5-methyl-N-[4-(trifluoromethyl)(2H4)phenyl]-1,2-oxazole-4-carboxamide

• ChemBase ID: 172257
• Molecular Formular: C12H9F3N2O2
• Molecular Mass: 270.2072696
• Monoisotopic Mass: 270.0616122
• SMILES: c1noc(c1C(=O)Nc1ccc(cc1)C(F)(F)F)C
• Canonical SMILES: O=C(c1cnoc1C)Nc1ccc(cc1)C(F)(F)F
• InChI: InChI=1S/C12H9F3N2O2/c1-7-10(6-16-19-7)11(18)17-9-4-2-8(3-5-9)12(13,14)15/h2-6H,1H3,(H,17,18)
• InChIKey: VHOGYURTWQBHIL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-methyl-N-[4-(trifluoromethyl)(^2H₄)phenyl]-1,2-oxazole-4-carboxamide
• IUPAC Traditional name: 5-methyl-N-[4-(trifluoromethyl)(^2H₄)phenyl]-1,2-oxazole-4-carboxamide
• Synonyms: 5-Methylisoxazole-4-[4-trifluoromethylcarboxanilide]-d4; Leflunomida-d4; 5-Methyl-N-[4-(trifluoromethyl)phenyl]-4-isoxazolecarboxamide-d4; Leflunomidum-d4; Leflunomide-d4

Database IDs

• PubChem SID: 164228167
• PubChem CID: 45039652

CALCULATED PROPERTIES

• Acid pKa: 10.412348
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.5070803
• LogD (pH = 7.4): 2.506685
• Log P: 2.5070858
• Molar Refractivity: 64.1569 cm^3
• Polarizability: 22.013683 Å^3
• Polar Surface Area: 55.13 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ether; Ethyl Acetate; Methanol
• Apperance: Off White Crystalline Solid
• Melting Point: 161-163°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - L322752

An immunosuppressive. Inhibits T and B cell proliferation. Activity is attributed mainly to its metabolite, a malononitrile derivative, which is beleived to inhibit dihydroorotate dehydrogenase as well as several protein tyrosine kinases.

REFERENCES

• Vrenken, T., et al.: J. Hepatol., 49, 799 (2008)
• Mazzucco, G., et al.: Clin. Nephrol., 70, 163 (2008)
• Davies, M., et al.: J. Med. Chem., 52, 2683 (2008)