Mefenamic acid - Wikipedia, the free encyclopedia

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Mefenamic acid
From Wikipedia, the free encyclopedia

Mefenamic acid is a non-steroidal anti-inammatory drug used to treat pain, including menstrual pain. It is typically prescribed for oral administration. Mefenamic acid is marketed in the USA as Ponstel and is commonly known in UK as Ponstan. Mefenamic acid decreases inammation (swelling) and uterine contractions by a still unknown mechanism. However it is thought to be related to the inhibition of prostaglandin synthesis. There is also evidence that supports the use of mefenamic acid for perimenstrual migraine headache prophylaxis, with treatment starting 2 days prior to the onset of ow or 1 day prior to the expected onset of the headache and continuing for the duration of [1] menstruation. Since hepatic metabolism plays a signicant role in mefenamic acid elimination, patients with known liver deciency may be prescribed lower doses. Kidney deciency may also cause accumulation of the drug and its metabolites in the excretory system. Therefore patients suering from renal conditions should not be prescribed mefenamic acid.

Mefenamic acid

Systematic (IUPAC) name

2-(2,3-dimethylphenyl)aminobenzoic acid

Clinical data Trade names MedlinePlus Pregnancy cat. Legal status Ponstel, Ponstan a681028 C
(Australia, United States)

AHFS/Drugs.com monograph

Pharmacy Only (S2)

(AU)

Contents
1 Availability 2 Mechanism of action 3 Pharmacokinetics 4 Adverse Reactions 5 Side eects 6 Overdose 7 Synthesis 8 Precautions 9 Brand names 10 References 11 Sources
Routes Bioavailability Protein binding Metabolism Half-life Excretion CAS number ATC code PubChem

-only

(U.S.),

POM

in UK Oral Pharmacokinetic data 90% 90% Hepatic (CYP2C9) 2 hours Renal and fecal Identiers 61-68-7 M01AG01 CID 4044

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Availability
Tablets 100 mg, 250 mg, 500 mg. Capsules: [2] 250 mg. Suspension: 50 mg/5 ml

IUPHAR ligand DrugBank ChemSpider UNII KEGG ChEMBL Formula Mol. mass
SMILES InChI

2593 DB00784 3904 367589PJ2C D00151 CHEMBL686

Mechanism of action
Mefenamic acid is a competitive inhibitor of COX-1 and COX-2, which are responsible for the rst committed step in prostaglandin [3] biosynthesis. Decreasing the activity of these enzymes thus reduces the production of prostaglandins, which are implicated in [4] inammation and pain processes.

Chemical data C15H15NO2 241.285 g/mol

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Pharmacokinetics
Absorption: Rapidly absorbed. Tmax is 2 to 4 h. Cmax is 20 g/mL (single doses). Steady state is reached in 2 days. Distribution: Apparent Vd is 1.06 L/kg. Protein binding is more than 90%. Excreted in breast milk. Metabolism: Metabolized by CYP-450 enzyme CYP2C9 to 3-hydroxymethyl mefenamic acid (metabolite I). Further oxidation to a 3-carboxymefenamic acid (metabolite II) may occur. The metabolites may undergo glucuronidation, and mefenamic acid is also glucuronidated directly. Elimination: Approximately 52% of a dose is excreted into the urine primarily as glucuronides of mefenamic acid (6%), 3-hydroxymefenamic acid (25%), and 3-carboxymefenamic acid (21%). The fecal route of elimination accounts for up to 20% of the dose, mainly in the form of unconjugated 3-carboxymefenamic acid. The half-life [5] is approximately 2 h.

Adverse Reactions
Cardiovascular: CHF; hypertension; syncope; tachycardia. CNS: Dizziness, headache (up to 10%). Dermatologic: Pruritus, rashes (up to 10%). GI: Abdominal pain, constipation, diarrhea, dyspepsia, atulence, GI ulcers (gastric/duodenal), gross bleeding/perforation, heartburn, nausea, vomiting (up to 10%). Hematologic: Anemia, increased bleeding time (up to 10%). Hepatic: Elevated liver enzymes (up to 10%). [6] Miscellaneous: Abnormal renal function, edema, tinnitus (up to 10%)

Side eects
Known mild side eects of mefenamic acid include headaches, nervousness and

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vomiting. Serious side eects may include diarrhea, hematemesis (vomiting blood), haematuria (blood in urine), blurred vision, skin rash, itching and swelling, sore throat and fever. It is advised to consult a doctor immediately if these symptoms appear while taking this medication. Mefenamic acid is recommended to be taken with food.
[7]

Overdose
Overdose can lead to a range of symptoms including convulsions, nausea, emesis, haematemesis, bradypnea, coma. Onset of symptoms is usually between 30 minutes and 4 hours, but signs of renal failure may appear several days after an overdose. Seek medical attention immediately in the case of overdose. The lethal dose can be as low as 2.5 g.

Synthesis
Analogous to fenamic acid, this compound may be synthesized from 2-chlorobenzoic [8] acid and 2,3-dimethylaniline.

Precautions
Mefenamic Acid cannot be expected to substitute for corticosteroids or to treat corticosteroid insuciency. Abrupt discontinuation of corticosteroids may lead to disease exacerbation. Patients on prolonged corticosteroid therapy should have their therapy tapered slowly if a decision is made to discontinue corticosteroids. The pharmacological activity of Mefenamic Acid in reducing fever and inammation may diminish the utility of these diagnostic signs in detecting complications of presumed noninfectious, painful conditions. Renal and hepatic impairment, asthma. Monitor blood [9] counts and liver function during long-term therapy.

Brand names
Beafemic, Mefalth, Mefalth T, Mevan, Ponstel, Ponstan, Ponstal, Parkemed, Revalan, Mafepain, Mefamed, Mephadolor, Meftal, Dyfenamic, Potalon, Dolfenal, Meyerdonal, Alfoxan, Fenagesic, Fenamin, Spiralgin, Almus, Mefacit, Pangesic Forte

References
1. ^ Pringsheim, T.; Davenport, W. J.; Dodick, D. (2008). "Acute Treatment and Prevention of Menstrually Related Migraine Headache: Evidence-Based Review". Neurology 70 (17): 15551563. PMID 18427072 (//www.ncbi.nlm.nih.gov/pubmed/18427072). 2. ^ National formulary of India, 4th Ed. New Delhi, India, Indian Pharmacopoeia commission; 2011: 7 3. ^ http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2720641/ 4. ^ http://onlinelibrary.wiley.com/doi/10.1038/sj.bjp.0704092

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5. 6. 7. 8.

9.

/abstract;jsessionid=62C075BC55DE8389CE3C56CBD0035181.d03t03 ^ http://www.drugs.com/ppa/mefenamic-acid.html ^ http://www.drugs.com/ppa/mefenamic-acid.html ^ "Side eects for Mefenamic Acid" (http://www.nlm.nih.gov/medlineplus/druginfo /meds/a681028.html#side-eects). Medline Plus. National Institutes of Health. ^ Trinus, F. P .; Mokhort, N. A.; Yagupol'skii, L. M.; Fadeicheva, A. G.; Danilenko, V. S.; Ryabukha, T. K.; Fialkov, Yu. A.; Kirichek, L. M.; Endel'man, . S.; Get'man, G. A. (1977). "Mefenamic acid A Nonsteroid Antiinammatory Agent". Pharmaceutical Chemistry Journal 11 (12): 17061711. doi:10.1007/BF00778304 (http://dx.doi.org /10.1007%2FBF00778304). ^ http://www.drugsupdate.com/generic/view/285

Sources
MedlinePlus Drug Information: Mefenamic Acid (http://www.nlm.nih.gov /medlineplus/druginfo/medmaster/a681028.html). Last accessed September 28, 2005. Ponstel Pharmacology, Pharmacokinetics, Studies, Metabolism - Mefenamic Acid RxList Monographs (http://www.rxlist.com/cgi/generic3/mefenamic_cp.htm). Last accessed September 28, 2005. Consumption of NSAIDs and the Development of Congestive Heart Failure in Elderly Patients (http://archinte.ama-assn.org/cgi/content/abstract/160/6/777) NSAIDs May Increase Risk for Worsening Heart Failure (http://cardiology.jwatch.org/cgi/content/full/2002/315/3) Retrieved from "http://en.wikipedia.org/w/index.php?title=Mefenamic_acid& oldid=574456866" Categories: Non-steroidal anti-inammatory drugs Anthranilic acids This page was last modied on 25 September 2013 at 12:53. Text is available under the Creative Commons Attribution-ShareAlike License; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia is a registered trademark of the Wikimedia Foundation, Inc., a non-prot organization.

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