2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid

• ChemBase编号: 1141
• 分子式: C15H13ClFNO2
• 平均质量: 293.7206232
• 单一同位素质量: 293.06188456
• SMILES: Clc1c(Nc2c(cc(cc2)C)CC(=O)O)c(F)ccc1
• Canonical SMILES: OC(=O)Cc1cc(C)ccc1Nc1c(F)cccc1Cl
• InChI: InChI=1S/C15H13ClFNO2/c1-9-5-6-13(10(7-9)8-14(19)20)18-15-11(16)3-2-4-12(15)17/h2-7,18H,8H2,1H3,(H,19,20)
• InChIKey: KHPKQFYUPIUARC-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-{2-[(2-chloro-6-fluorophenyl)amino]-5-methylphenyl}acetic acid
• IUPAC传统名: lumiracoxib
• 商标名: Prexige (Novartis); Prexige
• 别名: lumiracoxib; COX 189; Lumiracoxib; 2-[(2-Chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic Acid; 2-[2-(2-Chloro-6-fluorophenylamino)-5-methylphenyl]acetic Acid; CGS 35189; Prexige; Lumiracoxib (COX-189)

登记号

• CAS号: 220991-20-8
• PubChem SID: 46506378; 160964604
• PubChem CID: 151166

理论计算性质

JChem

• Acid pKa: 4.114901
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 2.911556
• LogD (pH = 7.4): 1.2215736
• Log P: 4.311088
• 摩尔折射率: 75.9142 cm^3
• 极化性: 28.60001 Å^3
• 极化表面积: 49.33 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 4.56
• LOG S: -4.73
• 溶解度: 5.49e-03 g/l

分子性质

理化性质

• 溶解度: DMSO
• 外观: Pale Yellow Solid
• 熔点: 139-141°C
• 疏水性(logP): 3.9

安全信息

• 保存条件: -20°C Freezer

药理学性质

• 作用靶点: COX

产品相关信息

• 成盐信息: Free Base

详细说明

DrugBank - DB01283

• Drug Groups: approved; investigational
• Description: Lumiracoxib is a COX-2 selective inhibitor non-steroidal anti-inflammatory drug. On August 11, 2007, Australia's Therapeutic Goods Administration (TGA, the Australian equivalent of the FDA) cancelled the registration of lumiracoxib in Australia due to concerns that it may cause liver failure. New Zealand and Canada have also followed suit in recalling the drug.
• Indication: For the acute and chronic treatment of the signs and symptoms of osteoarthritis of the knee in adults.
• Pharmacology: Lumiracoxib has a different structure from the standard COX-2 inhibitors (e.g. celecoxib). It more closely resembles the structure of diclofenac (one chlorine substituted by fluorine, the phenylacetic acid has another methyl group in meta position), making it a member of the arylalkanoic acid family of NSAIDs. It binds to a different site on the COX-2 receptor than the standard COX-2 inhibitors. It displays extremely high COX-2 selectivity.
• Toxicity: Single oral doses in mice and rats resulted in mortality and/or moribundity at doses of 600 mg/kg and 500 mg/kg, respectively. Single intraperitoneal doses in mice and rats results in mortality/moribundity at 750 mg/kg and 1000 mg/kg, respectively. The maximum non-lethal single oral and intraperitoneal dose in mouse was 300 mg/kg and 250 mg/kg, respectively. In the rat it was 150 mg/kg and 250 mg/kg, respectively.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic oxidation and hydroxylation via CYP2C9. Three major metabolites have been identified in plasma: 4'-hydroxy-lumiracoxib, 5-carboxy-lumiracoxib, and 4'-hydroxy-5-carboxy-lumiracoxib.
• Absorption: Rapidly absorbed following oral administration, with an absolute oral bioavailablity of 74%.
• Half Life: Terminal half-life is approximately 4 hours.
• Protein Binding: Highly bound to plasma proteins (>= 98%).
• External Links: Wikipedia

Toronto Research Chemicals - L474700

Selective cyclooxygenase-2-(COX-2) inhibitor. Anti-inflammatory.

参考文献

• Bitner, M., et al.: Int. J. Clin. Pract., 58, 340 (2004)
• Packman, E., et al.: Headache, 45, 1163 (2004)
• Rordorf, C.M., et al.: Clin. Pharmacokinet., 44. 1247 (2004)
• Schnitzer, T.J., et al.: Curr. Med. Res. Opin., 21, 151 (2004)