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 |
---|---|---|
Letter: Aspirin sensitivity: other drugs. | 1975 Feb |
|
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 |
|
[A possible adverse effect from the association of losartan-mefenamic acid in hemodialysis]. | 2001 |
|
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations. | 2001 |
|
Clinical and pathological overlap in nonsteroidal anti-inflammatory drug-related small bowel diaphragm disease and the neuromuscular and vascular hamartoma of the small bowel. | 2001 Apr |
|
The first world report of botulinum A toxin injection for status migrainosus. | 2001 Aug |
|
MiRP2 forms potassium channels in skeletal muscle with Kv3.4 and is associated with periodic paralysis. | 2001 Jan 26 |
|
Association of Dental Anaesthetists. Summer Scientific Meeting Stirling, Scotland 8-9 June, 2001. ADA meeting report. | 2001 Jul |
|
Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms. | 2001 Mar |
|
Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation. | 2001 May-Jun |
|
Growth and hematological studies on Brazilian children of low socioeconomic level. | 2001 Sep |
|
[A case of nonsteroidal anti-inflammatory drugs (NSAIDs) induced colitis]. | 2001 Sep |
|
Nonsteroidal anti-inflammatory drugs for heavy menstrual bleeding. | 2002 |
|
Protective role of vitamin E on mefenamic acid-induced alterations in erythrocytes. | 2002 Aug |
|
Bioactivity studies on beta-sitosterol and its glucoside. | 2002 Aug |
|
Describing solubility of polymorphs in mixed solvents by CNIBS/R-K equation. | 2002 Dec |
|
Molecular modelling of the differential interaction between several non-steroidal anti-inflammatory drugs and human prostaglandin endoperoxide H synthase-2 (h-PGHS-2). | 2002 Jan |
|
Characterization of mefenamic acid-guaiacol ester: stability and transport across Caco-2 cell monolayers. | 2002 Jul |
|
Simultaneous spectrophotometric determination of mefenamic acid and paracetamol in a pharmaceutical preparation using ratio spectra derivative spectrophotometry and chemometric methods. | 2002 Jun 15 |
|
Interactions of human organic anion transporters and human organic cation transporters with nonsteroidal anti-inflammatory drugs. | 2002 Nov |
|
Structure-function relationship and role of tumor necrosis factor-alpha-converting enzyme in the down-regulation of L-selectin by non-steroidal anti-inflammatory drugs. | 2002 Oct 11 |
|
Tranexamic acid: a review of its use in the management of menorrhagia. | 2003 |
|
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 |
|
Comparison of fennel and mefenamic acid for the treatment of primary dysmenorrhea. | 2003 Feb |
|
Essential requirements for substrate binding affinity and selectivity toward human CYP2 family enzymes. | 2003 Jan 1 |
|
Green tea catechins evoke a phasic contraction in rat aorta via H2O2-mediated multiple-signalling pathways. | 2003 Jan-Feb |
|
Vasopressin mediates neuroprotection in mice by stimulation of V1 vasopressin receptors: influence of PI-3 kinase and gap junction inhibitors. | 2003 Jun |
|
Investigations on mefenamic acid sustained release tablets with water-insoluble gel. | 2003 May |
|
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 |
|
Peritoneal dialysis solutions contract arteries through endothelium-independent prostanoid pathways. | 2004 |
|
Biological activity of five antibacterial flavonoids from Combretum erythrophyllum (Combretaceae). | 2004 Aug |
|
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 |
|
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 |
|
Factors associated with iron deficiency anemia in Brazilian preschool children. | 2004 May-Jun |
|
Effect of mefenamic acid on controlling irregular uterine bleeding in DMPA users. | 2004 Oct |
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
Wed Jul 05 22:30:10 UTC 2023
by
admin
on
Wed Jul 05 22:30:10 UTC 2023
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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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PRIMARY | |||
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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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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> INHIBITOR |
inhibits pradigastat glucuronidation
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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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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)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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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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ACTIVE MOIETY |
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