Flufenamic acid
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| Systematic (IUPAC) name | |
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2-{[3-(Trifluoromethyl)phenyl]amino}benzoic acid
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| Clinical data | |
| AHFS/Drugs.com | International Drug Names |
| Legal status |
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| Routes of administration |
oral, topical |
| Pharmacokinetic data | |
| Protein binding | extensively |
| Metabolism | Hydroxylation, glucuronidation |
| Biological half-life | ~3 h |
| Excretion | 50% urine, 36% feces |
| Identifiers | |
| CAS Number | 530-78-9  Y |
| ATC code | M01AG03 (WHO) |
| PubChem | CID: 3371 |
| IUPHAR/BPS | 2447 |
| DrugBank | DB02266 Y |
| ChemSpider | 3254 Y |
| UNII | 60GCX7Y6BH Y |
| KEGG | D01581 Y |
| ChEBI | CHEBI:42638 Y |
| ChEMBL | CHEMBL23588 Y |
| Chemical data | |
| Formula | C14H10F3NO2 |
| Molecular mass | 281.22991 g/mol |
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| Physical data | |
| 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
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| Propionic acid derivatives (profens) |
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| N-Arylanthranilic acids (fenamates) |
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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 #WHO-EM †Withdrawn drugs.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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Prostanoid signaling
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See also: Leukotrienergics
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- ↑ 1.0 1.1 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
- ↑ 2.0 2.1 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)"
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ 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
