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'''Flufenamic acid''' is a member of the [[Nonsteroidal_anti-inflammatory_drug#Anthranilic_acid_derivatives_.28Fenamates.29|anthranilic acid derivatives]] (or fenamate) class of [[NSAID]] drugs<ref name=Whitehouse/>{{rp|718}} Like other members of the class, it is a [[COX]] inhibitor and prevents formation of [[prostaglandins]].<ref name=LiverTox/> Flufenamic acid is known to bind to and reduce the activity of [[AKR1C3|prostaglandin F synthase]] and activate [[TRPC6]].<ref>{{cite web | title=Chemical–Gene Interaction Query: Flufenamic Acid (Homo sapiens) | url=http://ctdbase.org/query.go?type=ixn&chemqt=equals&chem=name%3AFlufenamic+Acid&actionDegreeTypes=increases&actionDegreeTypes=decreases&actionDegreeTypes=affects&actionTypes=activity&actionTypes=binding&geneqt=equals&gene=&pathwayqt=equals&pathway=&taxonqt=equals&taxon=TAXON%3A9606&goqt=equals&go=&sort=chemNmSort&perPage=500&action=Search|website=Comparative Toxicogenomics Database | publisher=North Carolina State University | accessdate=4 July 2015}}</ref>
'''Flufenamic acid''' ('''FFA''') is a member of the [[Nonsteroidal_anti-inflammatory_drug#Anthranilic_acid_derivatives_.28Fenamates.29|anthranilic acid derivatives]] (or fenamate) class of [[NSAID]] drugs<ref name=Whitehouse/>{{rp|718}} Like other members of the class, it is a [[COX]] inhibitor and prevents formation of [[prostaglandins]].<ref name=LiverTox/> FFA is known to bind to and reduce the activity of [[AKR1C3|prostaglandin F synthase]] and activate [[TRPC6]].<ref>{{cite web | title=Chemical–Gene Interaction Query: Flufenamic Acid (Homo sapiens) | url=http://ctdbase.org/query.go?type=ixn&chemqt=equals&chem=name%3AFlufenamic+Acid&actionDegreeTypes=increases&actionDegreeTypes=decreases&actionDegreeTypes=affects&actionTypes=activity&actionTypes=binding&geneqt=equals&gene=&pathwayqt=equals&pathway=&taxonqt=equals&taxon=TAXON%3A9606&goqt=equals&go=&sort=chemNmSort&perPage=500&action=Search|website=Comparative Toxicogenomics Database | publisher=North Carolina State University | accessdate=4 July 2015}}</ref>


It is not widely used in humans as it has a high rate (30-60%) of gastrointestinal side effects.<ref>Jeffrey K. Aronson. Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs. Elsevier, 2009 {{ISBN|9780080932941}}</ref>{{rp|310}} It is generally not available in the US.<ref name=LiverTox>NIH LiverTox Database [http://livertox.nih.gov/MefenamicAcid.htm 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)"</ref> It is available in some Asian and European countries as a generic.<ref>Drugs.com [https://www.drugs.com/international/flufenamic-acid.html Drugs.com international listings for flufenamic acid] Page accessed July 3, 2015</ref>
It is not widely used in humans as it has a high rate (30-60%) of gastrointestinal side effects.<ref>Jeffrey K. Aronson. Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs. Elsevier, 2009 {{ISBN|9780080932941}}</ref>{{rp|310}} It is generally not available in the US.<ref name=LiverTox>NIH LiverTox Database [http://livertox.nih.gov/MefenamicAcid.htm 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)"</ref> It is available in some Asian and European countries as a generic.<ref>Drugs.com [https://www.drugs.com/international/flufenamic-acid.html Drugs.com international listings for flufenamic acid] Page accessed July 3, 2015</ref>


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.<ref name=Whitehouse>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}}</ref>{{rp|718}}
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.<ref name=Whitehouse>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}}</ref>{{rp|718}}
==See also==
==See also==
*[[Flufenerim]], [[Flufenoxuron]] & [[Flufenisal]] all have the same prefix (Flufen).
*[[Flufenerim]], [[Flufenoxuron]] & [[Flufenisal]] all have the same prefix (Flufen).

Revision as of 09:28, 22 June 2019

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
  • 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 Edit this at Wikidata
Chemical and physical data
FormulaC14H10F3NO2
Molar mass281.22991 g/mol 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)
  • FC(F)(F)c1cc(ccc1)Nc2ccccc2C(=O)O
  • 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) checkY
  • Key:LPEPZBJOKDYZAD-UHFFFAOYSA-N checkY
  (verify)

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]

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 

See also

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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