SURINABANT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H23BrCl2N4O
Molecular Weight	522.265
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1=C(N(N=C1C(=O)NN2CCCCC2)C3=CC=C(Cl)C=C3Cl)C4=CC=C(Br)C=C4

InChI

InChIKey=HMXDWDSNPRNUKI-UHFFFAOYSA-N

InChI=1S/C23H23BrCl2N4O/c1-2-18-21(23(31)28-29-12-4-3-5-13-29)27-30(20-11-10-17(25)14-19(20)26)22(18)15-6-8-16(24)9-7-15/h6-11,14H,2-5,12-13H2,1H3,(H,28,31)

HIDE SMILES / InChI

Molecular Formula	C23H23BrCl2N4O
Molecular Weight	522.265
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/23278647 | https://www.ncbi.nlm.nih.gov/pubmed/22219220 | https://www.ncbi.nlm.nih.gov/pubmed/28666894

Surinabant is a cannabinoid receptor type 1 antagonist developed by Sanofi-Aventis for the treatment for nicotine addiction and obesity. In preclinical models, Surinabant reduced body weight gain, as well as plasma glucose levels and triglycerides. Surinabant also reduced insulin and leptin secretion and increased adiponectin and corticosterone levels in rats. Phase I and phase II studies showed good clinical safety profiles in healthy subjects and in obese subjects, although doses higher than 10mg/day were associated with gastrointestinal events and sleep disorders.

Originator

Approval Year

PubMed

Title	Date	PubMed
SR147778 [5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-ethyl-N-(1-piperidinyl)-1H-pyrazole-3-carboxamide], a new potent and selective antagonist of the CB1 cannabinoid receptor: biochemical and pharmacological characterization.	2004 Sep	15131245
Suppressing effect of the cannabinoid CB1 receptor antagonist, SR147778, on alcohol intake and motivational properties of alcohol in alcohol-preferring sP rats.	2005 Jan-Feb	15582988
Will the new CB1 cannabinoid receptor antagonist SR-147778 have advantages over rimonabant?	2005 Mar	15833065
WIN 55212-2 impairs contextual fear conditioning through the activation of CB1 cannabinoid receptors.	2006 Apr 10-17	16406322
SR147778, a CB1 cannabinoid receptor antagonist, suppresses ethanol preference in chronically alcoholized Wistar rats.	2006 Jul	17127132
The cannabinoid receptor agonist WIN 55,212-2 facilitates the extinction of contextual fear memory and spatial memory in rats.	2006 Nov	16947018
The role of the cannabinoid type 1 receptor and down-stream cAMP/DARPP-32 signal in the nucleus accumbens of methamphetamine-sensitized rats.	2007 Dec	17953657
Effects of adolescent nicotine and SR 147778 (Surinabant) administration on food intake, somatic growth and metabolic parameters in rats.	2008 Jan	17720206
Critical role of the endocannabinoid system in the regulation of food intake and energy metabolism, with phylogenetic, developmental, and pathophysiological implications.	2008 Sep	18782018
Cannabinoid receptor antagonists: pharmacological opportunities, clinical experience, and translational prognosis.	2009 Mar	19249987

Patents

Sample Use Guides

In Vivo Use Guide

5, 20 or 60 mg

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:12:35 UTC 2023` Edited by `admin` on `Fri Dec 15 16:12:35 UTC 2023`
Record UNII	SF8R9VCB0X
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

SURINABANT

Official Name

English

SR147778

Code

English

surinabant [INN]

Common Name

English

5-(4-BROMOPHENYL)-1-(2,4-DICHLOROPHENYL)-4-ETHYL-N-(PIPERIDIN-1-YL)-1H-PYRAZOLE-3-CARBOXAMIDE

Systematic Name

English

SR-147778

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C29728