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

• ChemBase ID: 162042
• Molecular Formular: C18H14F4N2O3S
• Molecular Mass: 414.3739728
• Monoisotopic Mass: 414.0661262
• SMILES: c1c(c(ccc1NC(=O)C(CS(=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)c1ccc(cc1)F)(O)C
• InChI: InChI=1S/C18H14F4N2O3S/c1-17(26,10-28(27)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)
• InChIKey: MHWPKBKCPXTKJS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfinyl)-2-hydroxy-2-methylpropanamide
• IUPAC Traditional name: N-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorobenzenesulfinyl)-2-hydroxy-2-methylpropanamide
• Synonyms: N-[4-Cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfinyl]-2-hydroxy-2-methylpropanamide; Bicalutamide Sulfoxide

Database IDs

• CAS Number: 945419-64-7
• PubChem SID: 162256177
• PubChem CID: 42604713

CALCULATED PROPERTIES

• Acid pKa: 12.114894
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.6024015
• LogD (pH = 7.4): 2.6023934
• Log P: 2.6024017
• Molar Refractivity: 97.5267 cm^3
• Polarizability: 35.498417 Å^3
• Polar Surface Area: 90.19 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B382045

An impurity of Bicalutamide (B382000); USP Related Compound A.

REFERENCES

• Tucker, H., et al.: J. Med. Chem., 31, 885 (1988)
• Cockshott, I., et al.: Br. J. Clin. Pharmacol., 36, 339 (1988)
• McKillop, D., et al.: Xenobiotica, 23, 1241 (1993)