Flufenamic acid

Base Information

• Chemical Name: Flufenamic acid
• CAS No.: 530-78-9
• Molecular Formula: C14H10F3NO2
• Molecular Weight: 281.234
• Hs Code.: 29224999
• European Community (EC) Number: 208-494-1
• NSC Number: 757823,219007,82699
• UNII: 60GCX7Y6BH
• DSSTox Substance ID: DTXSID7023063
• Nikkaji Number: J2.064H
• Wikipedia: Flufenamic_acid
• Wikidata: Q416341
• NCI Thesaurus Code: C166882
• Pharos Ligand ID: 4GG5L8MY9B2H
• Metabolomics Workbench ID: 52321
• ChEMBL ID: CHEMBL23588
• Mol file: 530-78-9.mol

Synonyms:Acid, Flufenamic;Dignodolin;Flufenamic Acid

Chemical Property of Flufenamic acid

Chemical Property:

• Appearance/Colour: pale-yellow solid
• Vapor Pressure: 2.97E-06mmHg at 25°C
• Melting Point: 132-135 °C(lit.)
• Refractive Index: 1.585
• Boiling Point: 373.903 °C at 760 mmHg
• PKA: pKa 3.9 (Uncertain);3.85 (Uncertain)
• Flash Point: 179.93 °C
• PSA: 49.33000
• Density: 1.396 g/cm³
• LogP: 4.22020
• Storage Temp.: Refrigerator
• Solubility.: soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide. The solubility of flufenamic acid in these solvents is approximately 11, 39, and 59 mg/ml, respectively.
• Water Solubility.: 0.0265 g/L (37 ºC)
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 281.06636305
• Heavy Atom Count: 20
• Complexity: 346

Purity/Quality:

99%min ^*data from raw suppliers

Flufenamic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(=O)O)NC2=CC=CC(=C2)C(F)(F)F
• Recent EU Clinical Trials: A proof of concept and assessment of maximal effect study with low dose Fenfluramine as add-on therapy in Myoclonic Astatic Epilepsy (Doose-Syndrome)
• Description: Flufenamic acid (FFA), namely N-(alpha,alpha,alpha-trifluorom-tolyl) anthranilic acid (CI-440), is an aromatic amino acid consisting of anthranilic acid carrying an N-(trifluoromethyl)phenyl substituent. It is an effective drug in the treatment of special types of migraine. Its anti-inflammatory and analgesic effects were recognized in the 1960s (Winder et al., 1963) and thus FFA is included in the family of non-steroidal anti-inflammatory drugs (NSAIDs) with mefenamic, meclofenamic (MFA) and niflumic acids (NA). Anti-inflammatory actions occur mainly through reduction of prostaglandin synthesis from arachidonic acid by inhibiting the cyclo-oxygenases.
• Uses: Flufenamic acid is used for moderate pain and dysmenorrhea, but it should not be used for more than 1 week due to the possibility of nephrotoxicity, gastrointestinal toxicity, and anemia. It is frequently used in combination with the anticoagulant warfarin, the effect of which is strengthened when combined with flufenamic acid. An NSAID found to be a reversible gap junction blocker
• Therapeutic Function: Antiinflammatory, Antirheumatic

Technology Process of Flufenamic acid

There total 20 articles about Flufenamic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-(3-trifluoromethyl-phenylamino)-benzoic acid (diethylcarbamoylmethyl-methyl-carbamoyloxy)-methyl ester → sarcosine diethylamide (44897-15-6) + flufenamic acid (530-78-9)

Guidance literature:

With human plasma; In phosphate buffer; at 37 ℃; pH=7.4;

DOI:10.1002/ardp.200600145

Reference yield: 100.0%

2-(3-trifluoromethyl-phenylamino)-benzoic acid diethylcarbamoylmethylcarbamoyloxymethyl ester → 2-amino-N,N-diethylacetamide (34105-57-2) + flufenamic acid (530-78-9)

Guidance literature:

With human plasma; In phosphate buffer; at 37 ℃; pH=7.4;

DOI:10.1002/ardp.200600145

Reference yield: 100.0%

2-diethylcarbamoyl-pyrrolidine-1-carboxylic acid 2-(3-trifluoromethyl-phenylamino)-benzoyloxymethyl ester → flufenamic acid (530-78-9) + (2S)-N',N'-diethylpyrrolidinecarboxamide (41721-01-1,1018331-52-6,681032-78-0)

Guidance literature:

With human plasma; In phosphate buffer; at 37 ℃; pH=7.4;

DOI:10.1002/ardp.200600145

upstream raw materials:

2-Iodobenzoic acid

3-trifluoromethylaniline

ortho-chlorobenzoic acid

1-(3'-trifluoromethyl-phenyl)-1,2-dihydro-3,1-benzoxazin-4-one

Downstream raw materials:

N-(3-trifluoromethyl-phenyl)-anthranilic acid-(4-nitro-benzyl ester)

2-[[3-(trifluoromethyl)phenyl]amino]benzoic acid,methyl ester

2-(3-Trifluoromethyl-phenylamino)-benzoic acid 2-ethoxy-ethyl ester

2-(3-Trifluoromethyl-phenylamino)-benzoic acid benzoyloxymethyl ester

Refernces

• 1、 Deng, Jiedan,Hao, Xiangyong,Lei, Fang,Liang, Ziyi,Wang, Yuqing,Wang, Zhen,Yang, Xiaoyan,Zhang, Honghua. "Design, synthesis and bioactivity evaluation of novel N-phenyl-substituted evodiamine derivatives as potent anti-tumor agents". . . Retrieved 2022/01/10.
• 2、 Mélin, Léa,Abdullayev, Shuay,Fnaiche, Ahmed,Vu, Victoria,González Suárez, Narjara,Zeng, Hong,Szewczyk, Magdalena M.,Li, Fengling,Senisterra, Guillermo,Allali-Hassani, Abdellah,Chau, Irene,Dong, Aiping,Woo, Simon,Annabi, Borhane,Halabelian, Levon,LaPlante, Steven R.,Vedadi, Masoud,Barsyte-Lovejoy, Dalia,Santhakumar, Vijayaratnam,Gagnon, Alexandre. "Development of LM98, a Small-Molecule TEAD Inhibitor Derived from Flufenamic Acid". . p. 2982 - 3002. Retrieved 2021/08/03.