Flufenamic acid
{{Drugbox
| Watchedfields = changed
| verifiedrevid = 443821617
| IUPAC_name = 2-{[3-(Trifluoromethyl)phenyl]amino}benzoic acid
| image = flufenamic acid.png
| image2 = Flufenamic acid-3D-balls.png
| tradename =
| Drugs.com = International Drug Names
| pregnancy_AU =
| pregnancy_US =
| pregnancy_category =
| legal_AU = S4
| legal_CA =
| legal_UK =
| legal_US =
| legal_status =
| routes_of_administration = oral, 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
| molecular_weight = 281.22991 g/mol
| smiles = FC(F)(F)c1cc(ccc1)Nc2ccccc2C(=O)O
| InChI = 1/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)
| InChIKey = LPEPZBJOKDYZAD-UHFFFAOYAI
| 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 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
- ^ 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 | |
|---|---|
| salicylates | |
| acetic acid derivatives and related substances | |
| oxicams | |
| propionic acid derivatives (profens) |
|
| n-arylanthranilic acids (fenamates) | |
| COX-2 inhibitors (coxibs) | |
| other | |
| NSAID combinations | |
Key: underline indicates initially developed first-in-class compound of specific group; #WHO-Essential Medicines; †withdrawn drugs; ‡veterinary use. | |
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