Flufenamic acid

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Flufenamic acid
Flufenamic acid.png
Flufenamic acid-3D-balls.png
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
  • 530-78-9 ☑Y
PubChem CID
  • 3371
IUPHAR/BPS
  • 2447
DrugBank
  • DB02266 ☑Y
ChemSpider
  • 3254 ☑Y
UNII
  • 60GCX7Y6BH
KEGG
  • D01581 ☑Y
ChEBI
  • CHEBI:42638 ☑Y
ChEMBL
  • CHEMBL23588 ☑Y
ECHA InfoCard 100.007.723
Chemical and physical data
Formula C14H10F3NO2
Molar mass 281.22991 g/mol
3D model (JSmol)
  • 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)
  (verify)

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. ^ a b 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. ^ a b 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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