Tolfenamic acid

Tolfenamic acid (Clotam, Tufnil) is a member of the anthranilic acid derivatives (or fenamate) class of NSAID drugs discovered by scientists at Medica Pharmaceutical Company in Finland.[2] Like other members of the class, it is a COX inhibitor and prevents formation of prostaglandins.[3]

Tolfenamic acid
Clinical data
Trade namesClotam, Clotan, Tufnil
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
Identifiers
IUPAC name
  • 2-[(3-chloro-2-methylphenyl)amino]benzoic acid)[1]
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.033.862
Chemical and physical data
FormulaC14H12ClNO2
Molar mass261.71 g·mol−1
3D model (JSmol)
SMILES
  • Clc2cccc(Nc1ccccc1C(=O)O)c2C
InChI
  • InChI=1S/C14H12ClNO2/c1-9-11(15)6-4-8-12(9)16-13-7-3-2-5-10(13)14(17)18/h2-8,16H,1H3,(H,17,18) Y
  • Key:YEZNLOUZAIOMLT-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

It is used in the UK as a treatment for migraine.[4] It is generally not available in the US.[3] It is available in some Asian, Latin American and European countries as a generic drug for humans and for animals.[5]

References
  1. Andersen KV, Larsen S, Alhede B, Gelting N, Buchardt O (1989). "Characterization of two polymorphic forms of tolfenamic acid, N-(2-methyl-3-chlorophenyl)anthranilic acid: their crystal structures and relative stabilities". J. Chem. Soc., Perkin Trans. 2 (10): 1443–1447. doi:10.1039/P29890001443.
  2. Pentikäinen PJ, Neuvonen PJ, Backman C (1981). "Human pharmacokinetics of tolfenamic acid, a new anti-inflammatory agent". European Journal of Clinical Pharmacology. 19 (5): 359–65. doi:10.1007/bf00544587. PMID 7238564. S2CID 9428076.
  3. 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)"
  4. NHS Tolfenamic Acid (Tolfenamic acid 200mg tablets) Page accessed July 3, 2015
  5. Drugs.com Drugs.com international listings for tolfenamic acid Page accessed July 3, 2015
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