Meclofenamic acid

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Meclofenamic acid
File:Meclofenamic acid.png
Systematic (IUPAC) name
2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid
Clinical data
Trade names Meclomen
AHFS/Drugs.com International Drug Names
Routes of
administration		 Oral
Identifiers
CAS Number 644-62-2
ATC code M01AG04 (WHO) M02AA18
PubChem CID: 4037
IUPHAR/BPS 7219
DrugBank DB00939
ChemSpider 3897
UNII 48I5LU4ZWD YesY
KEGG D02341
ChEBI CHEBI:6710
ChEMBL CHEMBL509 YesY
Chemical data
Formula C14H11Cl2NO2
Molecular mass 296.14864 g/mol

Meclofenamic acid (meclofenamate sodium, brand Meclomen) is a drug used for joint, muscular pain, arthritis and dysmenorrhea.[1] It is a member of the anthranilic acid derivatives (or fenamate) class of NSAID drugs and was approved by the FDA in 1980.[2] Like other members of the class, it is a COX inhibitor and prevents formation of prostaglandins.[3]

Scientists led by Claude Winder from Parke-Davis invented meclofenamate sodium in 1964, along with fellow members of the class, mefenamic acid in 1961 and flufenamic acid in 1963.[4]:718

Patents on the drug expired in 1985[5]:295 and several generics were introduced in the US, but as of July 2015 only Mylan still sold it.[6][7]

It is not widely used in humans as it a high rate (30-60%) rate of gastrointestinal side effects.[8]:310

Use in horses

Meclofenamic acid is sold under the trade name "Arquel" for use in horses, and is administered as an oral granual form at a dose of 2.2 mg/kg/day.[9] It has a relatively slow onset of action, taking 36–48 hours for full effect,[10] and is most useful for treatment of chronic musculoskeletal disease.[11] It has been found to be beneficial for the treatment of navicular syndrome, laminitis, and osteoarthritis,[10] in some cases having a more profound effect than the commonly-used NSAID phenylbutazone.[12] However, due to cost, it is not routinely used in practice. Toxicity due to excessive dosage is similar to that of phenylbutazone, including depression, anorexia, weight loss, edema, diarrhea, oral ulceration, and decreased hematocrit.[12]

References

  1. ↑ http://www.medicinenet.com/meclofenamate/article.htm
  2. ↑ FDA Meclomen page at FDA Page accessed July 3, 2015
  3. ↑ NIH LiverTox Database Mefenamic Acid Last updated June 23, 2015. Page accessed July 3, 2015
  4. ↑ Whitehouse M. Drugs to Treat Inflammation: A Historical Overview. pp 707-729 in Frontiers in Medicinal Chemistry , Volume 4. Eds Rahman A, et al. Bentham Science Publishers, 2009 ISBN 9781608052073
  5. ↑ United States. Congress. Office of Technology Assessment Pharmaceutical R & D: Costs, Risks & Rewards DIANE Publishing, 1993 ISBN 9780788104688
  6. ↑ FDA Meclofenamate sodium ANDAs at FDA Page accessed July 3, 2015
  7. ↑ FDA Mylan label for meclofenamate sodium Revised: October 2013, Accessed July 3, 2015
  8. ↑ Jeffrey K. Aronson. Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs. Elsevier, 2009 ISBN 9780080932941
  9. ↑ McIlwraith CW, Frisbie DD, Kawcak CE. Nonsteroidal Anti-Inflammatory Drugs. Proc. AAEP 2001 (47): 182-187.
  10. ↑ 10.0 10.1 Cotter GH, Riley WF, Beck CC, Coppock RW. Arquel (Cl- 1583). A new nonsteroidal anti-inflammatory drug for horses, in Proceedings. Am Assoc Equine Practnr 1973;19: 81–90.
  11. ↑ Snow DH, Baxter P, Whiting B. The pharmacokinetics of meclofenamic acid in the horse. J Vet Pharmacol Ther 1981; 4:147–156.
  12. ↑ 12.0 12.1 Lees P, Higgins AJ. Clinical pharmacology in therapeutic uses of non-steroidal anti-inflammatory drugs in the horse. Equine Vet J 1985;17:83–96.
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