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

• ChemBase ID: 2015
• Molecular Formular: C14H10F3NO2
• Molecular Mass: 281.2299096
• Monoisotopic Mass: 281.06636323
• SMILES: c1(ccccc1Nc1cc(ccc1)C(F)(F)F)C(=O)O
• Canonical SMILES: OC(=O)c1ccccc1Nc1cccc(c1)C(F)(F)F
• InChI: InChI=1S/C14H10F3NO2/c15-14(16,17)9-4-3-5-10(8-9)18-12-7-2-1-6-11(12)13(19)20/h1-8,18H,(H,19,20)
• InChIKey: LPEPZBJOKDYZAD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid
• IUPAC Traditional name: flufenamic acid
• Synonyms: 2-[[3-(Trifluoromethyl)phenyl]amino]benzoic Acid; 2-[3-(Trifluoromethyl)anilino]benzoic Acid; 3'-Trifluoromethyldiphenylamine-2-carboxylic Acid; Fullsafe; INF 1837; Meralen; Sastridex; Surika; Tecramine; Flufenamic Acid; FFA; Flufenamic acid; N-(α,α,α-Trifluoro-m-tolyl)anthranilic acid; N-(3-[Trifluoromethyl]phenyl)anthranilic acid; N-(3-Trifluoromethylphenyl)anthranilic acid; N-(3-[三氟甲基]苯基)邻氨基苯甲酸; N-(α,α,α-三氟-间甲苯基)邻氨基苯甲酸; 氟芬那酸

Database IDs

• CAS Number: 530-78-9; 570-78-9
• EC Number: 208-494-1
• MDL Number: MFCD00002422
• Beilstein Number: 1996069
• Merck Index: 144132
• PubChem SID: 160965470; 46507173; 24894982
• PubChem CID: 3371
• CHEBI ID: 42638
• ATC CODE: M01AG03
• CHEMBL: 23588
• Chemspider ID: 3254
• DrugBank ID: DB02266
• IUPHAR ligand ID: 2447
• KEGG ID: D01581
• Unique Ingredient Identifier: 60GCX7Y6BH
• Wikipedia Title: Flufenamic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.8783112
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.6219354
• LogD (pH = 7.4): 2.0239105
• Log P: 5.248603
• Molar Refractivity: 67.7741 cm^3
• Polarizability: 24.517488 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.6
• LOG S: -4.55
• Solubility (Water): 8.00e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.00909 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; DMSO; Methanol; Practically insoluble in water; soluble in ethanol, chloroform and diethyl ether
• Apperance: Pale-Yellow Solid
• Melting Point: 124-125 °C (255.2-257°F) (resolidification and remelting at 134°C to 136°C); 124-125°C; 129-131°C; 132-135 °C(lit.); 133-135°C
• Hydrophobicity(logP): 5.25 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• Storage Warning: Irritant/Keep Cold
• RTECS: CB4375000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2811; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 22-36/37/38; 22-36/38; R:22
• Safety Statements: 26; 26-36/37; S:36/37/39
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319; H302-H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Target: Others
• Admin Routes: oral, topical
• Excretion: 50% urine, 36% feces
• Half Life: ~3 h
• Metabolism: Hydroxylation, glucuronidation
• Protein Bound: extensively

Product Information

• Purity: 97%
• Grade: analytical standard, for drug analysis
• Salt Data: Free Base
• Linear Formula: 2-(CF3C6H4NH)C6H4CO2H

DETAILS

DrugBank - DB02266

• Drug Groups: experimental
• Description: An anthranilic acid derivative with analgesic, anti-inflammatory, and antipyretic properties. It is used in musculoskeletal and joint disorders and administered by mouth and topically. (From Martindale, The Extra Pharmacopoeia, 30th ed, p16)

Toronto Research Chemicals - F435000

Anti-inflammatory; analgesic.

REFERENCES

• Winder, et al.: Arthritis Rheum., 6, 36 (1963)
• Inglot, et al.: J. Gen. Virol., 4, 203 (1963)
• Zoni, et al.: Farmaco. Ed. Sci., 26, 191 (1963)
• Abignente, E., et al.: Anal. Profiles Drug Subs., 11, 313 (1963)