2-{[3-(trifluoromethyl)phenyl]amino}pyridine-3-carboxylic acid

• ChemBase编号: 4120
• 分子式: C13H9F3N2O2
• 平均质量: 282.2179696
• 单一同位素质量: 282.0616122
• SMILES: FC(F)(F)c1cc(Nc2ncccc2C(=O)O)ccc1
• Canonical SMILES: OC(=O)c1cccnc1Nc1cccc(c1)C(F)(F)F
• InChI: InChI=1S/C13H9F3N2O2/c14-13(15,16)8-3-1-4-9(7-8)18-11-10(12(19)20)5-2-6-17-11/h1-7H,(H,17,18)(H,19,20)
• InChIKey: JZFPYUNJRRFVQU-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-{[3-(trifluoromethyl)phenyl]amino}pyridine-3-carboxylic acid
• IUPAC传统名: niflumic acid
• 商标名: Flogovital; Actol; Niflam; Nifluril; Landruma; Forenol
• 别名: 2-[[3-(Trifluoromethyl)phenyl]amino]-3-pyridinecarboxylic Acid; Actol (analgesic); Donalgin; Flogovital; UP 83; 2-(α,α,α-Trifluoro-m-toluidino)nicotinic acid; Niflumic acid; 2-((3-(Trifluoromethyl)phenyl)amino)nicotinic acid; 2-[(3-Trifluoromethyl)Phenyl]Amino-3-Pyridine-Carboxylic Acid; Niflumate; Nifluminic acid; NFL; NFA; Lopac-N-0630; Acidum niflumicum [inn-latin]; Acido niflumico [inn-spanish]; Acide niflumique [inn-french]; 2-[3-(Trifluoromethyl)anilino]nicotinic acid; 2-(alpha,alpha,alpha-Trifluoro-m-toluidino)nicotinic acid; 2-(3-Trifluoromethyl-phenylamino)-nicotinic acid; 2-(3-(Trifluoromethyl)anilino)nicotinic acid; 2-(3-(Trifluoromethyl)-phenyl)aminonicotinic acid; Niflumic Acid; 2-[alpha,alpha,alpha-trifluoro-m-toluidino]-nicotinic acid; Actol; Forenol; Landruma; Nifluril

登记号

• CAS号: 4394-00-7
• EC号: 224-516-2
• MDL号: MFCD00010569
• PubChem SID: 46504657; 160967552; 24278582
• PubChem CID: 4488

理论计算性质

JChem

• Acid pKa: 1.8800513
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 2.8410227
• LogD (pH = 7.4): 1.4721208
• Log P: 3.1187294
• 摩尔折射率: 65.9307 cm^3
• 极化性: 23.710608 Å^3
• 极化表面积: 62.22 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: 4.33
• LOG S: -3.5
• 溶解度: 8.83e-02 g/l

分子性质

理化性质

• 溶解度: 0.019 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; Sparingly Soluble in DMSO and Methanol
• 外观: Light Yellow Solid
• 熔点: 194-205°C; 199-204°C
• 疏水性(logP): 4.43 [TAKACS-NOVAK,K ET AL. (1995)]

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• 保存注意事项: IRRITANT
• RTECS编号: QT2999100
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 20/21/22-36/37/38; R:22
• 安全公开号: 26-36; 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-H312-H315-H319-H332-H335
• GHS警示性声明: P261-P280-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

药理学性质

• 作用靶点: GABA Receptor
• 相关基因信息: human ... PTGS1(5742)

产品相关信息

• 纯度: 95+%; 98%
• 成盐信息: Free Base

详细说明

DrugBank - DB04552

• Drug Groups: approved
• Description: An analgesic and anti-inflammatory agent used in the treatment of rheumatoid arthritis. [PubChem]
• Indication: Used in the treatment of rheumatoid arthritis.
• Pharmacology: Niflumic acid, a nonsteroidal anti-inflammatory fenamate, is a Ca^2+-activated Cl^- channel blocker.
• Toxicity: Oral, mouse: LD₅₀ = 350 mg/kg; Oral, rat: LD₅₀ = 250 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Absorption: Well absorbed following oral administration.
• Half Life: 2.5 hours
• Protein Binding: 90% bound to plasma proteins.
• References: Criddle DN, de Moura RS, Greenwood IA, Large WA: Inhibitory action of niflumic acid on noradrenaline- and 5-hydroxytryptamine-induced pressor responses in the isolated mesenteric vascular bed of the rat. Br J Pharmacol. 1997 Mar;120(5):813-8. [Pubmed]

Sigma Aldrich - N0630

Biochem/physiol Actions
Selective cyclooxygenase-2 (COX-2) inhibitor.

Toronto Research Chemicals - N457500

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

参考文献

• Criddle DN, de Moura RS, Greenwood IA, Large WA: Inhibitory action of niflumic acid on noradrenaline- and 5-hydroxytryptamine-induced pressor responses in the isolated mesenteric vascular bed of the rat. Br J Pharmacol. 1997 Mar;120(5):813-8. Pubmed
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