PENTAZOCINE, (-)-

Details

Stereochemistry	ABSOLUTE
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 221 Target ID: CHEMBL233 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2831363	Antagonist 2737		6.9 nM [Ki]
Kappa opioid receptor 108 Target ID: CHEMBL237 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2831363	Agonist 2637		75.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 607 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/016194s079s080lbl.pdf	Primary		Approved 8307	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 1670			inhibitor 1570

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Nav1.5 95	CYP1A2 1013 P-gp 1491

Drug as victim

Target	Modality	Activity
CYP1A2 1013	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17823102/ Page: 6.0	likely
CYP3A4 1670	substrate 3264 Sources: https://pubmed.ncbi.nlm.nih.gov/17823102/ Page: 6.0	likely
P-gp 1491	substrate 3264 Sources: https://europepmc.org/article/med/24915880#R34	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Nav1.5 98	inhibitor 1584 Sources: https://pubmed.ncbi.nlm.nih.gov/19279232/ Page: 3.0
hERG 1603	inhibitor 1584 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
Pentazocine addict nephropathy: a case report.	1992 Mar	1316215
WHO Expert Committee on Drug Dependence. Thirty-second report.	2001	11851193
The opioid peptide analogue biphalin induces less physical dependence than morphine.	2001 Jul 20	11508644
[Analysis of prehospital analgesia administered to victims with traumatic injuries].	2001 Jul-Aug	11586642
Post operative pain therapy: a survey of prescribing patterns and adequacy of analgesia in Ibadan, Nigeria.	2001 Mar	11961861
[UV-densitometry determination of pentazocine hydrochloride in tablets after low temperature extraction].	2001 May-Jun	11548553
Modulation of serotonergic neurotransmission by short- and long-term treatments with sigma ligands.	2001 Oct	11588125
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
[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
Renal amyloidosis in a pentazocine addict.	2002 Jul	12126358
Fibromyositis after intramuscular pentazocine abuse.	2002 Jul-Sep	12432208
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
Effects of histamine and opioid systems on memory retention of passive avoidance learning in rats.	2002 Oct 4	12354569
Subarachnoid block for lower abdominal and lower limb surgery: UITH experience.	2002 Oct-Dec	12955990
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
Permanently oriented antibody immobilization for digoxin determination with a flow-through fluoroimmunosensor.	2003 Apr	12733013
Efficacy of intrathecal morphine for analgesia following elective cesarean section: comparison with previous delivery.	2003 Aug	12928713
Postoperative pain management following caesarean section in University of Ilorin Teaching Hospital (UITH), Ilorin, Nigeria.	2003 Dec	15008293
Enhanced sensitivity to the antinociceptive effects of kappa opioids in naltrexone-treated rats: dose- and time-dependent effects.	2003 Dec	14665981
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
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
Analgesic activity of Piper longum Linn. root.	2003 Jun	15266916
Role of kappa-opioid receptor activation in pharmacological preconditioning of swine.	2003 Jun	12543635
The analgesic effect of oral morphine or pentazocine for extracorporeal shock wave lithotripsy.	2003 Mar	12747344
[Neurochemical analysis and pharmacological regulation of the corticofugal control of the nociceptive signals in the afferent pathways].	2003 Mar-Apr	12962044
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
Procaine hydrochloride fails to relieve pain in patients with acute pancreatitis.	2004	14755147
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
Antiproliferative and cytotoxic effects of some sigma2 agonists and sigma1 antagonists in tumour cell lines.	2004 Aug	15322732
Delta-opioid receptor agonist reduces severity of postresuscitation myocardial dysfunction.	2004 Aug	15044199
[Intermittent complete left bundle branch block during general anesthesia].	2004 Dec	15682804
Pentazocine-induced cutaneous sclerosis and panniculitis in an Indian male.	2004 Jul	15230891
Involvement of P-glycoprotein in blood-brain barrier transport of pentazocine in rats using brain uptake index method.	2004 Jun	15187451
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
[Case report of pentazocine dependence from a standpoint of the cognitive therapy].	2004 Oct	15573677
Retroperitoneoscopic live donor nephrectomy: extended experience in a single center.	2004 Sep	15518698
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 `Fri Dec 16 16:10:38 UTC 2022` Edited by `admin` on `Fri Dec 16 16:10:38 UTC 2022`
Record UNII	768DQ5A5AI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PENTAZOCINE, (-)-

Common Name

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)-

Systematic Name

English

LEVOPENTAZOCINE

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)-, CIS-(-)-

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)-, (2R,6R,11R)-

Common Name

English

PENTAZOCINE, L-

Common Name

English

PENTAZOCINE 2R,6R,11R-FORM

Common Name

English

PENTAZOCINE 2R,6R,11R-FORM [MI]

Common Name

English

CIS-(-)-PENTAZOCINE

Common Name

English

(2R,6R,11R)-1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(3-METHYL-2-BUTEN-1-YL)-2,6-METHANO-3-BENZAZOCIN-8-OL

Common Name

English

(-)-.ALPHA.-PENTAZOCINE

Common Name

English

L-PENTAZOCINE

Common Name

English

(-)-PENTAZOCINE

Common Name

English

Code System Code Type Description

CAS

10279-67-1