Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H15NO2 |
Molecular Weight | 241.2851 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC=CC(NC2=CC=CC=C2C(O)=O)=C1C
InChI
InChIKey=HYYBABOKPJLUIN-UHFFFAOYSA-N
InChI=1S/C15H15NO2/c1-10-6-5-9-13(11(10)2)16-14-8-4-3-7-12(14)15(17)18/h3-9,16H,1-2H3,(H,17,18)
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23656341
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/23656341
Mefenamic acid is a non-steroidal anti-inflammatory agent with analgesic, anti-inflammatory, and antipyretic properties. It is used for the treatment of mild to moderate pain, including menstrual pain, inflammation, and fever. Clinical use of mefenamic acid has generally declined in an era where other NSAID use has flourished. While having modes of action and general toxicities similar to other NSAIDs, mefenamic acid, as a member of the fenamates, nevertheless possesses some unique in vitro effects that have the potential to distinguish this agent from others. Use of this drug remains relevant for pain syndromes and some gynecological disorders, albeit with considerable competition from other NSAIDs. New basic science has considerably improved the understanding of the biochemistry of mefenamic acid. As well as maintaining its use in traditional settings, there is a tremendous potential for expanding the application of mefenamic acid to niche roles. Mefenamic acid binds the prostaglandin synthetase receptors COX-1 and COX-2, inhibiting the action of prostaglandin synthetase. Mefenamic acid concentrations reached during therapy have produced in vivo effects. Prostaglandins sensitize afferent nerves and potentiate the action of bradykinin in inducing pain in animal models. Prostaglandins are mediators of inflammation. Because mefenamic acid is an inhibitor of prostaglandin synthesis, its mode of action may be due to a decrease of prostaglandins in peripheral tissues.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9626023 |
2.9 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | PONSTEL Approved UseMefenamic acid is indicated: For relief of mild to moderate pain in patients ≥ 14 years of age, when therapy will not exceed one week (7 days). For treatment of primary dysmenorrhea. Launch Date3.78691191E11 |
|||
Palliative | PONSTEL Approved UseMefenamic acid is indicated: For relief of mild to moderate pain in patients ≥ 14 years of age, when therapy will not exceed one week (7 days). For treatment of primary dysmenorrhea. Launch Date3.78691191E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5.91 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22116543/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEFENAMIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
3.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7942001/ |
2 mg/kg 1 times / day steady-state, oral dose: 2 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered: |
MEFENAMIC ACID plasma | Homo sapiens population: UNHEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
38.03 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22116543/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEFENAMIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.46 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22116543/ |
250 mg single, oral dose: 250 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEFENAMIC ACID plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
18.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7942001/ |
2 mg/kg 1 times / day steady-state, oral dose: 2 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered: |
MEFENAMIC ACID plasma | Homo sapiens population: UNHEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10% |
500 mg 1 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
MEFENAMIC ACID plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
500 mg 1 times / day steady, oral (starting) Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Gastrointestinal disorder NOS, Skin rash... AEs leading to discontinuation/dose reduction: Gastrointestinal disorder NOS (severe) Sources: Skin rash Reaction skin (serious) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Skin rash | Disc. AE | 500 mg 1 times / day steady, oral (starting) Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Reaction skin | serious Disc. AE |
500 mg 1 times / day steady, oral (starting) Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Gastrointestinal disorder NOS | severe Disc. AE |
500 mg 1 times / day steady, oral (starting) Dose: 500 mg, 1 times / day Route: oral Route: steady Dose: 500 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/17200831/ Page: 4.0 |
yes [IC50 0.3 uM] | |||
yes [IC50 0.78 uM] | ||||
yes [IC50 0.83 uM] | ||||
yes [IC50 21.7 uM] | ||||
yes [IC50 61.7 uM] | ||||
yes [Inhibition 25 uM] | ||||
yes [Inhibition 25 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 2.0 |
yes |
PubMed
Title | Date | PubMed |
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Letter: Aspirin sensitivity: other drugs. | 1975 Feb |
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A case of cardiac arrest following oral 250 mg. mefenamic acid. | 1976 Mar |
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Case report: acute renal failure, thrombocytopenia and nonhemolytic icterus probably caused by mefenamic acid (Parkemed)-dependent antibodies. | 1992 |
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Inhibition of prostaglandin E2 synthesis in abdominal aortic aneurysms: implications for smooth muscle cell viability, inflammatory processes, and the expansion of abdominal aortic aneurysms. | 1999 Jul 6 |
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[A possible adverse effect from the association of losartan-mefenamic acid in hemodialysis]. | 2001 |
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The first world report of botulinum A toxin injection for status migrainosus. | 2001 Aug |
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MiRP2 forms potassium channels in skeletal muscle with Kv3.4 and is associated with periodic paralysis. | 2001 Jan 26 |
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Rapid reactive oxygen species production by mitochondria in endothelial cells exposed to tumor necrosis factor-alpha is mediated by ceramide. | 2001 Jun |
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Acute renal failure from hemoglobinuric and interstitial nephritis secondary to iodine and mefenamic acid. | 2001 Mar |
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Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms. | 2001 Mar |
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Synthesis of novel 2,4 (1H, 3H)-quinazolinedione derivatives with analgesic and anti-inflammatory activities. | 2001 Mar-Apr |
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Competition of tamoxifen with thyroxine for TBG binding: ligand binding assay and computational data. | 2001 Nov |
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Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
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Selective inhibition of Cl(-) conductance in toad skin by blockers of Cl(-) channels and transporters. | 2001 Oct |
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Growth and hematological studies on Brazilian children of low socioeconomic level. | 2001 Sep |
|
Prevalence and clinical characteristics of headache in medical students in oman. | 2001 Sep |
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Protective role of vitamin E on mefenamic acid-induced alterations in erythrocytes. | 2002 Aug |
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Bioactivity studies on beta-sitosterol and its glucoside. | 2002 Aug |
|
Crystal structure of the inclusion complex of beta-cyclodextrin with mefenamic acid from high-resolution synchrotron powder-diffraction data in combination with molecular-mechanics calculations. | 2002 Dec |
|
Aquatic environmental assessment of the top 25 English prescription pharmaceuticals. | 2002 Dec |
|
Simultaneous spectrophotometric determination of mefenamic acid and paracetamol in a pharmaceutical preparation using ratio spectra derivative spectrophotometry and chemometric methods. | 2002 Jun 15 |
|
Development and use of a computer program to detect potentially inappropriate prescribing in older adults residing in Canadian long-term care facilities. | 2002 Oct 14 |
|
Surgical versus medical treatment with cyclooxygenase inhibitors for symptomatic patent ductus arteriosus in preterm infants. | 2003 |
|
Tranexamic acid: a review of its use in the management of menorrhagia. | 2003 |
|
Ibuprofen for the prevention of patent ductus arteriosus in preterm and/or low birth weight infants. | 2003 |
|
Ibuprofen for the treatment of a patent ductus arteriosus in preterm and/or low birth weight infants. | 2003 |
|
Demographics, assessment and management of pain in the elderly. | 2003 |
|
Neotropical Monogenoidea. 43. Diplectanum monticellii n. sp. (Diplectanidae) from the gills of Cynoscion leiarchus (Perciformes: Sciaenidae) in Brazil. | 2003 Aug |
|
Simultaneous determination of arylpropionic acidic non-steroidal anti-inflammatory drugs in pharmaceutical formulations and human plasma by HPLC with UV detection. | 2003 Jan 1 |
|
Green tea catechins evoke a phasic contraction in rat aorta via H2O2-mediated multiple-signalling pathways. | 2003 Jan-Feb |
|
[Variance of bioavailability of pharmaceutical preparations and analysis of factors affecting it]. | 2003 Jul |
|
Vasopressin mediates neuroprotection in mice by stimulation of V1 vasopressin receptors: influence of PI-3 kinase and gap junction inhibitors. | 2003 Jun |
|
Menorrhagia: an update. | 2003 May |
|
Salicylate induces tinnitus through activation of cochlear NMDA receptors. | 2003 May 1 |
|
Characterization of bropirimine O-glucuronidation in human liver microsomes. | 2003 Oct |
|
[Effect of acetylsalicylic and mefenamic acids on cytoarchitectonic of skin in rats with acute local cryogenic trauma]. | 2003 Sep-Oct |
|
Benefits and risks of pharmacological agents used for the treatment of menorrhagia. | 2004 |
|
Solid-state characterization of mefenamic acid. | 2004 Apr |
|
[Acute renal failure--"a well meant present from a friend"]. | 2004 Dec |
|
The "high solubility" definition of the current FDA Guidance on Biopharmaceutical Classification System may be too strict for acidic drugs. | 2004 Feb |
|
Physicochemical and crystallographic characterization of mefenamic acid complexes with alkanolamines. | 2004 Jan |
|
The use of recombinant human epidermal growth factor (rhEGF) in a gentleman with drug-induced Steven Johnson syndrome. | 2004 Jul 15 |
|
The emulsification and solubilisation properties of polyglycolysed oils in self-emulsifying formulations. | 2004 Mar |
|
Evaluation of the bioactivity of triterpene mixture isolated from Carmona retusa (Vahl.) Masam leaves. | 2004 May |
|
Liver injury induced by the non-steroidal anti-inflammatory drug mefenamic acid. | 2004 Nov |
|
Compounds exhibiting selective efficacy for different beta subunits of human recombinant gamma-aminobutyric acid A receptors. | 2004 Nov |
|
Inhibition of human liver and duodenum sulfotransferases by drugs and dietary chemicals: a review of the literature. | 2004 Sep |
|
Dendrimers of citric acid and poly (ethylene glycol) as the new drug-delivery agents. | 2005 Apr |
|
Tracking acidic pharmaceuticals, caffeine, and triclosan through the wastewater treatment process. | 2005 Jan |
Sample Use Guides
For the relief of acute pain in adults and adolescents ≥14 years of age, the recommended dose is 500 mg as an initial dose followed by 250 mg every 6 hours as needed, usually not to exceed one
week.
For the treatment of primary dysmenorrhea, the recommended dose is 500 mg as an initial dose followed by 250 mg every 6 hours, given orally, starting with the onset of bleeding and associated symptoms. Clinical studies indicate that effective treatment can be initiated with the start of menses and should not be necessary for more than 2 to 3 days.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27602398
Mefenamic acid (0-100 uM) exerted cytotoxic effects on oral squamous cell carcinoma (KB), osteogenic sarcoma (Saos-2), and human brain astrocytoma (1321N) cells, where the viability was approximately 75%. Malignant gliomas (U-87MG) cells were resistant to mefenamic acid.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000000160
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NDF-RT |
N0000175722
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WHO-ATC |
M01AG01
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NCI_THESAURUS |
C257
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NDF-RT |
N0000175721
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WHO-VATC |
QM01AG01
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LIVERTOX |
NBK548029
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D008528
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61-68-7
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CHEMBL686
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367589PJ2C
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200-513-1
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MEFENAMIC ACID
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257844
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DB00784
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SUB08703MIG
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1494
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100000091703
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1379605
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6693
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C47599
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2593
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6717
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M7139
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DTXSID5023243
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3115
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4044
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Mefenamic Acid
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1663
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367589PJ2C
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94437
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ACTIVE MOIETY
METABOLITE (PARENT)
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