Meclofenamic acid

{{Drugbox

| image = meclofenamic acid.png

| image_class = skin-invert-image

| tradename = Meclomen

| Drugs.com = {{drugs.com|international|meclofenamic-acid}}

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration = By mouth

| ATC_prefix = M01

| ATC_suffix = AG04

| ATC_supplemental = {{ATC|M02|AA18}}

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| IUPHAR_ligand = 7219

| CAS_number = 644-62-2

| PubChem = 4037

| DrugBank = DB00939

| ChemSpiderID = 3897

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 48I5LU4ZWD

| KEGG = D02341

| ChEBI = 6710

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 509

| IUPAC_name = 2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid

| C=14 | H=11 | Cl=2 | N=1 | O=2

}}

Meclofenamic acid (used as meclofenamate sodium, brand name Meclomen) is a drug used for joint, muscular pain, arthritis and dysmenorrhea.{{cite web|url=http://www.medicinenet.com/meclofenamate/article.htm|title=meclofenamate, Meclomen: Drug Facts, Side Effects and Dosing|website=medicinenet.com}}

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.FDA [http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Set_Current_Drug&ApplNo=018006&DrugName=MECLOMEN&ActiveIngred=MECLOFENAMATE%20SODIUM&SponsorApplicant=PARKE%20DAVIS&ProductMktStatus=3&goto=Search.DrugDetails Meclomen page at FDA]{{dead link|date=May 2025|bot=medic}}{{cbignore|bot=medic}} Page accessed July 3, 2015 Like other members of the class, it is a cyclooxygenase (COX) inhibitor, preventing the formation of prostaglandins.{{cite journal | journal = NIH LiverTox Database | url = http://livertox.nih.gov/MefenamicAcid.htm | title = Mefenamic Acid | date = June 23, 2015 | pmid = 31643176 | access-date = July 3, 2015 }}

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.{{cite book | vauthors = Whitehouse M | chapter = Drugs to Treat Inflammation: A Historical Overview. | pages = 707–729 | title = Frontiers in Medicinal Chemistry | volume = 4 | veditors = Rahman A, etal | publisher = Bentham Science Publishers | date = 2009 | isbn = 978-1-60805-207-3 }}{{rp|718}}

Patents on the drug expired in 1985United States. Congress. Office of Technology Assessment [https://books.google.com/books?id=TrRwM9EpRaAC&pg=PA295 Pharmaceutical R & D: Costs, Risks & Rewards] DIANE Publishing, 1993 {{ISBN|978-0-7881-0468-8}}{{rp|295}} and several generics were introduced in the US, but as of July 2015 only Mylan still sold it.{{cite web | publisher = U.S. Food and Drug Administration | url = http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=MECLOFENAMATE%20SODIUM | title = Meclofenamate sodium ANDAs | archive-url = https://web.archive.org/web/20150604073745/http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=MECLOFENAMATE%20SODIUM | archive-date = 4 June 2015 | access-date = 3 July 2015 }}{{cite web | url = http://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=96f19af4-de8f-4fd7-90d8-55fe6ebdd81d&type=display | title = Mylan label for meclofenamate sodium | date = October 2013 | access-date = 3 July 2015 | work = Daily Med | publisher = U.S. Food and Drug Administration }}

It is not widely used in humans as it has a high rate (30-60%) rate of gastrointestinal side effects.{{cite book | vauthors = Aronson JK | title = Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs | publisher = Elsevier | date = 2009 | isbn = 978-0-08-093294-1 }}{{rp|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. They recommend avoiding NSAIDs in pregnant women at 20 weeks or later in pregnancy.{{cite press release | title=FDA Warns that Using a Type of Pain and Fever Medication in Second Half of Pregnancy Could Lead to Complications | website=U.S. Food and Drug Administration (FDA) | date=15 October 2020 | url=https://www.fda.gov/news-events/press-announcements/fda-warns-using-type-pain-and-fever-medication-second-half-pregnancy-could-lead-complications | archive-url=https://web.archive.org/web/20201016180003/https://www.fda.gov/news-events/press-announcements/fda-warns-using-type-pain-and-fever-medication-second-half-pregnancy-could-lead-complications | url-status=dead | archive-date=October 16, 2020 | access-date=15 October 2020}} {{PD-notice}}{{cite web | title=NSAIDs may cause rare kidney problems in unborn babies | website=U.S. Food and Drug Administration | date=21 July 2017 | url=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 | archive-url=https://web.archive.org/web/20201017014419/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 | url-status=dead | archive-date=October 17, 2020 | access-date=15 October 2020}} {{PD-notice}}

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.{{cite journal | vauthors = McIlwraith CW, Frisbie DD, Kawcak CE | title = Nonsteroidal Anti-Inflammatory Drugs. | journal = Proc. AAEP | date = 2001 | volume = 47 | pages = 182–187 }} It has a relatively slow onset of action, taking 36–48 hours for full effect,{{cite journal | vauthors = Cotter GH, Riley WF, Beck CC, Coppock RW | title = Arquel (Cl- 1583). A new nonsteroidal anti-inflammatory drug for horses | journal = Proceedings. Am Assoc Equine Practnr | date = 1973 | volume = 19 | pages = 81–90 }} and is most useful for treatment of chronic musculoskeletal disease.{{cite journal | vauthors = Snow DH, Baxter P, Whiting B | title = The pharmacokinetics of meclofenamic acid in the horse | journal = Journal of Veterinary Pharmacology and Therapeutics | volume = 4 | issue = 2 | pages = 147–56 | date = June 1981 | pmid = 7349327 | doi = 10.1111/j.1365-2885.1981.tb00724.x }} It has been found to be beneficial for the treatment of navicular syndrome, laminitis, and osteoarthritis, in some cases having a more profound effect than the commonly used NSAID phenylbutazone.{{cite journal | vauthors = Lees P, Higgins AJ | title = Clinical pharmacology and therapeutic uses of non-steroidal anti-inflammatory drugs in the horse | journal = Equine Veterinary Journal | volume = 17 | issue = 2 | pages = 83–96 | date = March 1985 | pmid = 3987667 | doi = 10.1111/j.2042-3306.1985.tb02056.x }} 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.

References

Category:Anthranilic acids

Category:Chlorobenzene derivatives

Category:Equine medications

Category:GABAA receptor positive allosteric modulators