc.org/article/med/24915880#R34	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 119	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/19279232/ Page: 3.0
hERG 2263	inhibitor 2237 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3151040/

Sourcing

Vendor/Aggregator	ID	URL
Chemieliva Pharmaceutical Co., Ltd	PBCM1405771
Compound Cloud	441277
Compound Cloud	441278
Compound Cloud	656697
Finetech	FT-0673607	http://www.finetechnology-ind.com/product/All%20product%20List/7488-49-5.html
MuseChem	I011222	https://www.musechem.com/product/I011222.html
NovoSeek	441278
Smolecule	S538980	http://www.smolecule.com/products/s538980
Smolecule	S538981	http://www.smolecule.com/products/s538981
Tetrahedron	TS54857
THE BioTek	bt-278515	https://www.thebiotek.com/product/inhibitors/bt-278515
THE BioTek	bt-278516	https://www.thebiotek.com/product/inhibitors/bt-278516
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0691A
ZINC	ZINC000000000596	http://zinc15.docking.org/substances/ZINC000000000596

PubMed

Title	Date	PubMed
Sex-related psychological predictors of baseline pain perception and analgesic responses to pentazocine.	2005-04	15740828
Using mixed agonist-antagonists.	2005-02	15706252
[Intermittent complete left bundle branch block during general anesthesia].	2004-12	15682804
Intrathecal morphine, but not buprenorphine or pentazocine, can induce spastic paraparesis after a noninjurious interval of spinal cord ischemia in the rat.	2004-11	15502059
Modulation of bradykinin-induced calcium changes in SH-SY5Y cells by neurosteroids and sigma receptor ligands via a shared mechanism.	2004-11	15352135
[Case report of pentazocine dependence from a standpoint of the cognitive therapy].	2004-10	15573677
Retroperitoneoscopic live donor nephrectomy: extended experience in a single center.	2004-09	15518698
Vitamin B12-associated localized scleroderma and its treatment.	2004-09	15355372
Antiproliferative and cytotoxic effects of some sigma2 agonists and sigma1 antagonists in tumour cell lines.	2004-08	15322732
Delta-opioid receptor agonist reduces severity of postresuscitation myocardial dysfunction.	2004-08	15044199
Pentazocine-induced cutaneous sclerosis and panniculitis in an Indian male.	2004-07	15230891
Sigma-2 receptors are specifically localized to lipid rafts in rat liver membranes.	2004-06-16	15189760
Involvement of P-glycoprotein in blood-brain barrier transport of pentazocine in rats using brain uptake index method.	2004-06	15187451
Sternoclavicular septic arthritis: review of 180 cases.	2004-05	15118542
Experimental pain models reveal no sex differences in pentazocine analgesia in humans.	2004-05	15114226
The sigma receptor ligand (+)-pentazocine prevents apoptotic retinal ganglion cell death induced in vitro by homocysteine and glutamate.	2004-04-07	15046867
Effect of insulin hypoglycemic stress on nociceptive responses to mu- and kappa-opioid receptor agonists at LH-surge in female rats.	2004-04	15148524
Molecular modeling of sigma 1 receptor ligands: a model of binding conformational and electrostatic considerations.	2004-01	14629980
Procaine hydrochloride fails to relieve pain in patients with acute pancreatitis.	2004	14755147
Postoperative pain management following caesarean section in University of Ilorin Teaching Hospital (UITH), Ilorin, Nigeria.	2003-12	15008293
Enhanced sensitivity to the antinociceptive effects of kappa opioids in naltrexone-treated rats: dose- and time-dependent effects.	2003-12	14665981
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.	2003-12	14557376
Dose ratio is important in maximizing naloxone enhancement of nalbuphine analgesia in humans.	2003-11-06	14550900
Modulation of Fas receptor proteins and dynamin during opiate addiction and induction of opiate withdrawal in rat brain.	2003-11	14530904
Generation and phenotypic analysis of sigma receptor type I (sigma 1) knockout mice.	2003-10	14622179
[Combined use of intrathecal morphine and diclofenac suppository for postoperative analgesia after caesarean section].	2003-10	14598667
[Neurochemical analysis and pharmacological regulation of the corticofugal control of the nociceptive signals in the afferent pathways].	2003-09-10	12962044
Subarachnoid block for lower abdominal and lower limb surgery: UITH experience.	2003-09-06	12955990
Efficacy of intrathecal morphine for analgesia following elective cesarean section: comparison with previous delivery.	2003-08	12928713
Intracellular dynamics of sigma-1 receptors (sigma(1) binding sites) in NG108-15 cells.	2003-08	12730356
Migratory hydroamination: a facile enantioselective synthesis of benzomorphans.	2003-07-23	12862467
Gabapentin in the management of pentazocine dependence: a potent analgesic--anticraving agent.	2003-07	14621035
Opioid prescription for terminally ill outpatients in a district of northern Italy: a retrospective survey.	2003-07	12770518
Analgesic activity of Piper longum Linn. root.	2003-06	15266916
Role of kappa-opioid receptor activation in pharmacological preconditioning of swine.	2003-06	12543635
Opioid agonists have different efficacy profiles for G protein activation, rapid desensitization, and endocytosis of mu-opioid receptors.	2003-05-23	12642578
Different brain kinetics of two sigma 1 receptor ligands, [3H](+)-pentazocine and [11C]SA4503, by P-glycoprotein modulation.	2003-05	12619041
Agonist/antagonist properties of nalbuphine, butorphanol and (-)-pentazocine in male vs. female rats.	2003-04	12759132
Permanently oriented antibody immobilization for digoxin determination with a flow-through fluoroimmunosensor.	2003-04	12733013
The analgesic effect of oral morphine or pentazocine for extracorporeal shock wave lithotripsy.	2003-03	12747344
SR31747A is a sigma receptor ligand exhibiting antitumoural activity both in vitro and in vivo.	2003-02-10	12569389
Effects of ethanol or rimcazole on dizocilpine maleate-induced behaviors in male and female rats.	2003-02	12782248
Age-related changes of the binding of [3h]SA4503 to sigma1 receptors in the rat brain.	2003-02	12691135
Sex differences in (-)-pentazocine antinociception: comparison to morphine and spiradoline in four rat strains using a thermal nociceptive assay.	2003-02	12576884
Cardiovascular effects of intravenous pentazocine and cyclazocine in conscious, curarized-conscious, and anesthetized dogs.	2003	14964736
Demographics, assessment and management of pain in the elderly.	2003	12513114
[The effect of ketamine on reducing postoperative agitation after sevoflurane anesthesia in pediatric strabismus surgery].	2002-12	12607270
[Biopharmaceutical studies on molecular mechanisms of membrane transport].	2002-12	12510384
Pentazocine addict nephropathy: a case report.	1992-03	1316215
Iatrogenic muscle fibrosis. Arm levitation as an initial sign.	1975-11-10	126328

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

In Vitro Use Guide

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 `Mon Mar 31 17:48:17 GMT 2025` Edited by `admin` on `Mon Mar 31 17:48:17 GMT 2025`
Record UNII	RP4A60D26L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PENTAZOCINE

Official Name

English

PENTAZOCINE CIV

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