bicalutamide   

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
SMILES / InChI / InChIKey
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)
InChI Key LKJPYSCBVHEWIU-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
Used along with luteinizing hormone-releasing hormone analogs to treat metastatic prostate cancer.
Mechanism Of Action and Pharmacodynamic Effects
Bicalutamide acts by antagonising the proliferative actions of the adrenal and testicular androgens on normal and malignant prostatic tissue. Since most prostate cancers are androgen-dependent they are sensitive to this type of 'chemical castration'.
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