5-chloro-3-(4-methanesulfonylphenyl)-2-(6-methylpyridin-3-yl)pyridine

• ChemBase编号: 1404
• 分子式: C18H15ClN2O2S
• 平均质量: 358.8419
• 单一同位素质量: 358.05427641
• SMILES: Clc1cc(c2ccc(S(=O)(=O)C)cc2)c(nc1)c1ccc(nc1)C
• Canonical SMILES: Clc1cnc(c(c1)c1ccc(cc1)S(=O)(=O)C)c1ccc(nc1)C
• InChI: InChI=1S/C18H15ClN2O2S/c1-12-3-4-14(10-20-12)18-17(9-15(19)11-21-18)13-5-7-16(8-6-13)24(2,22)23/h3-11H,1-2H3
• InChIKey: MNJVRJDLRVPLFE-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 5-chloro-3-(4-methanesulfonylphenyl)-2-(6-methylpyridin-3-yl)pyridine
• IUPAC传统名: etoricoxib
• 商标名: Arcoxia; Nucoxia; Tauxib; Algix
• 别名: 5-chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine; 5-Chloro-6'-methyl-3-[4-(methylsulfonyl)phenyl]-2,3'-bipyridine; Algix; Arcoxia; Etobrix; Etocox; Etoxib; Etropain; Kingcox; MK 0663; MK 663; Tauxib; Torcoxia; etoricoxib; MK-663; Etoricoxib

登记号

• CAS号: 202409-33-4
• PubChem SID: 160964864; 46504505
• PubChem CID: 123619
• CHEBI ID: 6339
• ATC码: M01AH05
• CHEMBL: 416146
• Chemspider ID: 110209
• DrugBank ID: DB01628
• KEGG ID: D03710
• 美国药典/FDA物质标识码: WRX4NFY03R
• 维基百科标题: Etoricoxib

理论计算性质

JChem

• Acid pKa: 19.693102
• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 2.6881886
• LogD (pH = 7.4): 2.7924058
• Log P: 2.7939253
• 摩尔折射率: 95.0445 cm^3
• 极化性: 40.067413 Å^3
• 极化表面积: 59.92 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.7
• LOG S: -5.04
• 溶解度: 3.28e-03 g/l

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: Off-White Solid
• 熔点: 135-138°C

安全信息

• 保存条件: -20°C Freezer

药理学性质

• 给药途径: Oral
• 生物利用度: 100%
• 排泄: Renal (70%) and fecal (20%)
• 半衰期: 22 hours
• 代谢: Hepatic, CYP extensively involved (mainly CYP3A4)
• 蛋白结合率: 92%
• 法定药品分级: POM (UK)
• 妊娠期药物分类: Not recommended

详细说明

DrugBank - DB07166

Drug information: experimental

DrugBank - DB01628

• Drug Groups: approved; investigational
• Description: Etoricoxib is a new COX-2 selective inhibitor. Current therapeutic indications are: treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout. Like any other COX-2 selective inhibitor, Etoricoxib selectively inhibits isoform 2 of cyclo-oxigenase enzyme (COX-2). This reduces the generation of prostaglandins (PGs) from arachidonic acid.
• Indication: For the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, chronic low back pain, acute pain and gout.
• Pharmacology: Etoricoxib is a COX-2 selective inhibitor (approximately 106 times more selective for COX-2 inhibition over COX-1). Currently it is approved in more than 60 countries worldwide but not in the US, where the Food and Drug Administration (FDA) require additional safety and efficacy data for etoricoxib before it will issue approval.
• Toxicity: This reduced activity is the cause of reduced gastrointestinal toxicity, as demonstrated in several large clinical trials performed with different COXIB (see below links on NEJM and The Lancet). Some clinical trials and meta-analysis showed that treatment with COXIB lead to increased incidence of cardiovascular adverse events compared to placebo
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic, primarily via CYP3A4.
• Absorption: Bioavailability is 100% following oral administration.
• Half Life: 22 hours
• Protein Binding: 92%
• External Links: Wikipedia

Toronto Research Chemicals - E934100

A specific inhibitor of COX-2 .

参考文献

• McGeer, P.L., et al.: Exp. Gerontol., 37, 925 (2002)
• Chenevard, R., et al.: Circulation, 107, 405 (2003)