Meclofenamic acid (original) (raw)

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Chemical compound

Pharmaceutical compound

Meclofenamic acid
Clinical data
Trade names Meclomen
AHFS/Drugs.com International Drug Names
Routes of administration By mouth
ATC code M01AG04 (WHO) M02AA18 (WHO)
Identifiers
IUPAC name 2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid
CAS Number 644-62-2
PubChem CID 4037
IUPHAR/BPS 7219
DrugBank DB00939
ChemSpider 3897
UNII 48I5LU4ZWD
KEGG D02341
ChEBI CHEBI:6710
ChEMBL ChEMBL509 checkY
CompTox Dashboard (EPA) DTXSID0048559 Edit this at Wikidata
ECHA InfoCard 100.010.382 Edit this at Wikidata
Chemical and physical data
Formula C14H11Cl2NO2
Molar mass 296.15 g·mol−1

Meclofenamic acid (used as meclofenamate sodium, brand name 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 nonsteroidal anti-inflammatory drugs (NSAIDs) and was approved by the US FDA in 1980.[2] Like other members of the class, it is a cyclooxygenase (COX) inhibitor, preventing the 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 has a high rate (30-60%) rate of gastrointestinal side effects.[8]: 310

In October 2020, the U.S. Food and Drug Administration (FDA) required the drug label to be updated for all nonsteroidal anti-inflammatory medications to describe the risk of kidney problems in unborn babies that result in low amniotic fluid.[9][10] They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.[9][10]

Meclofenamic acid is sold under the trade name "Arquel" for use in horses, and is administered as an oral granule form at a dose of 2.2 mg/kg/day.[11] It has a relatively slow onset of action, taking 36–48 hours for full effect,[12] and is most useful for treatment of chronic musculoskeletal disease.[13] It has been found to be beneficial for the treatment of navicular syndrome, laminitis, and osteoarthritis,[12] in some cases having a more profound effect than the commonly used NSAID phenylbutazone.[14] 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.[14]

  1. ^ "meclofenamate, Meclomen: Drug Facts, Side Effects and Dosing". medicinenet.com.
  2. ^ FDA Meclomen page at FDA Page accessed July 3, 2015
  3. ^ "Mefenamic Acid". NIH LiverTox Database. June 23, 2015. PMID 31643176. Retrieved July 3, 2015.
  4. ^ Whitehouse M (2009). "Drugs to Treat Inflammation: A Historical Overview.". In Rahman A, et al. (eds.). Frontiers in Medicinal Chemistry. Vol. 4. Bentham Science Publishers. pp. 707–729. ISBN 978-1-60805-207-3.
  5. ^ United States. Congress. Office of Technology Assessment Pharmaceutical R & D: Costs, Risks & Rewards DIANE Publishing, 1993 ISBN 978-0-7881-0468-8
  6. ^ "Meclofenamate sodium ANDAs". U.S. Food and Drug Administration. Archived from the original on 4 June 2015. Retrieved 3 July 2015.
  7. ^ "Mylan label for meclofenamate sodium". Daily Med. U.S. Food and Drug Administration. October 2013. Retrieved 3 July 2015.
  8. ^ Aronson JK (2009). Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs. Elsevier. ISBN 978-0-08-093294-1.
  9. ^ a b "FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications". U.S. Food and Drug Administration (FDA) (Press release). 15 October 2020. Retrieved 15 October 2020. Public Domain This article incorporates text from this source, which is in the public domain.
  10. ^ a b "NSAIDs may cause rare kidney problems in unborn babies". U.S. Food and Drug Administration. 21 July 2017. Retrieved 15 October 2020. Public Domain This article incorporates text from this source, which is in the public domain.
  11. ^ McIlwraith CW, Frisbie DD, Kawcak CE (2001). "Nonsteroidal Anti-Inflammatory Drugs". Proc. AAEP. 47: 182–187.
  12. ^ a b Cotter GH, Riley WF, Beck CC, Coppock RW (1973). "Arquel (Cl- 1583). A new nonsteroidal anti-inflammatory drug for horses". Proceedings. Am Assoc Equine Practnr. 19: 81–90.
  13. ^ Snow DH, Baxter P, Whiting B (June 1981). "The pharmacokinetics of meclofenamic acid in the horse". Journal of Veterinary Pharmacology and Therapeutics. 4 (2): 147–56. doi:10.1111/j.1365-2885.1981.tb00724.x. PMID 7349327.
  14. ^ a b Lees P, Higgins AJ (March 1985). "Clinical pharmacology and therapeutic uses of non-steroidal anti-inflammatory drugs in the horse". Equine Veterinary Journal. 17 (2): 83–96. doi:10.1111/j.2042-3306.1985.tb02056.x. PMID 3987667.