Tolfenamic acid
Non-steroidal anti-inflammatory drug
- M01AG02 (WHO)
- AU: S4 (Prescription only)
- 2-[(3-chloro-2-methylphenyl)amino]benzoic acid)[1]
- 13710-19-5
N
- 610479
- 530683
Y
- 3G943U18KM
- D01183 Y
- CHEBI:32243 N
- ChEMBL121626 Y
- DTXSID1045409
- Interactive image
- 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-NY
N
Y (what is this?) (verify)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]
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]
Structure
Tolfenamic acid (TFA), 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.[6]
Currently, nine forms of TFA have been identified, some of which are determined by conformational states. [7][8][9] 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.ref name = "Case_2018" /> This diversity in solid forms makes TFA an attractive candidate for modification and utilization in medical applications.
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.[10][11] However, despite its efficacy when administered intramuscularly, subcutaneously, or orally,[12] 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.[13][14]
Nevertheless, TFA exhibits promise in medical practice, demonstrating the ability to inhibit the growth of cancer cells in the pancreas, sigmoid colon, and rectum.[15] Further research and development may unveil its potential for therapeutic applications in the future.
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.
- ^ 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
- ^ Drugs.com Drugs.com international listings for tolfenamic acid Page accessed July 3, 2015
- ^ 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.
- ^ 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.
- ^ 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.
External links
- Tolfenamic acid information (Diseases Database)
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