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

• ChemBase编号: 72735
• 分子式: C16H16N2O3S
• 平均质量: 316.37484
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 2-[3-cyano-4-(2-methylpropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylic acid
• IUPAC传统名: febuxostat
• 商标名: Adenuric, Uloric , Febutaz
• 别名: 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

登记号

• CAS号: 144060-53-7
• MDL号: MFCD00871598
• PubChem SID: 162037656
• PubChem CID: 134018
• ATC码: M04AA03
• CHEMBL: 1164729
• Chemspider ID: 118173
• KEGG ID: D01206
• 美国药典/FDA物质标识码: 101V0R1N2E
• 维基百科标题: Febuxostat
• Medline Plus: a609020

理论计算性质

• Acid pKa: 3.078274
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 1.1251484
• LogD (pH = 7.4): 0.055648725
• Log P: 3.5209293
• 摩尔折射率: 93.9288 cm^3
• 极化性: 32.385162 Å^3
• 极化表面积: 83.21 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: Off-White Solid
• 熔点: 208-209°(dec.)
• 疏水性(logP): 4.097

安全信息

• 保存条件: -20°C; Refrigerator

药理学性质

• 作用靶点: XAO
• 给药途径: oral
• 生物利用度: ~49% absorbed
• 排泄: urine (~49% mostly as metabolites, 3% as unchanged drug); feces (~45% mostly as metabolites, 12% as unchanged drug)
• 半衰期: ~5-8 hours
• 代谢: via CYP1A2, 2C8, 2C9, UGT1A1, 1A3, 1A9, 2B7
• 蛋白结合率: ~99% to albumin
• 法定药品分级: Rx-only (US)
• 妊娠期药物分类: C
• 美国（FDA）药品许可证: Febuxostat
• 欧盟（EMEA）药品许可证: Adenuric

产品相关信息

• 纯度: 95%; 95+%
• 成盐信息: Free Base

详细说明

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.

参考文献

• 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)