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CHEBI:34967 - rimonabant

Default Structure
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 It was later withdrawn from market due to CNS-related adverse effects including depression and suicidal ideation.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:
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
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.
Applications:
hypoglycemic agent  A drug which lowers the blood glucose level.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
cardiovascular drug  A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
appetite depressant  Any agent that is used to decrease appetite.
ChEBI Ontology
Outgoing Relation(s)
rimonabant (CHEBI:34967) has role analgesic (CHEBI:35480)
rimonabant (CHEBI:34967) has role anti-obesity agent (CHEBI:74518)
rimonabant (CHEBI:34967) has role appetite depressant (CHEBI:50507)
rimonabant (CHEBI:34967) has role cardiovascular drug (CHEBI:35554)
rimonabant (CHEBI:34967) has role CB1 receptor antagonist (CHEBI:73416)
rimonabant (CHEBI:34967) has role hypoglycemic agent (CHEBI:35526)
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
rimonabantWHO MedNet
rimonabantWHO MedNet
rimonabantumWHO MedNet
Synonyms  Source
5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamideChEBI
A 281ChEBI
N-(1-piperidinyl)-1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxamideChEBI
SR-14171ChEMBL
SR 141716ChemIDplus
SR-141716ChEMBL
Brand Names  Source
AcompliaChemIDplus
ZimultiChemIDplus
Manual XrefsDatabases
4150DrugCentral
94641ChemSpider
AY6PDBeChem
C00053749KNApSAcK
C14319KEGG COMPOUND
D05731KEGG DRUG
DB06155DrugBank
HMDB0015623HMDB
LSM-36994LINCS
RimonabantWikipedia
Registry NumbersSources
CAS:168273-06-1ChemIDplus
CAS:168273-06-1NIST Chemistry WebBook
Citations