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	ClH
Molecular Weight	36.461
Charge	0
Count

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

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 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2831363	Antagonist 2778		6.9 nM [Ki]
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2831363	Agonist 2678		75.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/016194s079s080lbl.pdf	Primary		Approved 8429	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
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 1737			inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 97	CYP1A2 1054 P-gp 1537

Drug as victim

Target	Modality	Activity
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17823102/ Page: 6.0	likely
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/17823102/ Page: 6.0	likely
P-gp 1537	substrate 3367 Sources: https://europepmc.org/article/med/24915880#R34	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 100	inhibitor 1626 Sources: https://pubmed.ncbi.nlm.nih.gov/19279232/ Page: 3.0
hERG 1647	inhibitor 1626 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
Mental and emotional disturbance with pentazocine (Talwin) use.	1975 Jul	1154070
Iatrogenic muscle fibrosis. Arm levitation as an initial sign.	1975 Nov 10	126328
Pentazocine-induced fibromyositis and contracture.	1999 Jun	10435175
WHO Expert Committee on Drug Dependence. Thirty-second report.	2001	11851193
Phencyclidine impairs latent learning in mice: interaction between glutamatergic systems and sigma(1) receptors.	2001 Apr	11182540
Pharmacological actions of AH-9700 on micturition reflex in anesthetized rats.	2001 Jan 26	11165228
[Opioid tolerance and dependence--pharmacological aspects].	2001 Jul-Sep	12092171
Subjective, psychomotor, and physiological effects of cumulative doses of mixed-action opioids in healthy volunteers.	2001 Jun	11441425
Post operative pain therapy: a survey of prescribing patterns and adequacy of analgesia in Ibadan, Nigeria.	2001 Mar	11961861
Some of the effects of the selective sigma ligand (+)pentazocine are mediated via a naloxone-sensitive receptor.	2001 Mar 15	11169783
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
[UV-densitometry determination of pentazocine hydrochloride in tablets after low temperature extraction].	2001 May-Jun	11548553
Potentiation of opioid analgesia in dopamine2 receptor knock-out mice: evidence for a tonically active anti-opioid system.	2001 Oct 1	11567069
Experience with urine drug testing by the Correctional Service of Canada.	2001 Sep 15	11516882
[The effect of ketamine on reducing postoperative agitation after sevoflurane anesthesia in pediatric strabismus surgery].	2002 Dec	12607270
Pharmacological treatment of postoperative shivering: a quantitative systematic review of randomized controlled trials.	2002 Feb	11812718
Fibromyositis after intramuscular pentazocine abuse.	2002 Jul-Sep	12432208
Sigma receptors inhibit high-voltage-activated calcium channels in rat sympathetic and parasympathetic neurons.	2002 Jun	12037190
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
Investigation on the influx transport mechanism of pentazocine at the blood-brain barrier in rats using the carotid injection technique.	2002 Oct	12392093
Agonist/antagonist properties of nalbuphine, butorphanol and (-)-pentazocine in male vs. female rats.	2003 Apr	12759132
Permanently oriented antibody immobilization for digoxin determination with a flow-through fluoroimmunosensor.	2003 Apr	12733013
Intracellular dynamics of sigma-1 receptors (sigma(1) binding sites) in NG108-15 cells.	2003 Aug	12730356
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
Effects of ethanol or rimcazole on dizocilpine maleate-induced behaviors in male and female rats.	2003 Feb	12782248
Age-related changes of the binding of [3h]SA4503 to sigma1 receptors in the rat brain.	2003 Feb	12691135
Sex differences in (-)-pentazocine antinociception: comparison to morphine and spiradoline in four rat strains using a thermal nociceptive assay.	2003 Feb	12576884
Gabapentin in the management of pentazocine dependence: a potent analgesic--anticraving agent.	2003 Jul	14621035
Opioid prescription for terminally ill outpatients in a district of northern Italy: a retrospective survey.	2003 Jul	12770518
The analgesic effect of oral morphine or pentazocine for extracorporeal shock wave lithotripsy.	2003 Mar	12747344
Different brain kinetics of two sigma 1 receptor ligands, [3H](+)-pentazocine and [11C]SA4503, by P-glycoprotein modulation.	2003 May	12619041
Opioid agonists have different efficacy profiles for G protein activation, rapid desensitization, and endocytosis of mu-opioid receptors.	2003 May 23	12642578
Modulation of Fas receptor proteins and dynamin during opiate addiction and induction of opiate withdrawal in rat brain.	2003 Nov	14530904
Dose ratio is important in maximizing naloxone enhancement of nalbuphine analgesia in humans.	2003 Nov 6	14550900
Procaine hydrochloride fails to relieve pain in patients with acute pancreatitis.	2004	14755147
Antiproliferative and cytotoxic effects of some sigma2 agonists and sigma1 antagonists in tumour cell lines.	2004 Aug	15322732
Molecular modeling of sigma 1 receptor ligands: a model of binding conformational and electrostatic considerations.	2004 Jan	14629980
Sternoclavicular septic arthritis: review of 180 cases.	2004 May	15118542
Sex-related psychological predictors of baseline pain perception and analgesic responses to pentazocine.	2005 Apr	15740828

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 `Fri Dec 15 16:00:06 GMT 2023` Edited by `admin` on `Fri Dec 15 16:00:06 GMT 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