4-{3-[3-cyano-4-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl}-2-fluoro-N-(2H3)methylbenzamide

• ChemBase ID: 172562
• Molecular Formular: C21H16F4N4O2S
• Molecular Mass: 464.4359528
• Monoisotopic Mass: 464.09300965
• SMILES: C1(=O)C(N(C(=S)N1c1ccc(c(c1)C#N)C(F)(F)F)c1cc(c(cc1)C(=O)NC)F)(C)C
• Canonical SMILES: CNC(=O)c1ccc(cc1F)N1C(=S)N(C(=O)C1(C)C)c1ccc(c(c1)C#N)C(F)(F)F
• InChI: InChI=1S/C21H16F4N4O2S/c1-20(2)18(31)28(12-5-7-15(21(23,24)25)11(8-12)10-26)19(32)29(20)13-4-6-14(16(22)9-13)17(30)27-3/h4-9H,1-3H3,(H,27,30)
• InChIKey: BWQIAHIDLBLTGG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{3-[3-cyano-4-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl}-2-fluoro-N-(^2H₃)methylbenzamide
• IUPAC Traditional name: 4-{3-[3-cyano-4-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-sulfanylideneimidazolidin-1-yl}-2-fluoro-N-(^2H₃)methylbenzamide
• Synonyms: 4-[3-[4-Cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-4-oxo-2-thioxo-1-imidazolidinyl]-2-fluoro-N-(methyl-d3)benzamide; MDV 3100-d3

Database IDs

• PubChem SID: 164228472
• PubChem CID: 71749914

CALCULATED PROPERTIES

• Acid pKa: 13.054718
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.1554112
• LogD (pH = 7.4): 4.1554103
• Log P: 4.1554112
• Molar Refractivity: 113.4796 cm^3
• Polarizability: 41.52901 Å^3
• Polar Surface Area: 76.44 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M199802

Labelled MDV 3100. MDV 3100 is an androgen-receptor antagonist that blocks androgens from binding to the androgen receptor and prevents nuclear translocation and co-activator recruitment of the ligand-receptor complex. MDV 3100 has also been shown to ind

REFERENCES

• Scher, H.I. et al.: Lancet, 375, 1437 (2010)
• Bellmunt, J. et al.: Ther. Adv. Med. Oncol., 2, 189 (2010)
• Ryan, C.J. et al.: J. Clin. Oncol., 29, 3651 (2010)