2-[(2,3-dimethylphenyl)amino]benzoic acid

• ChemBase编号: 664
• 分子式: C15H15NO2
• 平均质量: 241.2851
• 单一同位素质量: 241.11027873
• SMILES: OC(=O)c1c(Nc2c(c(ccc2)C)C)cccc1
• Canonical SMILES: OC(=O)c1ccccc1Nc1cccc(c1C)C
• InChI: InChI=1S/C15H15NO2/c1-10-6-5-9-13(11(10)2)16-14-8-4-3-7-12(14)15(17)18/h3-9,16H,1-2H3,(H,17,18)
• InChIKey: HYYBABOKPJLUIN-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-[(2,3-dimethylphenyl)amino]benzoic acid
• IUPAC传统名: mefenamic acid
• 商标名: Bafameritin-M; Bafhameritin-M; Bonabol; Coslan; HL 1; In-M; Lysalgo; Mefacit; Namphen; Parkemed; Ponalar; Ponstan; Ponstan Forte; Ponstel; Ponstil; Ponstyl; Pontal; Tamany Bonsan; Tanston; Vialidon; Ponstel, Ponstan
• 别名: 2-[(2,3-Dimethylphenyl)amino]-benzoic Acid; Mefacit; Mefenamic acid; Acide Mefenamique; Mefanamic Acid; Mefenacid; Mefenaminsaeure; Mephenamic Acid; Mephenaminic Acid; Methenamic Acid; Mefenamic acid; 2-((2,3-Dimethylphenyl)amino)benzoic acid; 2-[(2,3-Dimethylphenyl)amino]benzoic acid

登记号

• CAS号: 61-68-7
• EC号: 200-513-1
• MDL号: MFCD00051721
• PubChem SID: 46505405; 24896815; 160964127
• PubChem CID: 4044
• ATC码: M01AG01
• CHEMBL: 686
• Chemspider ID: 3904
• DrugBank ID: DB00784
• IUPHAR配体索引: 2593
• KEGG ID: D00151
• 美国药典/FDA物质标识码: 367589PJ2C
• 维基百科标题: Mefenamic_acid
• Medline Plus: a681028

理论计算性质

JChem

• Acid pKa: 3.885851
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 3.7780464
• LogD (pH = 7.4): 2.176643
• Log P: 5.3975973
• 摩尔折射率: 71.8828 cm^3
• 极化性: 26.912666 Å^3
• 极化表面积: 49.33 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 4.58
• LOG S: -4.25
• 溶解度: 1.37e-02 g/l

分子性质

理化性质

• 溶解度: 20 mg/L; Acetone; Chloroform; Dichloromethane; Methanol
• 外观: Off-White to Pale Yellow Solid
• 熔点: 227-229°C; 230-231
• 疏水性(logP): 4.2

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• 保存注意事项: IRRITANT
• RTECS编号: CB4550000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22; R:22
• 安全公开号: S:36/37/39
• TSCA收录: false
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 作用靶点: COX
• 给药途径: Oral
• 生物利用度: 90%
• 排泄: Renal and fecal
• 半衰期: 2 hours
• 代谢: Hepatic (CYP2C9)
• 蛋白结合率: 90%
• 法定药品分级: ?-only (U.S.), POM in UK
• 妊娠期药物分类: C (Australia, United States)

产品相关信息

• 纯度: 95+%; 98%
• 成盐信息: Free Base

详细说明

MP Biomedicals - 02193920

(2-[(2,3-Dimethylphenyl)amino]benzoic acid)

DrugBank - DB00784

• Drug Groups: approved
• Description: A non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is an inhibitor of cyclooxygenase. [PubChem]
• Indication: For the treatment of rheumatoid arthritis, osteoarthritis, dysmenorrhea, and mild to moderate pain, inflammation, and fever.
• Pharmacology: Mefenamic acid, an anthranilic acid derivative, is a member of the fenamate group of nonsteroidal anti-inflammatory drugs (NSAIDs). It exhibits anti-inflammatory, analgesic, and antipyretic activities. Similar to other NSAIDs, mefenamic acid inhibits prostaglandin synthetase.
• Toxicity: Oral, rat LD₅₀: 740 mg/kg. Symptoms of overdose may include severe stomach pain, coffee ground-like vomit, dark stool, ringing in the ears, change in amount of urine, unusually fast or slow heartbeat, muscle weakness, slow or shallow breathing, confusion, severe headache or loss of consciousness.
• Affected Organisms: Humans and other mammals
• Biotransformation: Mefenamic acid undergoes metabolism by CYP2C9 to 3-hydroxymethyl mefenamic acid, and further oxidation to a 3-carboxymefenamic acid may occur. The activity of these metabolites has not been studied. Mefenamic acid is also glucuronidated directly.
• Absorption: Mefenamic acid is rapidly absorbed after oral administration.
• Half Life: 2 hours
• Protein Binding: 90%
• Elimination: The fecal route of elimination accounts for up to 20% of the dose, mainly in the form of unconjugated 3-carboxymefenamic acid.3 The elimination half-life of mefenamic acid is approximately two hours. Mefenamic acid, its metabolites and conjugates are primarily excreted by the kidneys. Both renal and hepatic excretion are significant pathways of elimination.
• Distribution: * 1.06 L/kg [Normal Healthy Adults (18-45 yr)]
• Clearance: * Oral cl=21.23 L/hr [Healthy adults (18-45 yrs)]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - M4267

Application
An NSAID. Circumvents MRP-mediated multidrug resistance. Specifically and significantly potentiates the cytotoxicity of anthracyclines (doxorubicin, daunorubicin and epirubicin), as well as teniposide, VP-16 and vincristine.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M4267.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - M205050

Anti-inflammatory; analgesic.

参考文献

• Winder, C.V., J. Pharmacol. Exp. Ther., 138, 405 (1962)