(2S,3S,4S,5R,6S)-6-(1-{[4-cyano-3-(trifluoromethyl)phenyl]carbamoyl}-2-(4-fluorobenzenesulfonyl)-1-methylethoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 162037
• Molecular Formular: C24H22F4N2O10S
• Molecular Mass: 606.4974928
• Monoisotopic Mass: 606.09312879
• SMILES: c1c(c(ccc1NC(=O)C(CS(=O)(=O)c1ccc(cc1)F)(O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)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@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C
• InChI: InChI=1S/C24H22F4N2O10S/c1-23(10-41(37,38)14-6-3-12(25)4-7-14,40-21-18(33)16(31)17(32)19(39-21)20(34)35)22(36)30-13-5-2-11(9-29)15(8-13)24(26,27)28/h2-8,16-19,21,31-33H,10H2,1H3,(H,30,36)(H,34,35)/t16-,17-,18+,19-,21-,23?/m0/s1
• InChIKey: OYKHNYWINRLUAP-CQNXPSKISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-(1-{[4-cyano-3-(trifluoromethyl)phenyl]carbamoyl}-2-(4-fluorobenzenesulfonyl)-1-methylethoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-(1-{[4-cyano-3-(trifluoromethyl)phenyl]carbamoyl}-2-(4-fluorobenzenesulfonyl)-1-methylethoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (2S)-N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl-d4)sulfonyl]-2-hydroxy-2-methylpropanamide; (S)-Casodex-d4; (S)-Bicalutamide-d4

Database IDs

• PubChem SID: 162256172
• PubChem CID: 71313964

CALCULATED PROPERTIES

• Acid pKa: 2.7488427
• H Acceptors: 11
• H Donor: 5
• LogD (pH = 5.5): -1.4262686
• LogD (pH = 7.4): -2.2391179
• Log P: 1.2587345
• Molar Refractivity: 128.8702 cm^3
• Polarizability: 49.97866 Å^3
• Polar Surface Area: 203.48 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Ethyl Acetate
• Apperance: Off-White Crystalline Solid
• Melting Point: 175-179°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B382012

Labelled (S)-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)