sibutramine   Click here for help

GtoPdb Ligand ID: 2586

Synonyms: Meridia® | sibutramine hydrochloride
Approved drug
sibutramine is an approved drug (FDA (1997))
Compound class: Synthetic organic
Comment: Use of sibutramine is reported to increase risk of heart attack and stroke in patients with a history of heart disease. For this reason sibutramine has been withdrawn from use in some countries.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 3.24
Molecular weight 279.18
XLogP 5.17
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CC(CC(C1(CCC1)c1ccc(cc1)Cl)N(C)C)C
Isomeric SMILES CC(CC(C1(CCC1)c1ccc(cc1)Cl)N(C)C)C
InChI InChI=1S/C17H26ClN/c1-13(2)12-16(19(3)4)17(10-5-11-17)14-6-8-15(18)9-7-14/h6-9,13,16H,5,10-12H2,1-4H3
InChI Key UNAANXDKBXWMLN-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1997))
Withdrawn drug? Yes
IUPAC Name Click here for help
1-[1-(4-chlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine
International Nonproprietary Names Click here for help
INN number INN
6124 sibutramine
Synonyms Click here for help
Meridia® | sibutramine hydrochloride
Database Links Click here for help
CAS Registry No. 106650-56-0 (source: Scifinder)
ChEBI CHEBI:458192
ChEMBL Ligand CHEMBL1419
DrugBank Ligand DB01105
DrugCentral Ligand 2440
GtoPdb PubChem SID 135651043
PubChem CID 5210
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Wikipedia Sibutramine