2-hydroxy-2-(2H3)methyl-N-[4-nitro-3-(trifluoromethyl)phenyl](2H3)propanamide

• ChemBase ID: 170593
• Molecular Formular: C11H11F3N2O4
• Molecular Mass: 292.2112496
• Monoisotopic Mass: 292.0670915
• SMILES: c1cc(c(cc1NC(=O)C(O)(C)C)C(F)(F)F)[N+](=O)[O-]
• Canonical SMILES: O=C(C(O)(C)C)Nc1ccc(c(c1)C(F)(F)F)[N+](=O)[O-]
• InChI: InChI=1S/C11H11F3N2O4/c1-10(2,18)9(17)15-6-3-4-8(16(19)20)7(5-6)11(12,13)14/h3-5,18H,1-2H3,(H,15,17)
• InChIKey: YPQLFJODEKMJEF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-2-(^2H₃)methyl-N-[4-nitro-3-(trifluoromethyl)phenyl](^2H₃)propanamide
• IUPAC Traditional name: 2-hydroxy-2-(^2H₃)methyl-N-[4-nitro-3-(trifluoromethyl)phenyl](^2H₃)propanamide
• Synonyms: 2-Hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide-d6; Hydroxyniphtholide-d6; Sch 16423-d6; α,α,α-Trifluoro-2-methyl-4'-nitro-m-lactotoluidide-d6; Hydroxy Flutamide-d6

Database IDs

• PubChem SID: 164226503
• PubChem CID: 10756473

CALCULATED PROPERTIES

• Acid pKa: 12.042255
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.2130709
• LogD (pH = 7.4): 2.2130616
• Log P: 2.2130709
• Molar Refractivity: 65.1288 cm^3
• Polarizability: 22.863628 Å^3
• Polar Surface Area: 95.15 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ether; Ethyl Acetate; Methanol
• Apperance: Light Yellow Solid
• Melting Point: 150-152°C

DETAILS

Toronto Research Chemicals - H942477

The active labelled metabolite of the widely used non-steroidal antagonist Flutamide (F598850). Shown to be an antianhydrogen. The current lot contains 0.5% d0

REFERENCES

• Katchen, B., et al.: J. Clin. Endocrinol. Metab., 41, 373 (1975)
• Fau, D., et al.: J. Pharmacol. Exp. Ther., 269, 954 (1975)
• Anzenbacher, P., et al.: Drug Metab. Dispos., 30, 100 (1975)
• Norlin, M., et al.: J. Lipid Res., 43, 721 (1975)