Mefenamic acid

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Mefenamic acid

Clinical data

Trade names Ponstel, Ponstan, others

AHFS/Drugs.com Monograph

MedlinePlus a681028

Pregnancy  AU: C
category  US: C (Risk not ruled out)

Routes of by mouth
administration
ATC code  M01AG01 (WHO)
Legal status
Legal status  AU: S2 (Pharmacy only)
 UK: POM (Prescription only)
  US: ℞-only

Pharmacokinetic data
Bioavailability 90%
Protein binding 90%
Metabolism Hepatic (CYP2C9)
Elimination half- 2 hours
life
Excretion Urine (66%), faeces (20-25%)
Identifiers
IUPAC name[show]
CAS Number  61-68-7
PubChem CID  4044
IUPHAR/BPS  2593
DrugBank  DB00784
ChemSpider  3904
UNII  367589PJ2C
KEGG  D00151
ChEBI  CHEBI:6717
ChEMBL  CHEMBL686
ECHA InfoCard 100.000.467
Chemical and physical data
Formula C15H15NO2
Molar mass 241.285 g/mol
3D model (JSmol) Interactive image

SMILES[show]

InChI[show]
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Mefenamic acid is a member of the anthranilic acid derivatives (or fenamate) class of NSAID drugs,
and is used to treat mild to moderate pain, including menstrual pain, and is sometimes used to
 prevent migraines associated with menstruation.[1][2] It is not widely used in the United States due to
its side effects and high cost compared to other NSAID drugs.[3][4]:334
Its name derives from its systematic name, dimethylphenylaminobenzoic acid. It was discovered
and brought to market by Parke-Davis in the 1960s. It became generic in the 1980s and is available
worldwide under many brand names.[5] As of 2015 the cost for a typical course of medication in the
United States is more than 200 USD.[6]

Contents

 1Medical use
 2Side effects
 3Mechanism of action
 4History
 5Society and culture
o 5.1Availability and pricing
o 5.2Synthesis
 6Research
 7See also
 8References
 9Sources

Medical use[edit]
Mefenamic acid is used to treat moderate pain and menstrual pain.[1]
There is evidence that supports the use of mefenamic acid for perimenstrual migraine
headache prophylaxis, with treatment starting 2 days prior to the onset of flow or 1 day prior to the
expected onset of the headache and continuing for the duration of menstruation.[2]

Side effects[edit]
Mefenamic acid is recommended to be taken with food.[7]
Known mild side effects of mefenamic acid include headaches, nervousness, and vomiting. Serious
side effects may include diarrhea, hematemesis (vomiting blood), hematuria (blood in urine), blurred
vision, skin rash, itching and swelling, sore throat and fever.[4]:334 It has been associated with acute
liver damage.[3]
In 2008 the US label was updated with a warning concerning a risk of premature closure of
the ductus arteriosus in pregnancy.[8]

Mechanism of action[edit]
Like other members of the anthranilic acid derivatives (or fenamate) class of NSAID drugs, it inhibits
both isoforms of COX and prevents formation of prostaglandins.[3][9]

History[edit]
Scientists led by Claude Winder from Parke-Davis invented mefenamic acid in 1961, along with
fellow members of the class of anthranilic acid derivatives, flufenamic acid in 1963
and meclofenamate sodium in 1964.[10]:718 U.S. Patent 3,138,636 on the drug was issued in
1964.[11][12]:918–919
It was approved in the UK in 1963 as "Ponstan", in West Germany in 1964 as "Ponalar", and in
France as "Ponstyl" and the US in 1967 as "Ponstel".[3][12]:918–919

Society and culture[edit]

Availability and pricing[edit]
Mefenamic acid is generic and is available worldwide under many brand names.[5]
In the USA, wholesale price of a week's supply of generic mefenamic acid has been quoted as
$426.90 in 2014. Brand-name Ponstel is $571.70.[13] In contrast, in the UK, a weeks supply is £1.66,
or £8.17 for branded Ponstan.[14] In the Philippines, 10 tablets of 500 mg generic mefenamic acid
cost PHP39.00 (or the equivalent of $0.88USD) as of October 25, 2014.
Synthesis[edit]
Analogous to fenamic acid, this compound may be made from 2-chlorobenzoic acid and 2,3-
dimethylaniline.[15]

Research[edit]
While studies have been conducted to see if mefenamic acid can improve behavior in transgenic
mouse models of Alzheimer's disease[16][17] there is no good evidence that mefenamic acid or
other NSAIDs can treat or prevent Alzheimer's in humans; clinical trials of NSAIDs other than
mefenamic acid for treatment of Alzheimer's have found more harm than benefit.[18][19][20]

See also[edit]
 Niflumic acid

References[edit]
1. ^ Jump up to:a b FDA Ponstel Label Updated February 19, 2008
2. ^ Jump up to:a b Pringsheim T, Davenport WJ, Dodick D (April 2008). "Acute
treatment and prevention of menstrually related migraine headache: evidence-
based review". Neurology. 70 (17): 1555–
63. doi:10.1212/01.wnl.0000310638.54698.36. PMID 18427072.
3. ^ Jump up to:a b c d NIH LiverTox Database Mefenamic Acid Last updated June
23, 2015. Page accessed July 3, 2015
4. ^ Jump up to:a b Jeffrey K. Aronson. Meyler's Side Effects of Analgesics and Anti-
inflammatory Drugs. Elsevier, 2009 ISBN 9780080932941
5. ^ Jump up to:a b Drugs.com drugs.com international listings for mefenamic
acid Page accessed July 3, 2015
6. Jump up^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015
Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. X. ISBN 9781284057560.
7. Jump up^ "Side effects for Mefenamic Acid". Medline Plus. National Institutes of
Health.
8. Jump up^ FDA March 2008 FDA advisory
9. Jump up^ Prusakiewicz JJ, Duggan KC, Rouzer CA, Marnett LJ (August 2009).
"Differential sensitivity and mechanism of inhibition of COX-2 oxygenation of
arachidonic acid and 2-arachidonoylglycerol by ibuprofen and mefenamic
acid". Biochemistry. 48 (31): 7353–5. doi:10.1021/bi900999z. PMID 19603831.
10. Jump up^ 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
11. Jump up^ US Patent 3,138,636
12. ^ Jump up to:a b Marshall Sittig Pharmaceutical Manufacturing Encyclopedia
Volume 1 A-KArchived 2007-10-23 at the Wayback Machine. Second Edition,
Reprint Edition. Noyes Publications, 1988
13. Jump up^ Drugs for Osteoarthritis. The Medical Letter, 56(1450):80-84,
September 2014
14. Jump up^ https://www.medicinescomplete.com/mc/bnf/current/PHP6487-
mefenamic-acid-non-proprietary.htm accessed 19th sept 2014
15. Jump up^ Trinus FP, Mokhort NA, Yagupol'skii LM, Fadeicheva AG, Danilenko
VS, Ryabukha TK, Fialkov YA, Kirichek LM, Endel'man ÉS, Get'man GA (1977).
"Mefenamic acid — A Nonsteroid Antiinflammatory Agent". Pharmaceutical
Chemistry Journal. 11 (12): 1706–1711. doi:10.1007/BF00778304.
16. Jump up^ Joo Y, Kim HS, Woo RS, Park CH, Shin KY, Lee JP, Chang KA, Kim
S, Suh YH (January 2006). "Mefenamic acid shows neuroprotective effects and
improves cognitive impairment in in vitro and in vivo Alzheimer's disease
models". Molecular Pharmacology. 69 (1): 76–
84. doi:10.1124/mol.105.015206. PMID 16223958.
17. Jump up^ Daniels MJ, Rivers-Auty J, Schilling T, Spencer NG, Watremez W,
Fasolino V, et al. (August 2016). "Fenamate NSAIDs inhibit the NLRP3
inflammasome and protect against Alzheimer's disease in rodent
models". Nature Communications. 7:
12504. doi:10.1038/ncomms12504. PMID 27509875.
18. Jump up^ Miguel-Álvarez M, Santos-Lozano A, Sanchis-Gomar F, Fiuza-Luces
C, Pareja-Galeano H, Garatachea N, Lucia A (February 2015). "Non-steroidal
anti-inflammatory drugs as a treatment for Alzheimer's disease: a systematic
review and meta-analysis of treatment effect". Drugs & Aging. 32 (2): 139–
47. doi:10.1007/s40266-015-0239-z. PMID 25644018.
19. Jump up^ Jaturapatporn D, Isaac MG, McCleery J, Tabet N (February 2012).
"Aspirin, steroidal and non-steroidal anti-inflammatory drugs for the treatment of
Alzheimer's disease". The Cochrane Database of Systematic Reviews (2):
CD006378. doi:10.1002/14651858.CD006378.pub2. PMID 22336816.
20. Jump up^ Wang J, Tan L, Wang HF, Tan CC, Meng XF, Wang C, Tang SW, Yu
JT. "Anti-inflammatory drugs and risk of Alzheimer's disease: an updated
systematic review and meta-analysis". Journal of Alzheimer's Disease. 44 (2):
385–96. doi:10.3233/JAD-141506. PMID 25227314.