4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzene-1-sulfonamide

• ChemBase编号: 462
• 分子式: C16H14N2O3S
• 平均质量: 314.35896
• 单一同位素质量: 314.07251332
• SMILES: S(=O)(=O)(N)c1ccc(c2c(noc2C)c2ccccc2)cc1
• Canonical SMILES: Cc1onc(c1c1ccc(cc1)S(=O)(=O)N)c1ccccc1
• InChI: InChI=1S/C16H14N2O3S/c1-11-15(12-7-9-14(10-8-12)22(17,19)20)16(18-21-11)13-5-3-2-4-6-13/h2-10H,1H3,(H2,17,19,20)
• InChIKey: LNPDTQAFDNKSHK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzene-1-sulfonamide
• IUPAC传统名: valdecoxib
• 商标名: Bextra
• 别名: valdecoxib; Valdecoxib; 4-(5-METHYL-3-PHENYLISOXAZOL-4-YL)BENZENESULFONAMIDE; SC-65872; YM-974; 4-(5-Methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide; Valdecoxib; Bextra; SC 65872; Valecoxib; Valus; Valz; 4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)benzenesulfonamide

登记号

• CAS号: 181695-72-7
• MDL号: MFCD00950568
• PubChem SID: 160963925; 46506229
• PubChem CID: 119607

理论计算性质

JChem

• Acid pKa: 10.057539
• 质子受体: 3
• 质子供体: 1
• LogD (pH = 5.5): 2.8236701
• LogD (pH = 7.4): 2.8228388
• Log P: 2.8236845
• 摩尔折射率: 84.708 cm^3
• 极化性: 35.26279 Å^3
• 极化表面积: 86.19 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: 3.32
• LOG S: -3.96
• 溶解度: 3.48e-02 g/l

分子性质

理化性质

• 溶解度: Acetone; DMSO: >25 mg/mL; Ethanol; Methanol
• 外观: White Solid; white to off-white powder
• 熔点: 162-164°C
• 疏水性(logP): 3.2

安全信息

• 保存条件: Refrigerator
• 欧盟危险性物质标志: 环境危害性(Nature polluting) (N); 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 63-48/22-51/53
• 安全公开号: 36/37-61
• GHS危险品标识: GHS08; GHS09
• GHS警示词: Warning
• GHS危险声明: H361d-H373-H410
• GHS警示性声明: P273-P281-P501
• 保存温度: room temp

药理学性质

• 作用靶点: COX

产品相关信息

• 纯度: ≥98% (HPLC); 98%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C16H14N2O3S

详细说明

DrugBank - DB00580

• Drug Groups: withdrawn; investigational
• Description: Valdecoxib was removed from the Canadian, U.S., and E.U. markets in 2005 due to concerns about possible increased risk of heart attack and stroke.
• Indication: For the treatment of osteoarthritis and dysmenorrhoea
• Pharmacology: Valdecoxib, a selective cyclooxygenase-2 (COX-2) inhibitor, is classified as a nonsteroidal anti-inflammatory drug (NSAID). Valdecoxib is used for its anti-inflammatory, analgesic, and antipyretic activities in the management of osteoarthritis (OA) and for the treatment of dysmenorrhea or acute pain. Unlike celecoxib, valdecoxib lacks a sulfonamide chain and does not require CYP450 enzymes for metabolism.
• Toxicity: Symptoms following acute NSAID overdoses are usually limited to lethargy, drowsiness, nausea, vomiting, and epigastric pain, which are generally reversible with supportive care. Gastrointestinal bleeding can occur. Hypertension, acute renal failure, respiratory depression and coma may occur, but are rare.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic (involves CYP3A4 and 2C9)
• Absorption: Oral bioavailability is 83%.
• Half Life: 8-11 hours
• Protein Binding: 98%
• Elimination: Valdecoxib is eliminated predominantly via hepatic metabolism with less than 5% of the dose excreted unchanged in the urine and feces. About 70% of the dose is excreted in the urine as metabolites, and about 20% as valdecoxib N-glucuronide.
• Distribution: * 86 L
• Clearance: * oral cl=6 L/h; * 6 – 7 L/h [In patients undergoing hemodialysis]; * 6 – 7 L/h [healthy elderly subjects]
• External Links: Wikipedia; RxList; Drugs.com

DrugBank - DB07576

Drug information: experimental

Sigma Aldrich - PZ0179

Biochem/physiol Actions
Valdecoxib is a non-steroidal anti-inflammatory drug (NSAID), a cyclooxygenase-2 (COX-2) selective inhibitor.
Legal Information
Sold for research purposes under agreement from Pfizer Inc.

Toronto Research Chemicals - V090000

A nonsteroidal anti-inflammatory drug (NSAID) that exhibits anti-inflammatory, analgesic and antipyretic properties in animal models. An inhibitor of prostaglandin synthesis primarily through inhibition of COX-2.

参考文献

• Yuan, J., et al.: Drug Metab. Dispos., 30, 1013 (2002)
• Mahadik, K., et al.: J. Pharm. Biomed. Anal., 33, 545 (2002)
• Kaul, N., et al.: J. Pharm. Biomed. Anal., 37, 27 (2002)