2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid

• ChemBase ID: 72735
• Molecular Formular: C16H16N2O3S
• Molecular Mass: 316.37484
• Monoisotopic Mass: 316.08816338
• SMILES: c1(c(ccc(c1)c1sc(c(n1)C)C(=O)O)OCC(C)C)C#N
• 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-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid
• IUPAC Traditional name: febuxostat
• Brand Name: Adenuric, Uloric , Febutaz
• Synonyms: 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid; 2-[3-Cyano-4-(2-methylpropoxy)phenyl]-4-methyl-5-thiazolecarboxylic Acid; 2-(3-Cyano-4-isobutyloxyphenyl)-4-methyl-5-thiazolecarboxylic Acid; TEI 6720; TMX 67; TMX-67; Adenuric; Uloric; Febuxostat; 2-(3-Cyano-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylic acid

Database IDs

• CAS Number: 144060-53-7
• MDL Number: MFCD00871598
• PubChem SID: 162037656
• PubChem CID: 134018
• ATC CODE: M04AA03
• CHEMBL: 1164729
• Chemspider ID: 118173
• KEGG ID: D01206
• Unique Ingredient Identifier: 101V0R1N2E
• Wikipedia Title: Febuxostat
• Medline Plus: a609020

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: 32.385162 Å^3
• Polar Surface Area: 83.21 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 208-209°(dec.)
• Hydrophobicity(logP): 4.097

Safety Information

• Storage Condition: -20°C; Refrigerator

Pharmacology Properties

• Target: XAO
• Admin Routes: oral
• Bioavailability: ~49% absorbed
• Excretion: urine (~49% mostly as metabolites, 3% as unchanged drug); feces (~45% mostly as metabolites, 12% as unchanged drug)
• Half Life: ~5-8 hours
• Metabolism: via CYP1A2, 2C8, 2C9, UGT1A1, 1A3, 1A9, 2B7
• Protein Bound: ~99% to albumin
• Legal Status: Rx-only (US)
• Pregnancy Category: C
• US Licence: Febuxostat
• EU Licence: Adenuric

Product Information

• Purity: 95%; 95+%
• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1547

Research Area: Metabolic Disease
Biological Activity:
Febuxostat (Uloric) is a non-purine selective XAO inhibitor with IC50 of 114 -210 nM.It works by non-competitively blocking the channel leading to the active site on xanthine oxidase. [1] Xanthine oxidase is needed to successively oxidize both hypoxanthine and xanthine to uric acid. Hence, febuxostat inhibits xanthine oxidase, therefore reducing production of uric acid. [2][3]

Toronto Research Chemicals - F229000

Xanthine oxidase/xanthine dehydrogenase inhibitor. Used for treatment of hyperuricemia and chronic gout.

REFERENCES

• Gaffo AL et al. Core Evid. 2010 Jun 15;4:25-36
• Tomlinson, B., et al.: Curr. Opin. Invest. Drugs, 6, 1168 (1993)
• 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)