Flufenamic acid

Flufenamic acid (FFA) is a member of the anthranilic acid derivatives (or fenamate) class of nonsteroidal anti-inflammatory drugs (NSAIDs).[1]: 718  Like other members of the class, it is a cyclooxygenase (COX) inhibitor, preventing the 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		By mouth, 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
IUPAC name
  • 2-{[3-(Trifluoromethyl)phenyl]amino}benzoic acid
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)
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) Y
  • Key:LPEPZBJOKDYZAD-UHFFFAOYSA-N Y
  (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 drug.[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 meclofenamic acid in 1964.[1]: 718 

Although flufenamic acid was at one time informally referred to as "Fluffy" (see history cache), this pet name could also refer to flufenoxine.

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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