Chemistry:Meclofenamic acid

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Short description: Chemical compound
Meclofenamic acid
Meclofenamic acid.png
Clinical data
Trade namesMeclomen
AHFS/Drugs.comInternational Drug Names
Routes of
administration		By mouth
ATC code
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC14H11Cl2NO2
Molar mass296.15 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

Adverse effects

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]

Use in horses

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]

References

  1. ↑ "meclofenamate, Meclomen: Drug Facts, Side Effects and Dosing". http://www.medicinenet.com/meclofenamate/article.htm. 
  2. ↑ FDA Meclomen page at FDA Page accessed July 3, 2015
  3. ↑ "Mefenamic Acid". NIH LiverTox Database. June 23, 2015. PMID 31643176. http://livertox.nih.gov/MefenamicAcid.htm. Retrieved July 3, 2015. 
  4. ↑ "Drugs to Treat Inflammation: A Historical Overview.". Frontiers in Medicinal Chemistry. 4. Bentham Science Publishers. 2009. 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. http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=MECLOFENAMATE%20SODIUM. 
  7. ↑ "Mylan label for meclofenamate sodium". Daily Med. U.S. Food and Drug Administration. October 2013. http://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=96f19af4-de8f-4fd7-90d8-55fe6ebdd81d&type=display. 
  8. ↑ Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs. Elsevier. 2009. ISBN 978-0-08-093294-1. 
  9. ↑ 9.0 9.1 "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. This article incorporates text from this source, which is in the public domain.
  10. ↑ 10.0 10.1 "NSAIDs may cause rare kidney problems in unborn babies". 21 July 2017. https://www.fda.gov/drugs/drug-safety-and-availability/fda-recommends-avoiding-use-nsaids-pregnancy-20-weeks-or-later-because-they-can-result-low-amniotic.  This article incorporates text from this source, which is in the public domain.
  11. ↑ "Nonsteroidal Anti-Inflammatory Drugs.". Proc. AAEP 47: 182–187. 2001. 
  12. ↑ 12.0 12.1 "Arquel (Cl- 1583). A new nonsteroidal anti-inflammatory drug for horses". Proceedings. Am Assoc Equine Practnr 19: 81–90. 1973. 
  13. ↑ "The pharmacokinetics of meclofenamic acid in the horse". Journal of Veterinary Pharmacology and Therapeutics 4 (2): 147–56. June 1981. doi:10.1111/j.1365-2885.1981.tb00724.x. PMID 7349327. 
  14. ↑ 14.0 14.1 "Clinical pharmacology and therapeutic uses of non-steroidal anti-inflammatory drugs in the horse". Equine Veterinary Journal 17 (2): 83–96. March 1985. doi:10.1111/j.2042-3306.1985.tb02056.x. PMID 3987667. 



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