Flufenamic acid
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Clinical data | |
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AHFS/Drugs.com | International Drug Names |
Routes of administration |
oral, topical |
ATC code | M01AG03 (WHO) |
Legal status | |
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Pharmacokinetic data | |
Protein binding | extensively |
Metabolism | Hydroxylation, glucuronidation |
Biological half-life | ~3 h |
Excretion | 50% urine, 36% feces |
Identifiers | |
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CAS Number | 530-78-9 ![]() |
PubChem (CID) | 3371 |
IUPHAR/BPS | 2447 |
DrugBank | DB02266 ![]() |
ChemSpider | 3254 ![]() |
UNII | 60GCX7Y6BH ![]() |
KEGG | D01581 ![]() |
ChEBI | CHEBI:42638 ![]() |
ChEMBL | CHEMBL23588 ![]() |
ECHA InfoCard | 100.007.723 |
Chemical and physical data | |
Formula | C14H10F3NO2 |
Molar mass | 281.22991 g/mol |
3D model (Jmol) | 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) |
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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[edit]
- ^ 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
- ^ 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)"
- ^ "Chemical–Gene Interaction Query: Flufenamic Acid (Homo sapiens)". Comparative Toxicogenomics Database. North Carolina State University. Retrieved 4 July 2015.
- ^ Jeffrey K. Aronson. Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs. Elsevier, 2009 ISBN 9780080932941
- ^ Drugs.com Drugs.com international listings for flufenamic acid Page accessed July 3, 2015
Pyrazolones / Pyrazolidines |
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Salicylates | |
Acetic acid derivatives and related substances |
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Oxicams | |
Propionic acid derivatives (profens) |
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N-Arylanthranilic acids (fenamates) |
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Coxibs | |
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Items listed in bold indicate initially developed compounds of specific groups. #WHO-EM †Withdrawn drugs. ‡Veterinary use medications.
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See also: Leukotrienergics
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