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CHEBI:34967 - rimonabant

ChEBI IDCHEBI:34967
ChEBI Namerimonabant
Stars
DefinitionA carbohydrazide obtained by formal condensation of the carboxy group of 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carboxylic acid with the amino group of 1-aminopiperidine. It is a potent and selective cannabinoid receptor 1 (CB1R) antagonist. Besides its antagonistic properties, numerous studies have shown that, at micromolar concentrations rimonabant behaves as an inverse agonist at CB1 receptors. The drug was the first selective CB1 antagonist/inverse agonist introduced into clinical practice to treat obesity and metabolic-related disorders. It was later withdrawn from market due to CNS-related adverse effects including depression and suicidal ideation.
Last Modified5 January 2021
DownloadsMolfile
FormulaC22H21Cl3N4O
Net Charge0
Average Mass463.796
Monoisotopic Mass462.07809
SMILESCc1c(C(=O)NN2CCCCC2)nn(-c2ccc(Cl)cc2Cl)c1-c1ccc(Cl)cc1
InChIInChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)
InChIKeyJZCPYUJPEARBJL-UHFFFAOYSA-N
Wikipedia
Roles Classification
Biological Roles:
CB1 receptor antagonist  An antagonist that binds to and deactivates type 1 cannabinoid receptors.
anti-obesity agent  Any substance which is used to reduce or control weight.
Application:
appetite depressant  Any agent that is used to decrease appetite.
ChEBI Ontology
Outgoing Relation(s)
rimonabant (CHEBI:34967) has role anti-obesity agent (CHEBI:74518)
rimonabant (CHEBI:34967) has role appetite depressant (CHEBI:50507)
rimonabant (CHEBI:34967) has role CB1 receptor antagonist (CHEBI:73416)
rimonabant (CHEBI:34967) is a amidopiperidine (CHEBI:48613)
rimonabant (CHEBI:34967) is a carbohydrazide (CHEBI:35363)
rimonabant (CHEBI:34967) is a dichlorobenzene (CHEBI:23697)
rimonabant (CHEBI:34967) is a monochlorobenzenes (CHEBI:83403)
rimonabant (CHEBI:34967) is a pyrazoles (CHEBI:26410)
IUPAC Name 
5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide
INNs  Source
rimonabantWHO MedNet
rimonabantumWHO MedNet
rimonabantWHO MedNet
rimonabantWHO MedNet
Synonyms  Source
SR 141716ChemIDplus
SR141716ChemIDplus
N-(1-piperidinyl)-1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxamideChEBI
5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamideChEBI
A 281ChEBI
Brand Names  Source
ZimultiChemIDplus
AcompliaChemIDplus
Manual XrefsDatabases
C14319KEGG COMPOUND
D05731KEGG DRUG
LSM-36994LINCS
4150DrugCentral
HMDB0015623HMDB
C00053749KNApSAcK
DB06155DrugBank
RimonabantWikipedia
AY6PDBeChem
94641ChemSpider
Registry NumbersSources
CAS:168273-06-1ChemIDplus
CAS:168273-06-1NIST Chemistry WebBook
Citations