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Tolfenamic acid

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Tolfenamic acid
Clinical data
Trade namesClotam, Clotan, Tufnil, Migea
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]
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.033.862 Edit this at Wikidata
Chemical and physical data
FormulaC14H12ClNO2
Molar mass261.71 g·mol−1
3D model (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 anthranilic acid derivatives (or fenamate) class of NSAID drugs.[2] Like other members of the class, it is a COX inhibitor and prevents formation of 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

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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

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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

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

References

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  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. ^ a b Pentikäinen PJ, Neuvonen PJ, Backman C (1981). "Human pharmacokinetics of tolfenamic acid, a new anti-inflammatory agent". European Journal of Clinical Pharmacology. 19 (5): 359–365. doi:10.1007/bf00544587. PMID 7238564. 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. ^ Kajander A, Laine V, Gothoni G (January 1972). "Effect of tolfenamic acid in rheumatoid arthritis". Scandinavian Journal of Rheumatology. 1 (2): 91–93. doi:10.3109/03009747209103003. PMID 4572954.
  8. ^ Basha R, Baker CH, Sankpal UT, Ahmad S, Safe S, Abbruzzese JL, et al. (January 2011). "Therapeutic applications of NSAIDS in cancer: special emphasis on tolfenamic acid". Frontiers in Bioscience. 3 (2): 797–805. doi:10.2741/s188. PMID 21196413.
  9. ^ Corum O, Corum DD, Er A, Yildiz R, Uney K (December 2018). "Pharmacokinetics and bioavailability of tolfenamic acid in sheep". Journal of Veterinary Pharmacology and Therapeutics. 41 (6): 871–877. doi:10.1111/jvp.12702. PMID 30084126. S2CID 51930602.
  10. ^ Kjaersgård Rasmussen MJ, Holt Larsen B, Borg L, Soelberg Sørensen P, Hansen PE (June 1994). "Tolfenamic acid versus propranolol in the prophylactic treatment of migraine". Acta Neurologica Scandinavica. 89 (6): 446–450. doi:10.1111/j.1600-0404.1994.tb02664.x. PMID 7976233. S2CID 12334561.
  11. ^ Isomäki H (October 1994). "Tolfenamic acid: clinical experience in rheumatic diseases". Pharmacology & Toxicology. 75 (s2): 64–65. doi:10.1111/j.1600-0773.1994.tb02001.x. PMID 7816786.
  12. ^ Kim JH, Jung JY, Shim JH, Kim J, Choi KH, Shin JA, et al. (July 2010). "Apoptotic Effect of Tolfenamic Acid in KB Human Oral Cancer Cells: Possible Involvement of the p38 MAPK Pathway". Journal of Clinical Biochemistry and Nutrition. 47 (1): 74–80. doi:10.3164/jcbn.10-02. PMC 2901767. PMID 20664734.
  13. ^ López-Mejías V, Kampf JW, Matzger AJ (April 2009). "Polymer-induced heteronucleation of tolfenamic acid: structural investigation of a pentamorph". Journal of the American Chemical Society. 131 (13): 4554–4555. doi:10.1021/ja806289a. PMC 2729806. PMID 19334766.
  14. ^ Belov KV, Dyshin AA, Krestyaninov MA, Efimov SV, Khodov IA, Kiselev MG (December 2022). "Conformational preferences of tolfenamic acid in DMSO-CO2 solvent system by 2D NOESY". Journal of Molecular Liquids. 367: 120481. doi:10.1016/j.molliq.2022.120481. S2CID 252630985.
  15. ^ SeethaLekshmi S, Guru Row TN (2012-08-01). "Conformational Polymorphism in a Non-steroidal Anti-inflammatory Drug, Mefenamic Acid". Crystal Growth & Design. 12 (8): 4283–4289. doi:10.1021/cg300812v. ISSN 1528-7483.
  16. ^ a b Case DH, Srirambhatla VK, Guo R, Watson RE, Price LS, Polyzois H, et al. (2018-09-05). "Successful Computationally Directed Templating of Metastable Pharmaceutical Polymorphs". Crystal Growth & Design. 18 (9): 5322–5331. doi:10.1021/acs.cgd.8b00765. ISSN 1528-7483.
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