GtoPdb Ligand ID: 2863

Synonyms: Calutide® | Casodex®
bicalutamide is an approved drug (FDA (1995))
Compound class: Synthetic organic
Comment: Bicalutamide is non-steroidal anti-androgen that binds to the andogen receptor. The INN record for this drug indicates that it is a mixture of stereo-isomers. We show the non-stereo molecule to represent this mixture. (R)-Bicalutamide has PubChem CID 56069.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 7
Topological polar surface area 115.64
Molecular weight 430.06
XLogP 2.53
No. Lipinski's rules broken 0
Canonical SMILES N#Cc1ccc(cc1C(F)(F)F)NC(=O)C(CS(=O)(=O)c1ccc(cc1)F)(O)C
Isomeric SMILES N#Cc1ccc(cc1C(F)(F)F)NC(=O)C(CS(=O)(=O)c1ccc(cc1)F)(O)C
InChI InChI=1S/C18H14F4N2O4S/c1-17(26,10-29(27,28)14-6-3-12(19)4-7-14)16(25)24-13-5-2-11(9-23)15(8-13)18(20,21)22/h2-8,26H,10H2,1H3,(H,24,25)
1. Jung ME, Ouk S, Yoo D, Sawyers CL, Chen C, Tran C, Wongvipat J. (2010)
Structure-activity relationship for thiohydantoin androgen receptor antagonists for castration-resistant prostate cancer (CRPC).
J. Med. Chem., 53 (7): 2779-96. [PMID:20218717]
2. Kinoyama I, Taniguchi N, Toyoshima A, Nozawa E, Kamikubo T, Imamura M, Matsuhisa A, Samizu K, Kawanimani E, Niimi T et al.. (2006)
(+)-(2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6-(trifluoromethyl)pyridin-3- yl]piperazine-1-carboxamide (YM580) as an orally potent and peripherally selective nonsteroidal androgen receptor antagonist.
J. Med. Chem., 49 (2): 716-26. [PMID:16420057]