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 |
---|---|---|
Case report: acute renal failure, thrombocytopenia and nonhemolytic icterus probably caused by mefenamic acid (Parkemed)-dependent antibodies. | 1992 |
|
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 |
|
Renal papillary necrosis. | 2002 Nov-Dec |
|
The enhancing effect of a triethanolamine-ethanol-isopropyl myristate mixed system on the skin permeation of acidic drugs. | 2002 Oct |
|
Surgical versus medical treatment with cyclooxygenase inhibitors for symptomatic patent ductus arteriosus in preterm infants. | 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 |
|
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 |
|
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 |
|
[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 |
|
Inactivation of creatine kinase during the interaction of mefenamic acid with horseradish peroxidase and hydrogen peroxide: participation by the mefenamic acid radical. | 2003 Mar 14 |
|
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 |
|
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 |
|
Liquid chromatography method for determination of mefenamic acid in human serum. | 2004 Feb 5 |
|
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NDF-RT |
N0000000160
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
||
|
NDF-RT |
N0000175722
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
||
|
WHO-ATC |
M01AG01
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
||
|
NCI_THESAURUS |
C257
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
||
|
NDF-RT |
N0000175721
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
||
|
WHO-VATC |
QM01AG01
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
||
|
LIVERTOX |
NBK548029
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
D008528
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
61-68-7
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
CHEMBL686
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
367589PJ2C
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
200-513-1
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
MEFENAMIC ACID
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
257844
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
ALTERNATIVE | |||
|
DB00784
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
SUB08703MIG
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
1494
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
1379605
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
6693
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | RxNorm | ||
|
C47599
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
2593
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
6717
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
M7139
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | Merck Index | ||
|
DTXSID5023243
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
3115
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
4044
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
Mefenamic Acid
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
1663
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
367589PJ2C
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY | |||
|
94437
Created by
admin on Fri Dec 16 15:47:01 UTC 2022 , Edited by admin on Fri Dec 16 15:47:01 UTC 2022
|
PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)