Mefenamic acid

Mefenamic acid
Mefenamic acid
Systematic (IUPAC) name
2-(2,3-dimethylphenyl)aminobenzoic acid
Clinical data
Trade names Ponstel
AHFS/Drugs.com monograph
MedlinePlus a681028
Pregnancy cat. C (Australia, United States)
Legal status ℞-only (U.S.), POM in UK
Routes Oral
Pharmacokinetic data
Bioavailability 90%
Protein binding 90%
Metabolism Hepatic (CYP2C9)
Half-life 2 hours
Excretion Renal and fecal
Identifiers
CAS number 61-68-7 YesY
ATC code M01AG01
PubChem CID 4044
DrugBank APRD0073
ChemSpider 3904 YesY
UNII 367589PJ2C YesY
KEGG D00151 YesY
ChEMBL CHEMBL686 YesY
Chemical data
Formula C15H15NO2 
Mol. mass 241.285 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  acid (verify)

Mefenamic acid is a non-steroidal anti-inflammatory drug used to treat pain, including menstrual pain. It is typically prescribed for oral administration. Mefenamic acid is marketed in the USA as Ponstel.

Mefenamic acid decreases inflammation (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 flow or 1 day prior to the expected onset of the headache and continuing for the duration of menstruation.[1]

Since hepatic metabolism plays a significant role in mefenamic acid elimination, patients with known liver deficiency may be prescribed lower doses. Kidney deficiency may also cause accumulation of the drug and its metabolites in the excretory system. Therefore patients suffering from renal conditions should not be prescribed mefenamic acid.

Brand Names
Mefalth, Mefalth T, Ponstel, Ponstan, Ponstal, Parkemed, Mafepain, Mefamed, Mephadolor, Meftal, Dyfenamic, Potarlon, Dolfenal, Meyerdonal, Alfoxan, Fenagesic, Spiralgin.

Contents

Side effects

Known mild side effects of mefenamic acid include headaches, nervousness and vomiting. Serious side effects 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.

Non-steroidal anti-inflammatory drugs (NSAIDs) may worsen hypertension. Persons with hypertension, left ventricular dysfunction, and heart failure may wish to avoid NSAIDs.

Mefenamic acid is recommended to be taken with food.[2]

Mefenamic acid usage has been discontinued in Germany in 2007 because no study to date could prove any advantage over other NSAIDs, but some severe side-effects have been observed. [3]

Overdose

Overdose can lead to a range of symptoms including convulsions, nausea, vomiting, vomiting blood, shallow breathing, 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 2.5g.

Synthesis

Analogous to fenamic acid, this compound may be synthesized from 2-chlorobenzoic acid and 2,3-dimethylaniline.[4]

References

  1. ^ Pringsheim T, Davenport WJ, Dodick D. Acute treatment and prevention of menstrually related migraine headache: evidence-based review. Neurology. 2008;70(17):1555-1563.
  2. ^ National Institutes of Health side effects for Mefenamic Acid
  3. ^ http://www.qualimedic.de/Sprechstunde/arzneimittel_nebenwirkung/7182967
  4. ^ 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. et al. (1977). "Mefenamic acid — A nonsteroid antiinflammatory agent". Pharmaceutical Chemistry Journal 11 (12): 1706. doi:10.1007/BF00778304. 

Sources


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Look at other dictionaries:

  • mefenamic acid — mefenamo rūgštis statusas T sritis chemija formulė (CH₃)₂C₆H₃NHC₆H₄COOH atitikmenys: angl. mefenamic acid rus. мефенамовая кислота ryšiai: sinonimas – 2 (2,3 dimetilfenilamino)benzenkarboksirūgštis …   Chemijos terminų aiškinamasis žodynas

  • mefenamic acid — noun a nonsteroidal anti inflammatory and analgesic drug (trade name Ponstel) used to treat mild pain (especially menstrual cramps) • Syn: ↑Ponstel • Hypernyms: ↑nonsteroidal anti inflammatory, ↑nonsteroidal anti inflammatory drug, ↑NSAID * * *… …   Useful english dictionary

  • mefenamic acid — noun Etymology: dimethyl + fen (by shortening & alteration from phenyl) + aminobenzoic acid Date: 1962 a drug C15H15NO2 used as an anti inflammatory agent …   New Collegiate Dictionary

  • mefenamic acid — /mef euh nam ik, mef /, Pharm. a white powder, C15H15NO2, used as a mild analgesic, anti inflammatory, and antipyretic in certain types of arthritis and for the relief of moderate short term pain due to dysmenorrhea. [1960 65; ME(THYL) + fen ,… …   Universalium

  • mefenamic acid — An aspirinlike analgesic with antiinflammatory properties. * * * mef·e·nam·ic acid .mef ə .nam ik n a drug C15H15NO2 used as an anti inflammatory and analgesic agent * * * an anti inflammatory drug (see NSAID) used to treat headache, toothache,… …   Medical dictionary

  • mefenamic acid — noun A nonsteroidal anti inflammatory drug used to treat pain, including menstrual pain …   Wiktionary

  • mefenamic acid — an anti inflammatory drug (see NSAID) used to treat headache, toothache, rheumatic pain, and similar conditions. It is administered by mouth; side effects include digestive upsets, drowsiness, and skin rashes. Trade names: Ponstan …   The new mediacal dictionary

  • Кислота Мефенаминовая (Mefenamic Acid) — противовоспалительное лекарственное вещество (см. Вещество лекарственное нестероидное противовоспалительное); применяется для лечения головной, зубной, ревматической боли и аналогичных состояний. Назначается внутрь; возможные побочные эффекты:… …   Медицинские термины

  • Fenamic acid — IUPAC name 2 (phenylamino)benzoic acid …   Wikipedia

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