Tolfenamic acid
Non-steroidal anti-inflammatory drug
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
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
^ 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 .
^ 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 .
^ 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)"
^ NHS Tolfenamic Acid (Tolfenamic acid 200mg tablets) Page accessed July 3, 2015
^ "Virtual Medicinal Product (VMP) - Tolfenamic acid 200mg tablets - dm+d browser" . dmd-browser.nhsbsa.nhs.uk . Retrieved 2024-04-23 .
^ Drugs.com Drugs.com international listings for tolfenamic acid Page accessed July 3, 2015
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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 .
^ 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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Sodium
VGSCs Tooltip Voltage-gated sodium channels
ENaC Tooltip Epithelial sodium channel
ASICs Tooltip Acid-sensing ion channel
Chloride
CaCCs Tooltip Calcium-activated chloride channel
CFTR Tooltip Cystic fibrosis transmembrane conductance regulator
Unsorted
Others
TRPs Tooltip Transient receptor potential channels LGICs Tooltip Ligand gated ion channels