rimonabant

Term ID

CHEBI:34967

Synonyms

• 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide
• 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide
• A 281
• Acomplia
• N-(1-piperidinyl)-1-(2,4-dichlorophenyl)-4-methyl-5-(4-chlorophenyl)-1H-pyrazole-3-carboxamide
• rimonabant
• rimonabantum
• SR 141716
• SR141716
• Zimulti

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 It was later withdrawn from market due to CNS-related adverse effects including depression and suicidal ideation.

References

• cas:168273-06-1
• chemspider:94641
• drugbank:DB06155
• drugcentral:4150
• hmdb:HMDB0015623
• kegg.compound:C14319
• kegg.drug:D05731
• knapsack:C00053749
• lincs.smallmolecule:LSM-36994
• pdb-ccd:AY6
• pubmed:11881536
• pubmed:16934319
• pubmed:18290515
• pubmed:18479080
• pubmed:18654765
• pubmed:19490094
• pubmed:20067470
• pubmed:20828968
• pubmed:21470203
• pubmed:21740450
• pubmed:22182934
• pubmed:28429843
• pubmed:29407764
• pubmed:29797785
• pubmed:30077950
• pubmed:30300803
• pubmed:30556096
• pubmed:30682372
• pubmed:31522677
• pubmed:31898189
• pubmed:31981244
• pubmed:32085406
• pubmed:32417279
• pubmed:32463562
• pubmed:32512776
• pubmed:32781169
• pubmed:32885412
• pubmed:32904155
• pubmed:33121353
• wikipedia.en:Rimonabant

Ontology

ChEBI  ( EBI )