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 For this reason sibutramine has been withdrawn from use in some countries.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
1. Auerbach SS, DrugMatrix® and ToxFX® Coordinator National Toxicology Program. 
National Toxicology Program: Dept of Health and Human Services.
Accessed on 02/05/2014. Modified on 02/05/2014. DrugMatrix,
2. Bae SH, Kwon MJ, Choi EJ, Zheng YF, Yoon KD, Liu KH, Bae SK. (2013)
Potent inhibition of cytochrome P450 2B6 by sibutramine in human liver microsomes.
Chem Biol Interact, 205 (1): 11-9. [PMID:23777987]
3. Kim SE, Ahn HS, Choi BH, Jang HJ, Kim MJ, Rhie DJ, Yoon SH, Jo YH, Kim MS, Sung KW, Hahn SJ. (2007)
Open channel block of A-type, kv4.3, and delayed rectifier K+ channels, Kv1.3 and Kv3.1, by sibutramine.
J Pharmacol Exp Ther, 321 (2): 753-62. [PMID:17312186]