PHENAZOCINE HYDROBROMIDE

US Previously Marketed

First approved in 1959

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H27NO.BrH
Molecular Weight	402.368
Optical Activity	( + / - )
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Br.C[C@H]1[C@H]2CC3=CC=C(O)C=C3[C@]1(C)CCN2CCC4=CC=CC=C4

InChI

InChIKey=MNMGNPZLUMHSKK-BAONSNCKSA-N

InChI=1S/C22H27NO.BrH/c1-16-21-14-18-8-9-19(24)15-20(18)22(16,2)11-13-23(21)12-10-17-6-4-3-5-7-17;/h3-9,15-16,21,24H,10-14H2,1-2H3;1H/t16-,21+,22+;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C22H27NO
Molecular Weight	321.4559
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	BrH
Molecular Weight	80.912
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25972091 | https://www.ncbi.nlm.nih.gov/pubmed/10635445 | https://www.ncbi.nlm.nih.gov/pubmed/8148469

(-)-Phenazocine is an opioid analgesic drug, which is related to pentazocine and has a similar profile of effects. (-)-Phenazocine is a potent mu opioid receptor agonist. In addition, (−)-phenazocine is also known to bind to δ opioid receptors (DOR) and κ opioid receptors (KOR). Regarding their analgesic potency, (−)-phenazocine was twenty times more potent than morphine in the hot plate test and sixty times more potent than its dextro enantiomer when it was subcutaneously (s.c.) administered

Approval Year

Doses

Dose	Population	Adverse events
6 mg single, intramuscular Highest studied dose Dose: 6 mg Route: intramuscular Route: single Dose: 6 mg Sources: https://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.834.2450&rep=rep1&type=pdf Page: p.338	unhealthy Health Status: unhealthy Condition: Chronic pain due to cancer Sources: https://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.834.2450&rep=rep1&type=pdf Page: p.338	Sources: https://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.834.2450&rep=rep1&type=pdf Page: p.338

Sourcing

Vendor/Aggregator	ID	URL
Compound Cloud	443405
Toronto Research Chemicals	P295400
ZINC	ZINC000001481896	http://zinc15.docking.org/substances/ZINC000001481896

PubMed

Title	Date	PubMed
Involvement of the sigma receptor in passive-avoidance learning in the day-old chick during the second wave of neuronal activity.	2001 May	11300740
Antagonism of NMDA receptors by sigma receptor ligands attenuates chemical ischemia-induced neuronal death in vitro.	2002 Nov 29	12445574
Effects of sigma(1) receptor ligand MS-377 on D(2) antagonists-induced behaviors.	2002 Oct	12151023
Characterization of phenothiazine-induced apoptosis in neuroblastoma and glioma cell lines: clinical relevance and possible application for brain-derived tumors.	2004	14997012
Characterization of the non-competitive antagonist binding site of the NMDA receptor in dark Agouti rats.	2004 Aug 6	15240177
Enhanced antidepressant efficacy of sigma1 receptor agonists in rats after chronic intracerebroventricular infusion of beta-amyloid-(1-40) protein.	2004 Feb 20	14975704
Antitussive activity of sigma-1 receptor agonists in the guinea-pig.	2004 Jan	14691051
[Stimulation of the delta 1-receptors help to decrease reperfusion induced myocardial stunning].	2004 Mar-Apr	15131985
Dimemorfan enhances acetylcholine release from rat hippocampal slices.	2004 May 15	15081388
Age-related expression of sigma1 receptors and antidepressant efficacy of a selective agonist in the senescence-accelerated (SAM) mouse.	2005 Feb 15	15635598
Phenytoin differentially modulates the affinity of agonist and antagonist ligands for sigma 1 receptors of guinea pig brain.	2005 Mar 1	15635593
sigma(2)-receptor ligand-mediated inhibition of inwardly rectifying K(+) channels in the heart.	2007 Jul	17460149
sigma-1 receptors protect RGC-5 cells from apoptosis by regulating intracellular calcium, Bax levels, and caspase-3 activation.	2008 Jun	18296662
Voltage-gated sodium channel modulation by sigma-receptors in cardiac myocytes and heterologous systems.	2009 May	19279232

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:06:38 GMT 2023` Edited by `admin` on `Fri Dec 15 15:06:38 GMT 2023`
Record UNII	C1749020IH
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENAZOCINE HYDROBROMIDE

Common Name

English

2'-HYDROXY-5,9-DIMETHYL-2-PHENETHYL-6,7-BENZOMORPHAN, HYDROBROMIDE

Common Name

English

PHENETHYLAZOCINE BROMIDE

Systematic Name

English

PHENAZOCINE HYDROBROMIDE [MART.]

Common Name

English

NIH-7519

Code

English

PHENAZOCINE CIS-(±)-FORM HYDROBROMIDE

Common Name

English

2'-HYDROXY-5,9-DIMETHYL-2-PHENETHYL-6,7-BENZOMORPHAN, HBR

Common Name

English

PRINADOL

Common Name

English

NARPHEN

Brand Name

English

PHENAZOCINE HBR

Common Name

English

PHENAZOCINE CIS-(±)-FORM HYDROBROMIDE [MI]

Common Name

English

Phenazocine hydrobromide [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C67413