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Meclofenamic acid

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Meclofenamic acid
Clinical data
Trade namesMeclomen
AHFS/Drugs.comInternational Drug Names
Routes of
administration
By mouth
ATC code
Identifiers
  • 2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.010.382Edit this at Wikidata
Chemical and physical data
FormulaC14H11Cl2NO2
Molar mass296.15 g·mol−1

Meclofenamic acid (used asmeclofenamate sodium, brand nameMeclomen) is a drug used for joint, muscular pain, arthritis anddysmenorrhea.[1]It is a member of theanthranilic acid derivatives (or fenamate) class ofnonsteroidal anti-inflammatory drugs (NSAIDs) and was approved by the USFDA in 1980.[2] Like other members of the class, it is acyclooxygenase (COX) inhibitor, preventing the formation ofprostaglandins.[3]

Scientists led by Claude Winder fromParke-Davis invented meclofenamate sodium in 1964, along with fellow members of the class,mefenamic acid in 1961 andflufenamic 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 onlyMylan 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

[edit]

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

Use in horses

[edit]

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 ofnavicular syndrome,laminitis, andosteoarthritis,[12] in some cases having a more profound effect than the commonly used NSAIDphenylbutazone.[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 decreasedhematocrit.[14]

References

[edit]
  1. ^"meclofenamate, Meclomen: Drug Facts, Side Effects and Dosing".medicinenet.com.
  2. ^FDAMeclomen page at FDA[dead link] Page accessed July 3, 2015
  3. ^"Mefenamic Acid".NIH LiverTox Database. June 23, 2015.PMID 31643176. Archived fromthe original on February 18, 2013. RetrievedJuly 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 AssessmentPharmaceutical R & D: Costs, Risks & Rewards DIANE Publishing, 1993ISBN 978-0-7881-0468-8
  6. ^"Meclofenamate sodium ANDAs". U.S. Food and Drug Administration. Archived fromthe original on 4 June 2015. Retrieved3 July 2015.
  7. ^"Mylan label for meclofenamate sodium".Daily Med. U.S. Food and Drug Administration. October 2013. Retrieved3 July 2015.
  8. ^Aronson JK (2009).Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs. Elsevier.ISBN 978-0-08-093294-1.
  9. ^ab"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. Archived fromthe original on October 16, 2020. Retrieved15 October 2020.Public Domain This article incorporates text from this source, which is in thepublic domain.
  10. ^ab"NSAIDs may cause rare kidney problems in unborn babies".U.S. Food and Drug Administration. 21 July 2017. Archived fromthe original on October 17, 2020. Retrieved15 October 2020.Public Domain This article incorporates text from this source, which is in thepublic domain.
  11. ^McIlwraith CW, Frisbie DD, Kawcak CE (2001). "Nonsteroidal Anti-Inflammatory Drugs".Proc. AAEP.47:182–187.
  12. ^abCotter 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. ^abLees 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.
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
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