Flufenamic acid

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Chemical compound

title: "Flufenamic acid" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["3-(trifluoromethyl)phenyl-compounds", "anthranilic-acids", "gabaa-receptor-positive-allosteric-modulators", "nmda-receptor-antagonists", "secondary-amines"] description: "Chemical compound" topic_path: "general/3-trifluoromethyl-phenyl-compounds" source: "https://en.wikipedia.org/wiki/Flufenamic_acid" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Watchedfields = changed | verifiedrevid = 443821617 | IUPAC_name = 2-{[3-(Trifluoromethyl)phenyl]amino}benzoic acid | image = flufenamic acid.png | image_class = skin-invert-image | image2 = Flufenamic acid-3D-balls.png | image_class2 = bg-transparent | tradename = | Drugs.com = | pregnancy_AU = | pregnancy_category = | legal_AU = S4 | legal_CA = | legal_UK = | legal_US = | legal_status = | routes_of_administration = By mouth, topical | bioavailability = | protein_bound = extensively | metabolism = Hydroxylation, glucuronidation | elimination_half-life = ~3 h | excretion = 50% urine, 36% feces | CAS_number_Ref = | CAS_number = 530-78-9 | ATC_prefix = M01 | ATC_suffix = AG03 | PubChem = 3371 | IUPHAR_ligand = 2447 | DrugBank_Ref = | DrugBank = DB02266 | ChemSpiderID_Ref = | ChemSpiderID = 3254 | UNII_Ref = | UNII = 60GCX7Y6BH | KEGG_Ref = | KEGG = D01581 | ChEBI_Ref = | ChEBI = 42638 | ChEMBL_Ref = | ChEMBL = 23588 | C=14 | H=10 | F=3 | N=1 | O=2 | smiles = FC(F)(F)c1cc(ccc1)Nc2ccccc2C(=O)O | StdInChI_Ref = | StdInChI = 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) | StdInChIKey_Ref = | StdInChIKey = LPEPZBJOKDYZAD-UHFFFAOYSA-N | melting_point = 124 | melting_high = 125 | melting_notes = resolidification and remelting at 134°C to 136°C | solubility = Practically insoluble in water; soluble in ethanol, chloroform and diethyl ether

Flufenamic acid (FFA) is a member of the anthranilic acid derivatives (or fenamate) class of nonsteroidal anti-inflammatory drugs (NSAIDs). FFA is known to bind to and reduce the activity of prostaglandin F synthase and activate TRPC6.

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.

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

Structure

Flufenamic acid is a highly polymorphic drug molecule with multiple structurally characterized polymorphic modifications. It has a unique chemical structure and stands out among fenamates. Nowadays, eight polymorphic forms are known that are determined by different conformers, which makes flufenamic acid unique among other low-molecular medicinal compounds. A fundamental feature of the structure of flufenamic acid, which has generated significant interest in the design and development of drugs, is the presence of a trifluoromethyl group. Compounds with fluorine-containing substituents are known to have promising chemical and biological properties, since such groups often improve the pharmacokinetics and bioavailability of drugs. Studies have shown the promise of repositioning flufenamic acid and the use of drugs based on it in the treatment of Bartter syndrome.

Medical uses

Until recently, FFA was actively used in medical practice as an analgesic with anti-inflammatory and antipyretic effects. FFA has been proven effective in treating rheumatoid arthritis, osteoarthritis and other inflammation-related diseases. However, despite this, the use of FFA in the United States and other countries is limited since the compound causes frequent side effects. The rate of gastrointestinal side effects can be as high as 60%, manifested as at least one of the following: dyspepsia, nausea, abdominal pain and discomfort, constipation, diarrhoea, flatulence, indigestion, epigastric distress, stomatitis and anorexia. Besides gastrointestinal side effects, the drug can cause headache, dizziness and peripheral oedema.

Side effects

It is not widely used in humans as it has a high rate (30–60%) of gastrointestinal side effects. It is generally not available in the US. It is available in some Asian and European countries as a generic drug.

References

References

  1. (23 June 2015). "Mefenamic Acid". U.S. National Institutes of Health (NIH).
  2. "Chemical–Gene Interaction Query: Flufenamic Acid (Homo sapiens)". North Carolina State University.
  3. (2005). "Drugs to treat inflammation: a historical introduction". Current Medicinal Chemistry.
  4. (June 3, 2015). "Application of the Method of Molecular Voronoi–Dirichlet Polyhedra for Analysis of Noncovalent Interactions in Crystal Structures of Flufenamic Acid—The Current Record-Holder of the Number of Structurally Studied Polymorphs". Crystal Growth & Design.
  5. (September 2020). "Tailor-Made Amino Acids and Fluorinated Motifs as Prominent Traits in Modern Pharmaceuticals". Chemistry: A European Journal.
  6. (February 2023). "Investigation of the Spatial Structure of Flufenamic Acid in Supercritical Carbon Dioxide Media via 2D NOESY". Materials.
  7. (June 2023). "Conformational State of Fenamates at the Membrane Interface: A MAS NOESY Study". Membranes.
  8. (December 2014). "Conformational origins of polymorphism in two forms of flufenamic acid". Journal of Molecular Structure.
  9. (June 2012). "Nonamorphism in flufenamic acid and a new record for a polymorphic compound with solved structures". Journal of the American Chemical Society.
  10. (April 2018). "Potent and selective aldo-keto reductase 1C3 (AKR1C3) inhibitors based on the benzoisoxazole moiety: application of a bioisosteric scaffold hopping approach to flufenamic acid". European Journal of Medicinal Chemistry.
  11. (July 2013). "Exploration of fluorine chemistry at the multidisciplinary interface of chemistry and biology". The Journal of Organic Chemistry.
  12. (November 2012). "Synthetic chemistry and biological activity of pentafluorosulphanyl (SF5) organic molecules". Journal of Fluorine Chemistry.
  13. (October 2015). "Pentafluorosulfanyl-containing flufenamic acid analogs: Syntheses, properties and biological activities". Bioorganic & Medicinal Chemistry Letters.
  14. (May 2017). "Pharmaceutical Co-Crystal of Flufenamic Acid: Synthesis and Characterization of Two Novel Drug-Drug Co-Crystal". Journal of Pharmaceutical Sciences.
  15. (February 2020). "The role of solid state properties on the dissolution performance of flufenamic acid". Journal of Pharmaceutical and Biomedical Analysis.
  16. (August 2022). "The Latest FDA-Approved Pharmaceuticals Containing Fragments of Tailor-Made Amino Acids and Fluorine". Pharmaceuticals.
  17. (2016). "Meyler's Side Effects of Drugs". Elsevier.
  18. Aronson, Jeffrey K.. (2009). "Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs". Elsevier.
  19. "International listings for flufenamic acid". Drugs.com.

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3-(trifluoromethyl)phenyl-compoundsanthranilic-acidsgabaa-receptor-positive-allosteric-modulatorsnmda-receptor-antagonistssecondary-amines