rimonabant   

GtoPdb Ligand ID: 743

Synonyms: A 281 | Acomplia® | SR 141716
rimonabant is an approved drug (EMA (2007))
Compound class: Synthetic organic
Comment: EMA-only approval in 2007 withdrawn on 16 January 2009
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 49.64
Molecular weight 462.08
XLogP 6.13
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES Clc1ccc(cc1)c1c(C)c(nn1c1ccc(cc1Cl)Cl)C(=O)NN1CCCCC1
Isomeric SMILES Clc1ccc(cc1)c1c(C)c(nn1c1ccc(cc1Cl)Cl)C(=O)NN1CCCCC1
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)
InChI Key JZCPYUJPEARBJL-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (EMA (2007))
Withdrawn drug? Yes
IUPAC Name
5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide
International Nonproprietary Names
INN number INN
8029 rimonabant
Synonyms
A 281 | Acomplia® | SR 141716
Comments
EMA-only approval in 2007 withdrawn on 16 January 2009
Database Links
CAS Registry No. 158681-13-1 (source: DrugBank)
ChEBI CHEBI:116088
ChEMBL Ligand CHEMBL111
DrugBank Ligand DB06155
DrugCentral Ligand 4150
GtoPdb PubChem SID 135650901
PubChem CID 104850
RCSB PDB Ligand AY6
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Search UniChem for chemical match using the InChIKey JZCPYUJPEARBJL-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone JZCPYUJPEARBJL
Wikipedia Rimonabant