taranabant   Click here for help

GtoPdb Ligand ID: 9231

Synonyms: MK 0364 | MK-0364
PDB Ligand
Compound class: Synthetic organic
Comment: Taranabant is a cannabinoid CB1 receptor antagonist/inverse agonist [2-3], with anorectic action. It was investigated for its potential as a novel weight management therapeutic in obese and overweight patients.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 75.01
Molecular weight 515.16
XLogP 6.56
No. Lipinski's rules broken 1
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Canonical SMILES N#Cc1cccc(c1)C(C(NC(=O)C(Oc1ccc(cn1)C(F)(F)F)(C)C)C)Cc1ccc(cc1)Cl
Isomeric SMILES N#Cc1cccc(c1)[C@@H]([C@@H](NC(=O)C(Oc1ccc(cn1)C(F)(F)F)(C)C)C)Cc1ccc(cc1)Cl
InChI InChI=1S/C27H25ClF3N3O2/c1-17(34-25(35)26(2,3)36-24-12-9-21(16-33-24)27(29,30)31)23(14-18-7-10-22(28)11-8-18)20-6-4-5-19(13-20)15-32/h4-13,16-17,23H,14H2,1-3H3,(H,34,35)/t17-,23+/m0/s1
1. Addy C, Wright H, Van Laere K, Gantz I, Erondu N, Musser BJ, Lu K, Yuan J, Sanabria-Bohórquez SM, Stoch A et al.. (2008)
The acyclic CB1R inverse agonist taranabant mediates weight loss by increasing energy expenditure and decreasing caloric intake.
Cell Metab, 7 (1): 68-78. [PMID:18177726]
2. Foloppe N, Benwell K, Brooks TD, Kennett G, Knight AR, Misra A, Monck NJ. (2009)
Discovery and functional evaluation of diverse novel human CB(1) receptor ligands.
Bioorg Med Chem Lett, 19 (15): 4183-90. [PMID:19520572]
3. Lin LS, Ha S, Ball RG, Tsou NN, Castonguay LA, Doss GA, Fong TM, Shen CP, Xiao JC, Goulet MT et al.. (2008)
Conformational analysis and receptor docking of N-[(1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-{[5-(trifluoromethyl)pyridin-2-yl]oxy}propanamide (taranabant, MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist.
J Med Chem, 51 (7): 2108-14. [PMID:18333607]