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

• ChemBase ID: 94067
• Molecular Formular: C11H11F3N2O4
• Molecular Mass: 292.2112496
• Monoisotopic Mass: 292.0670915
• SMILES: N(c1cc(c(cc1)[N+](=O)[O-])C(F)(F)F)C(=O)C(C)(C)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-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
• IUPAC Traditional name: 2-hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide
• Synonyms: Hydroxyflutamide; 2-Hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide; 2-Hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]-propanamide; 2-Hydroxyflutamide; Hydroxyniphtholide; Sch 16423; a,a,a-Trifluoro-2-methyl-4′-nitro-m-lactotoluidide; Hydroxyflutamide; 2-Hydroxy-2-methyl-N-[4-nitro-3-(trifluoromethyl)phenyl]propanamide; α,α,α-Trifluoro-2-methyl-4'-nitro-m-lactotoluidide; Hydroxy Flutamide

Database IDs

• CAS Number: 52806-53-8
• MDL Number: MFCD00563126
• PubChem SID: 162080722
• PubChem CID: 91649

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: 22.863615 Å^3
• Polar Surface Area: 95.15 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO: >10 mg/mL; Ethyl Acetate; Methanol
• Apperance: white to tan powder; Yellow Solid
• Melting Point: 139-141°C

Safety Information

• Storage Condition: -20°C Freezer; desiccated
• Storage Warning: Irritant
• RTECS: TX1466250
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C11H11F3N2O4

DETAILS

Apollo Scientific Ltd - PC1193

Flutamide metabolite

Sigma Aldrich - H4166

Biochem/physiol Actions
Hydroxflutamide is an AR antagonist. Androgen receptors (ARs) are nuclear hormone receptors/transcription factors. Hydroxyflutamide is an androgen antagonist with publications going back to 1981. It is one of a few gold standard AR antagonists; activities of new antagonists are measured against hydroxyflutamide.

Toronto Research Chemicals - H942475

The active metabolite of the widely used non-steroidal antagonist Flutamide (F598850). Shown to be an antianhydrogen.

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)