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)
Molecular Formula | C15H15NO2 |
Molecular Weight | 241.2851 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|
Case report: acute renal failure, thrombocytopenia and nonhemolytic icterus probably caused by mefenamic acid (Parkemed)-dependent antibodies. | 1992 |
|
[Pain management after third molar extraction. Observations of the use of mefenamic acid and rofecoxib in the treatment of postoperative pain in the dental office]. | 2003 |
|
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 |
|
Neotropical Monogenoidea. 43. Diplectanum monticellii n. sp. (Diplectanidae) from the gills of Cynoscion leiarchus (Perciformes: Sciaenidae) in Brazil. | 2003 Aug |
|
Mefenamate, an agent that fails to attenuate experimental cerebral infarction. | 2003 Aug |
|
The use of complexation with alkanolamines to facilitate skin permeation of mefenamic acid. | 2003 Aug 27 |
|
Effects of anti-inflammatory drugs on convulsant activity of quinolones: a comparative study of drug interaction between quinolones and anti-inflammatory drugs. | 2003 Dec |
|
Multiple effects of mefenamic acid on K(+) currents in smooth muscle cells from pig proximal urethra. | 2003 Dec |
|
[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 |
|
Comprehensive study of the luminescent properties and lifetimes of Eu(3+) and Tb(3+) chelated with various ligands in aqueous solutions: influence of the synergic agent, the surfactant and the energy level of the ligand triplet. | 2003 Jun |
|
Menorrhagia: an update. | 2003 May |
|
Investigations on mefenamic acid sustained release tablets with water-insoluble gel. | 2003 May |
|
Salicylate induces tinnitus through activation of cochlear NMDA receptors. | 2003 May 1 |
|
Effectiveness and mechanism of action of desmopressin in the treatment of copper intrauterine device-related menorrhagia: a pilot study. | 2003 Nov |
|
Characterization of bropirimine O-glucuronidation in human liver microsomes. | 2003 Oct |
|
Determination of selected human pharmaceutical compounds in effluent and surface water samples by high-performance liquid chromatography-electrospray tandem mass spectrometry. | 2003 Oct 10 |
|
Interaction between nitric oxide and prostanoids in arterioles of rat cremaster muscle in vivo. | 2003 Sep |
|
[Effect of acetylsalicylic and mefenamic acids on cytoarchitectonic of skin in rats with acute local cryogenic trauma]. | 2003 Sep-Oct |
|
Peritoneal dialysis solutions contract arteries through endothelium-independent prostanoid pathways. | 2004 |
|
Determination of nonsteroidal anti-inflammatory drugs, caffeine, and triclosan in wastewater by gas chromatography-mass spectrometry. | 2004 |
|
Benefits and risks of pharmacological agents used for the treatment of menorrhagia. | 2004 |
|
Solid-state characterization of mefenamic acid. | 2004 Apr |
|
Biological activity of five antibacterial flavonoids from Combretum erythrophyllum (Combretaceae). | 2004 Aug |
|
[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 |
|
Epigallocatechin-3-gallate increases intracellular [Ca2+] in U87 cells mainly by influx of extracellular Ca2+ and partly by release of intracellular stores. | 2004 Feb |
|
Liquid chromatography method for determination of mefenamic acid in human serum. | 2004 Feb 5 |
|
Physicochemical and crystallographic characterization of mefenamic acid complexes with alkanolamines. | 2004 Jan |
|
Double-blind study to evaluate efficacy and safety of meloxicam 7.5 mg and 15 mg versus mefenamic acid 1500 mg in the treatment of primary dysmenorrhea. | 2004 Jul |
|
The use of recombinant human epidermal growth factor (rhEGF) in a gentleman with drug-induced Steven Johnson syndrome. | 2004 Jul 15 |
|
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. | 2004 Jul 2 |
|
Rapid ESI-MS method for examining the thermal decomposition of pharmaceuticals. | 2004 Jun |
|
Rizatriptan versus rizatriptan plus rofecoxib versus rizatriptan plus tolfenamic acid in the acute treatment of migraine. | 2004 Jun 28 |
|
The emulsification and solubilisation properties of polyglycolysed oils in self-emulsifying formulations. | 2004 Mar |
|
Salicylidene salicylhydrazide, a selective inhibitor of beta 1-containing GABAA receptors. | 2004 May |
|
Evaluation of the bioactivity of triterpene mixture isolated from Carmona retusa (Vahl.) Masam leaves. | 2004 May |
|
Factors associated with iron deficiency anemia in Brazilian preschool children. | 2004 May-Jun |
|
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 |
|
Effect of mefenamic acid on controlling irregular uterine bleeding in DMPA users. | 2004 Oct |
|
Mefenamic acid-induced apoptosis in human liver cancer cell-lines through caspase-3 pathway. | 2004 Oct 1 |
|
Investigating the environmental transport of human pharmaceuticals to streams in the United Kingdom. | 2004 Oct 15 |
|
Inhibition of human liver and duodenum sulfotransferases by drugs and dietary chemicals: a review of the literature. | 2004 Sep |
|
The occurrence of selected human pharmaceutical compounds in UK estuaries. | 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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 15:47:01 UTC 2022
by
admin
on
Fri Dec 16 15:47:01 UTC 2022
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Record UNII |
367589PJ2C
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Record Status |
Validated (UNII)
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Record Version |
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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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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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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR |
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METABOLIC ENZYME -> INHIBITOR |
inhibits pradigastat glucuronidation
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
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METABOLITE -> PARENT |
MAJOR
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METABOLITE -> PARENT |
MAJOR
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
Correction factors: for the calculation of contents, multiply the peak areas by 4.0
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
Correction factors: for the calculation of contents, multiply the peak areas by 5.9
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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