CHEBI:34967 - rimonabant

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ChEBI Name rimonabant
ChEBI ID CHEBI:34967
Definition A 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 It was later withdrawn from market due to CNS-related adverse effects including depression and suicidal ideation.
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Formula C22H21Cl3N4O
Net Charge 0
Average Mass 463.790
Monoisotopic Mass 462.07809
InChI InChI=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)
InChIKey JZCPYUJPEARBJL-UHFFFAOYSA-N
SMILES CC1=C(N(N=C1C(=O)NN1CCCCC1)C1=CC=C(Cl)C=C1Cl)C1=CC=C(Cl)C=C1
Roles Classification
Biological Role(s): anti-obesity agent
Any substance which is used to reduce or control weight.
CB1 receptor antagonist
An antagonist that binds to and deactivates type 1 cannabinoid receptors.
Application(s): appetite depressant
Agent that is used to decrease appetite.
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ChEBI Ontology
Outgoing 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 Sources
rimonabant WHO MedNet
rimonabant WHO MedNet
rimonabant WHO MedNet
rimonabantum WHO MedNet
Synonyms Sources
5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide ChEBI
A 281 ChEBI
N-(1-piperidinyl)-1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxamide ChEBI
SR 141716 ChemIDplus
SR141716 ChemIDplus
Brand Names Sources
Acomplia ChemIDplus
Zimulti ChemIDplus
Manual Xrefs Databases
4150 DrugCentral
94641 ChemSpider
AY6 PDBeChem
C00053749 KNApSAcK
C14319 KEGG COMPOUND
D05731 KEGG DRUG
DB06155 DrugBank
HMDB0015623 HMDB
LSM-36994 LINCS
Rimonabant Wikipedia
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Registry Numbers Types Sources
168273-06-1 CAS Registry Number NIST Chemistry WebBook
168273-06-1 CAS Registry Number ChemIDplus
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Last Modified
05 January 2021