Flufenamic acid

Flufenamic acid

Clinical data
AHFS/Drugs.com	International Drug Names
Routes of administration	oral, topical
ATC code	M01AG03 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)
Pharmacokinetic data
Protein binding	extensively
Metabolism	Hydroxylation, glucuronidation
Biological half-life	~3 h
Excretion	50% urine, 36% feces
Identifiers
IUPAC name 2-{[3-(Trifluoromethyl)phenyl]amino}benzoic acid
CAS Number	530-78-9
PubChem (CID)	3371
IUPHAR/BPS	2447
DrugBank	DB02266
ChemSpider	3254
UNII	60GCX7Y6BH
KEGG	D01581
ChEBI	CHEBI:42638
ChEMBL	CHEMBL23588
ECHA InfoCard	100.007.723
Chemical and physical data
Formula	C14H10F3NO2
Molar mass	281.22991 g/mol
3D model (Jmol)	Interactive image
Melting point	124 to 125 °C (255 to 257 °F) resolidification and remelting at 134°C to 136°C
Solubility in water	Practically insoluble in water; soluble in ethanol, chloroform and diethyl ether mg/mL (20 °C)
SMILES FC(F)(F)c1cc(ccc1)Nc2ccccc2C(=O)O
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) Key:LPEPZBJOKDYZAD-UHFFFAOYSA-N
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Flufenamic acid is a member of the anthranilic acid derivatives (or fenamate) class of NSAID drugs^[1]:718 Like other members of the class, it is a COX inhibitor and prevents formation of prostaglandins.^[2] Flufenamic acid is known to bind to and reduce the activity of prostaglandin F synthase and activate TRPC6.^[3]

It is not widely used in humans as it has a high rate (30-60%) of gastrointestinal side effects.^[4]:310 It is generally not available in the US.^[2] It is available in some Asian and European countries as a generic.^[5]

Scientists led by Claude Winder from Parke-Davis invented flufenamic acid in 1963, along with fellow members of the class, mefenamic acid in 1961 and meclofenamate sodium in 1964.^[1]:718

References

1. Whitehouse M. Drugs to Treat Inflammation: A Historical Overview. pp 707-729 in Frontiers in Medicinal Chemistry , Volume 4. Eds Rahman A, et al. Bentham Science Publishers, 2009 ISBN 9781608052073
2. NIH LiverTox Database Mefenamic Acid Last updated June 23, 2015. Page accessed July 3, 2015. Quote: "(fenamates generally not available in the United States, such as tolfenamic acid and flufenamic acid)"
3. "Chemical–Gene Interaction Query: Flufenamic Acid (Homo sapiens)". Comparative Toxicogenomics Database. North Carolina State University. Retrieved 4 July 2015.
4. Jeffrey K. Aronson. Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs. Elsevier, 2009 ISBN 9780080932941
5. Drugs.com Drugs.com international listings for flufenamic acid Page accessed July 3, 2015