PHENAZOCINE

US Previously Marketed

First approved in 1959

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H27NO
Molecular Weight	321.4559
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)CCN2CCC4=CC=CC=C4

InChI

InChIKey=ZQHYKVKNPWDQSL-KNXBSLHKSA-N

InChI=1S/C22H27NO/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/t16-,21+,22+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H27NO
Molecular Weight	321.4559
Charge	0
Count

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

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
Oral pentazocine and phenazocine: a comparison in postoperative pain.	1971 May	5556861
Phencyclidine impairs latent learning in mice: interaction between glutamatergic systems and sigma(1) receptors.	2001 Apr	11182540
The anti-amnesic effects of sigma1 (sigma1) receptor agonists confirmed by in vivo antisense strategy in the mouse.	2001 Apr 13	11292454
Differential involvement of the sigma(1) (sigma(1)) receptor in the anti-amnesic effect of neuroactive steroids, as demonstrated using an in vivo antisense strategy in the mouse.	2001 Dec	11739250
Involvement of the sigma receptor in passive-avoidance learning in the day-old chick during the second wave of neuronal activity.	2001 May	11300740
Modulation of dopamine uptake in rat nucleus accumbens: effect of specific dopamine receptor antagonists and sigma ligands.	2001 Oct 26	11602337
The antidepressant-like effect induced by sigma(1)-receptor agonists and neuroactive steroids in mice submitted to the forced swimming test.	2001 Sep	11504830
Receptor mechanisms and circuitry underlying NMDA antagonist neurotoxicity.	2002	11803444
The sigma receptor as a ligand-regulated auxiliary potassium channel subunit.	2002 Apr 25	11988171
MS-377, a selective sigma receptor ligand, indirectly blocks the action of PCP in the N-methyl-D-aspartate receptor ion-channel complex in primary cultured rat neuronal cells.	2002 Feb 22	11991251
Strain differences in sigma(1) receptor-mediated behaviours are related to neurosteroid levels.	2002 May	12028363
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
Activity of opioid ligands in cells expressing cloned mu opioid receptors.	2003 Jan 4	12513698
Anti-amnesic effect of dimemorfan in mice.	2003 Mar	12642396
Generation and phenotypic analysis of sigma receptor type I (sigma 1) knockout mice.	2003 Oct	14622179
Characterization of phenothiazine-induced apoptosis in neuroblastoma and glioma cell lines: clinical relevance and possible application for brain-derived tumors.	2004	14997012
Involvement of the sigma 1 receptor in the modulation of dopaminergic transmission by amantadine.	2004 Apr	15090047
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
Effects of (+)SKF 10047, a sigma-1 selective agonist, on isolation-induced aggression in male mice.	2006 Nov	17200725
Sigma-1 receptors bind cholesterol and remodel lipid rafts in breast cancer cell lines.	2007 Dec 1	18056441
sigma(2)-receptor ligand-mediated inhibition of inwardly rectifying K(+) channels in the heart.	2007 Jul	17460149
Involvement of the sigma1 receptor in inhibiting activity of fluvoxamine on marble-burying behavior: comparison with paroxetine.	2007 Jun 1	17349995
Inhibition of hyperpolarization-activated cation currents by phencyclidine and some sigma ligands in rat hippocampal CA1 pyramidal neurons in vitro.	2007 Sep	17631922
Combination of virtual screening and high throughput gene profiling for identification of novel liver X receptor modulators.	2008 Apr 10	18324758
sigma-1 receptors protect RGC-5 cells from apoptosis by regulating intracellular calcium, Bax levels, and caspase-3 activation.	2008 Jun	18296662
Sigma-1 receptor regulation of voltage-gated calcium channels involves a direct interaction.	2008 Nov	18641291
The C-terminal amidated analogue of the substance P (SP) fragment SP(1-7) attenuates the expression of naloxone-precipitated withdrawal in morphine dependent rats.	2009 Dec	19686790
Voltage-gated sodium channel modulation by sigma-receptors in cardiac myocytes and heterologous systems.	2009 May	19279232
Sigma1 receptor antagonists determine the behavioral pattern of the methamphetamine-induced stereotypy in mice.	2009 May	19052726

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:45:41 GMT 2023` Edited by `admin` on `Sat Dec 16 16:45:41 GMT 2023`
Record UNII	J0ND6N0AQC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENAZOCINE

Official Name

English

phenazocine [INN]

Common Name

English

Phenazocine [WHO-DD]

Common Name

English

PHENAZOCINE [MI]

Common Name

English

PHENETHYLAZOCINE

Common Name

English

(±)-.ALPHA.-PHENAZOCINE

Common Name

English

2,6-METHANO-3-BENZAZOCIN-8-OL, 1,2,3,4,5,6-HEXAHYDRO-6,11-DIMETHYL-3-(2-PHENYLETHYL)-

Systematic Name

English

PHENAZOCINE CIS-(±)-FORM [MI]

Common Name

English

PHENOBENZORPHAN

Common Name

English

IDS-NP-008

Code

English

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

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN02AD02