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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 of SURINABANT

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
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
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
Will the new CB1 cannabinoid receptor antagonist SR-147778 have advantages over rimonabant?
2005 Mar
WIN 55212-2 impairs contextual fear conditioning through the activation of CB1 cannabinoid receptors.
2006 Apr 10-17
SR147778, a CB1 cannabinoid receptor antagonist, suppresses ethanol preference in chronically alcoholized Wistar rats.
2006 Jul
The cannabinoid receptor agonist WIN 55,212-2 facilitates the extinction of contextual fear memory and spatial memory in rats.
2006 Nov
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
Effects of adolescent nicotine and SR 147778 (Surinabant) administration on food intake, somatic growth and metabolic parameters in rats.
2008 Jan
Critical role of the endocannabinoid system in the regulation of food intake and energy metabolism, with phylogenetic, developmental, and pathophysiological implications.
2008 Sep
Cannabinoid receptor antagonists: pharmacological opportunities, clinical experience, and translational prognosis.
2009 Mar
Patents

Patents

Sample Use Guides

5, 20 or 60 mg
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:12:35 GMT 2023
Edited
by admin
on Fri Dec 15 16:12:35 GMT 2023
Record UNII
SF8R9VCB0X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SURINABANT
INN  
INN  
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
Created by admin on Fri Dec 15 16:12:35 GMT 2023 , Edited by admin on Fri Dec 15 16:12:35 GMT 2023
Code System Code Type Description
DRUG BANK
DB13070
Created by admin on Fri Dec 15 16:12:35 GMT 2023 , Edited by admin on Fri Dec 15 16:12:35 GMT 2023
PRIMARY
SMS_ID
100000128132
Created by admin on Fri Dec 15 16:12:35 GMT 2023 , Edited by admin on Fri Dec 15 16:12:35 GMT 2023
PRIMARY
CAS
288104-79-0
Created by admin on Fri Dec 15 16:12:35 GMT 2023 , Edited by admin on Fri Dec 15 16:12:35 GMT 2023
PRIMARY
WIKIPEDIA
SURINABANT
Created by admin on Fri Dec 15 16:12:35 GMT 2023 , Edited by admin on Fri Dec 15 16:12:35 GMT 2023
PRIMARY
FDA UNII
SF8R9VCB0X
Created by admin on Fri Dec 15 16:12:35 GMT 2023 , Edited by admin on Fri Dec 15 16:12:35 GMT 2023
PRIMARY
EVMPD
SUB34885
Created by admin on Fri Dec 15 16:12:35 GMT 2023 , Edited by admin on Fri Dec 15 16:12:35 GMT 2023
PRIMARY
INN
8640
Created by admin on Fri Dec 15 16:12:35 GMT 2023 , Edited by admin on Fri Dec 15 16:12:35 GMT 2023
PRIMARY
PUBCHEM
9849616
Created by admin on Fri Dec 15 16:12:35 GMT 2023 , Edited by admin on Fri Dec 15 16:12:35 GMT 2023
PRIMARY
ChEMBL
CHEMBL189676
Created by admin on Fri Dec 15 16:12:35 GMT 2023 , Edited by admin on Fri Dec 15 16:12:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID2047357
Created by admin on Fri Dec 15 16:12:35 GMT 2023 , Edited by admin on Fri Dec 15 16:12:35 GMT 2023
PRIMARY
NCI_THESAURUS
C87598
Created by admin on Fri Dec 15 16:12:35 GMT 2023 , Edited by admin on Fri Dec 15 16:12:35 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY