2-{3-cyano-4-[2-(2H3)methyl(2H6)propoxy]phenyl}-4-methyl-1,3-thiazole-5-carboxylic acid

• ChemBase ID: 168872
• Molecular Formular: C16H16N2O3S
• Molecular Mass: 316.37484
• Monoisotopic Mass: 316.08816338
• SMILES: c1(c(cc(cc1)c1sc(c(n1)C)C(=O)O)C#N)OCC(C)C
• Canonical SMILES: N#Cc1cc(ccc1OCC(C)C)c1nc(c(s1)C(=O)O)C
• InChI: InChI=1S/C16H16N2O3S/c1-9(2)8-21-13-5-4-11(6-12(13)7-17)15-18-10(3)14(22-15)16(19)20/h4-6,9H,8H2,1-3H3,(H,19,20)
• InChIKey: BQSJTQLCZDPROO-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{3-cyano-4-[2-(^2H₃)methyl(^2H₆)propoxy]phenyl}-4-methyl-1,3-thiazole-5-carboxylic acid
• IUPAC Traditional name: 2-{3-cyano-4-[2-(^2H₃)methyl(^2H₆)propoxy]phenyl}-4-methyl-1,3-thiazole-5-carboxylic acid
• Synonyms: 2-[3-Cyano-4-(2-methylpropoxy-d9)phenyl]-4-methyl-5-thiazolecarboxylic Acid; 2-(3-Cyano-4-isobutyloxyphenyl-d9)-4-methyl-5-thiazolecarboxylic Acid; TEI 6720-d9; TMX 67-d9; Febuxostat-d9

Database IDs

• PubChem SID: 162263004
• PubChem CID: 49849690

CALCULATED PROPERTIES

• Acid pKa: 3.078274
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.1251484
• LogD (pH = 7.4): 0.055648725
• Log P: 3.5209293
• Molar Refractivity: 93.9288 cm^3
• Polarizability: 32.38571 Å^3
• Polar Surface Area: 83.21 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F229002

Labelled Febuxostat (F229000). Xanthine oxidase/xanthine dehydrogenase inhibitor. Used for treatment of hyperuricemia and chronic gout.

REFERENCES

• Osada, Y., et al.: Eur. J. Pharmacol., 241, 183 (1993)
• Okamoto, K., et al.: J. Biol. Chem., 278, 1848 (1993)
• Mayer, M.D., et al.: Am. J. Therap., 12, 22 (1993)
• Tomlinson, B., et al.: Curr. Opin. Invest. Drugs, 6, 1168 (1993)