(2S)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide

• ChemBase ID: 162035
• Molecular Formular: C18H14F4N2O4S
• Molecular Mass: 430.3733728
• Monoisotopic Mass: 430.06104082
• SMILES: c1c(c(ccc1NC(=O)[C@@](CS(=O)(=O)c1ccc(cc1)F)(O)C)C#N)C(F)(F)F
• Canonical 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)/t17-/m1/s1
• InChIKey: LKJPYSCBVHEWIU-QGZVFWFLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide
• IUPAC Traditional name: (2S)-N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfonyl)-2-hydroxy-2-methylpropanamide
• Synonyms: (2R)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl-d4)sulfonyl]-2-hydroxy-2-methylpropanamide; (R)-Casodex-d4; (R)-Bicalutamide-d4

Database IDs

• PubChem SID: 162256170
• PubChem CID: 441405

CALCULATED PROPERTIES

• Acid pKa: 11.947144
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.7092955
• LogD (pH = 7.4): 2.7092834
• Log P: 2.7092955
• Molar Refractivity: 96.5895 cm^3
• Polarizability: 36.135174 Å^3
• Polar Surface Area: 107.26 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate
• Apperance: Off-White Crystalline Solid
• Melting Point: 178-181°C

DETAILS

Toronto Research Chemicals - B382007

Labelled (R)-enantiomer of Bicalutamide. Used as an antiandrogen, antineoplastic (hormonal).

REFERENCES

• Tucker, H., et al.: J. Med. Chem., 31, 954 (1988)
• Cockshott, I.D., et al.: Eur. Urol., 18, Suppl. 3, 10 (1988)
• Cockshott, I., et al.: Br. J. Clin. Pharm., 36, 339 (1988)
• McKillop, D., et al.: Xenobiotica, 25, 623 (1988)