Flufenamic acid

Flufenamic acid
Clinical data
AHFS/Drugs.com International Drug Names
Routes of
administration		 oral, topical
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
Pharmacokinetic data
Protein binding extensively
Metabolism Hydroxylation, glucuronidation
Elimination half-life ~3 h
Excretion 50% urine, 36% feces
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.007.723 Edit this at Wikidata
Chemical and physical data
Formula C14H10F3NO2
Molar mass 281.22991 g/mol
3D model (JSmol)
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)
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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. 1 2 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. 1 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



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