(2Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)(2H4)phenyl]but-2-enamide

• ChemBase ID: 160809
• Molecular Formular: C12H9F3N2O2
• Molecular Mass: 270.2072696
• Monoisotopic Mass: 270.0616122
• SMILES: c1c(ccc(c1)C(F)(F)F)NC(=O)/C(=C(/C)\O)/C#N
• Canonical SMILES: N#C/C(=C(/O)\C)/C(=O)Nc1ccc(cc1)C(F)(F)F
• InChI: InChI=1S/C12H9F3N2O2/c1-7(18)10(6-16)11(19)17-9-4-2-8(3-5-9)12(13,14)15/h2-5,18H,1H3,(H,17,19)/b10-7-
• InChIKey: UTNUDOFZCWSZMS-YFHOEESVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)(^2H₄)phenyl]but-2-enamide
• IUPAC Traditional name: (2Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)(^2H₄)phenyl]but-2-enamide
• Synonyms: A77 1726-d4; N-(4-Trifluoromethylphenyl)-2-cyano-3-hydroxycrotonamide-d4, 2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-2-beuteamide-d4, LEF-M-d4; Teriflunomide-d4

Database IDs

• CAS Number: 1185240-22-5
• PubChem SID: 162254944
• PubChem CID: 71313485

CALCULATED PROPERTIES

• Acid pKa: 5.483075
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.8294411
• LogD (pH = 7.4): 0.2272011
• Log P: 2.138883
• Molar Refractivity: 64.3928 cm^3
• Polarizability: 22.244638 Å^3
• Polar Surface Area: 73.12 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Aqueous Alkali; DMSO
• Apperance: Off-White Solid
• Melting Point: 230-232°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A771727

The active metabolite of Leflunomide, a potent disease-modifying antirheumatic drug used in the treatment of rheumatoid arthritis. LEF-M interferes with dendritic cell function.

REFERENCES

• Kirsch, B.M., et al.: Arthritis Research and Therapy, 7, 3, R694, (2005)