Flufenamic acid

Flufenamic acid (FFA) 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] FFA is known to bind to and reduce the activity of prostaglandin F synthase and activate TRPC6.[3]

Flufenamic acid
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		oral, topical
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
Pharmacokinetic data
Protein bindingextensively
MetabolismHydroxylation, glucuronidation
Elimination half-life~3 h
Excretion50% urine, 36% feces
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.007.723
Chemical and physical data
FormulaC14H10F3NO2
Molar mass281.234 g·mol−1
3D model (JSmol)
Melting point124 to 125 °C (255 to 257 °F) resolidification and remelting at 134°C to 136°C
Solubility in waterPractically insoluble in water; soluble in ethanol, chloroform and diethyl ether mg/mL (20 °C)
  (verify)

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 FFA in 1963, along with fellow members of the class, mefenamic acid in 1961 and meclofenamate sodium in 1964.[1]:718

References
  1. Whitehouse MW (2005). "Drugs to treat inflammation: a historical introduction". Current Medicinal Chemistry. 12 (25): 2931–42. doi:10.2174/092986705774462879. ISBN 9781608052073. PMID 16378496.
  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. Aronson JK (2009). Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs. Elsevier. ISBN 978-0-08-093294-1.
  5. "International listings for flufenamic acid". Drugs.com. Retrieved 3 July 2015.



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