Tolfenamic acid

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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
  • 2-[(3-chloro-2-methylphenyl)amino]benzoic acid)[1]
JSmol)
  • Clc2cccc(Nc1ccccc1C(=O)O)c2C
  • 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) checkY
  • Key:YEZNLOUZAIOMLT-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Tolfenamic acid (Clotam, Tufnil, TFA) is a member of the

prostaglandins.[3]

It is used in the UK as a treatment for migraine.[4][5] 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.[6]

Medical uses

TFA, like other non-steroidal anti-inflammatory drugs (NSAIDs), finds utility in the prevention and treatment of conditions associated with pain and inflammation.[7][8] However, despite its efficacy when administered intramuscularly, subcutaneously, or orally,[9] TFA-based drugs have not yet gained approval in the United States and some other countries due to the significant number of reported side effects.[10][11]

Nevertheless, TFA exhibits promise in medical practice, demonstrating the ability to inhibit the growth of cancer cells in the pancreas, sigmoid colon, and rectum.[12] Further research and development may unveil its potential for therapeutic applications in the future.

Chemistry

Tolfenamic acid, belonging to the pharmacological group of fenamates, possesses a chemical structure typical of anthranilic acid derivatives. In this structure, one of the hydrogen atoms of the nitro group is substituted by a benzene ring featuring a methyl group and a chlorine atom at the ortho- and meta- positions, respectively.[13]

Currently, nine forms of TFA have been identified, some of which are determined by conformational states.[14][15][16] These polymorphic forms exhibit variations in the spatial arrangement within the unit cell and in the values of the C-N(H)-C-C angle.[16] This diversity in solid forms makes TFA an attractive candidate for modification and utilization in medical applications.

History

It was discovered by scientists at Medica Pharmaceutical Company in Finland.[2]

References

  1. doi:10.1039/P29890001443
    .
  2. ^
    S2CID 9428076
    .
  3. ^ 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)"
  4. ^ NHS Tolfenamic Acid (Tolfenamic acid 200mg tablets) Page accessed July 3, 2015
  5. ^ "Virtual Medicinal Product (VMP) - Tolfenamic acid 200mg tablets - dm+d browser". dmd-browser.nhsbsa.nhs.uk. Retrieved 2024-04-23.
  6. ^ Drugs.com Drugs.com international listings for tolfenamic acid Page accessed July 3, 2015
  7. PMID 4572954
    .
  8. PMID 21196413
    .
  9. S2CID 51930602
    .
  10. S2CID 12334561
    .
  11. PMID 7816786
    .
  12. PMID 20664734
    .
  13. PMID 19334766
    .
  14. S2CID 252630985
    .
  15. ISSN 1528-7483
    .
  16. ^
    ISSN 1528-7483
    .

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Tolfenamic_acid&oldid=1220444840"