PENTAZOCINE HYDROCHLORIDE

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 Search

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

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

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2831363	Antagonist 2760		6.9 nM [Ki]
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2831363	Agonist 2662		75.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 608 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/016194s079s080lbl.pdf	Primary		Approved 8360	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

C_max

Value	Dose	Co-administered	Analyte	Population
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
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

AUC

Value	Dose	Co-administered	Analyte	Population
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
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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
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

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 Co-administed with:: benzodiazepines 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 Co-administed with:: benzodiazepines 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 Co-administed with:: benzodiazepines 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 1709			inhibitor 1599

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 95	CYP1A2 1032 P-gp 1527

Drug as victim

Target	Modality	Activity
CYP1A2 1032	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/17823102/ Page: 6.0	likely
CYP3A4 1709	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/17823102/ Page: 6.0	likely
P-gp 1527	substrate 3326 Sources: https://europepmc.org/article/med/24915880#R34	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 98	inhibitor 1613 Sources: https://pubmed.ncbi.nlm.nih.gov/19279232/ Page: 3.0
hERG 1632	inhibitor 1613 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
THE BioTek	bt-278515	https://www.thebiotek.com/product/inhibitors/bt-278515
THE BioTek	bt-278516	https://www.thebiotek.com/product/inhibitors/bt-278516
Tetrahedron	TS54857
Yick-Vic Chemicals & Pharmaceuticals (HK) Ltd.	PH-0691A
ZINC	ZINC000000000596	http://zinc15.docking.org/substances/ZINC000000000596

PubMed

Title	Date	PubMed
Clinical effects of pentazocine in hospitalized medical patients.	1975 Feb-Mar	1123460
Pentazocine-induced fibrous myopathy.	1975 Jan 20	1172732
Letter: Pentazocine-induced fibrous myopathy.	1975 Jun 16	1173609
WHO Expert Committee on Drug Dependence. Thirty-second report.	2001	11851193
Anti-inflammatory and analgesic activity of Indian Hypericum perforatum L.	2001 Apr	11491578
Effects of AH-9700, (+)-pentazocine, DTG and oxybutynin on micturition in anesthetized rats with acetone-induced cystitis.	2001 Aug 24	11589509
Subjective, psychomotor, and physiological effects of cumulative doses of mixed-action opioids in healthy volunteers.	2001 Jun	11441425
TRK-820, a selective kappa-opioid agonist, produces potent antinociception in cynomolgus monkeys.	2001 Mar	11325021
A multireceptorial binding reinvestigation on an extended class of sigma ligands: N-[omega-(indan-1-yl and tetralin-1-yl)alkyl] derivatives of 3,3-dimethylpiperidine reveal high affinities towards sigma1 and EBP sites.	2001 May	11377189
Experience with urine drug testing by the Correctional Service of Canada.	2001 Sep 15	11516882
[Biopharmaceutical studies on molecular mechanisms of membrane transport].	2002 Dec	12510384
Pharmacological treatment of postoperative shivering: a quantitative systematic review of randomized controlled trials.	2002 Feb	11812718
Substance abuse monitoring by the Correctional Service of Canada.	2002 Feb	11805743
Binding of sigma receptor ligands and their effects on muscarine-induced Ca(2+) changes in SH-SY5Y cells.	2002 Feb 1	11834244
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	12036376
Sigma1 receptor modulation of opioid analgesia in the mouse.	2002 Mar	11861817
Synthesis and evaluation of [18F]fluoroethyl SA4503 as a PET ligand for the sigma receptor.	2002 Mar 15	11835521
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	12031882
[Perioperative management for nephrectomy using combined spinal-epidural anesthesia with sedation in a patient with cerebral palsy under maintenance hemodialysis].	2002 Nov	12481458
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	14557376
Age-related changes of the binding of [3h]SA4503 to sigma1 receptors in the rat brain.	2003 Feb	12691135
Gabapentin in the management of pentazocine dependence: a potent analgesic--anticraving agent.	2003 Jul	14621035
[Neurochemical analysis and pharmacological regulation of the corticofugal control of the nociceptive signals in the afferent pathways].	2003 Mar-Apr	12962044
Opioid agonists have different efficacy profiles for G protein activation, rapid desensitization, and endocytosis of mu-opioid receptors.	2003 May 23	12642578
Dose ratio is important in maximizing naloxone enhancement of nalbuphine analgesia in humans.	2003 Nov 6	14550900
Generation and phenotypic analysis of sigma receptor type I (sigma 1) knockout mice.	2003 Oct	14622179
[Combined use of intrathecal morphine and diclofenac suppository for postoperative analgesia after caesarean section].	2003 Oct	14598667
Effect of insulin hypoglycemic stress on nociceptive responses to mu- and kappa-opioid receptor agonists at LH-surge in female rats.	2004 Apr	15148524
The sigma receptor ligand (+)-pentazocine prevents apoptotic retinal ganglion cell death induced in vitro by homocysteine and glutamate.	2004 Apr 7	15046867
Molecular modeling of sigma 1 receptor ligands: a model of binding conformational and electrostatic considerations.	2004 Jan	14629980
Involvement of P-glycoprotein in blood-brain barrier transport of pentazocine in rats using brain uptake index method.	2004 Jun	15187451
Sigma-2 receptors are specifically localized to lipid rafts in rat liver membranes.	2004 Jun 16	15189760
Sternoclavicular septic arthritis: review of 180 cases.	2004 May	15118542
Experimental pain models reveal no sex differences in pentazocine analgesia in humans.	2004 May	15114226
Sex-related psychological predictors of baseline pain perception and analgesic responses to pentazocine.	2005 Apr	15740828
Using mixed agonist-antagonists.	2005 Feb	15706252

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 `Wed Jul 05 23:28:16 UTC 2023` Edited by `admin` on `Wed Jul 05 23:28:16 UTC 2023`
Record UNII	A36BXO4PPX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PENTAZOCINE HYDROCHLORIDE

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