U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of MEFENAMIC ACID

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)

HIDE SMILES / InChI

Description
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.

Originator

Curator's Comment: Scientists led by Claude Winder from Parke-Davis invented mefenamic acid in 1961

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.9 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PONSTEL

Approved Use

Mefenamic 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 Date

3.78691191E11
Palliative
PONSTEL

Approved Use

Mefenamic 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 Date

3.78691191E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
5.91 μg/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
38.03 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
3.46 h
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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
Disc. AE: Gastrointestinal disorder NOS, Skin rash...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal disorder NOS (severe)
Skin rash
Reaction skin (serious)
Sources:
AEs

AEs

AESignificanceDosePopulation
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
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
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer








Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Letter: Aspirin sensitivity: other drugs.
1975 Feb
A case of cardiac arrest following oral 250 mg. mefenamic acid.
1976 Mar
Case report: acute renal failure, thrombocytopenia and nonhemolytic icterus probably caused by mefenamic acid (Parkemed)-dependent antibodies.
1992
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
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
Rapid reactive oxygen species production by mitochondria in endothelial cells exposed to tumor necrosis factor-alpha is mediated by ceramide.
2001 Jun
Acute renal failure from hemoglobinuric and interstitial nephritis secondary to iodine and mefenamic acid.
2001 Mar
Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms.
2001 Mar
Synthesis of novel 2,4 (1H, 3H)-quinazolinedione derivatives with analgesic and anti-inflammatory activities.
2001 Mar-Apr
Competition of tamoxifen with thyroxine for TBG binding: ligand binding assay and computational data.
2001 Nov
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Selective inhibition of Cl(-) conductance in toad skin by blockers of Cl(-) channels and transporters.
2001 Oct
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
Protective role of vitamin E on mefenamic acid-induced alterations in erythrocytes.
2002 Aug
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
Patents

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
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
MEFENAMIC ACID
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
GARDAN
Brand Name English
M01AG01
Code English
PONSTEL
Brand Name English
N-2,3-Xylylanthranilic acid
Systematic Name English
CI-473
Code English
CN-35355
Code English
MEFENAMATE
Common Name English
MEFENAMIC ACID [EP MONOGRAPH]
Common Name English
MEFENAMIC ACID [MART.]
Common Name English
MEFENAMINIC ACID
Common Name English
NSC-94437
Code English
2-(2,3-DIMETHYLPHENYL)AMINOBENZOIC ACID
Systematic Name English
BENZOIC ACID, 2-(2,3-DIMETHYLPHENYL)AMINO-
Common Name English
MEFENAMIC ACID [VANDF]
Common Name English
J2.344B
Code English
MEFENAMIC ACID [MI]
Common Name English
MEPHENAMIC ACID
Common Name English
MEFENAMIC ACID [HSDB]
Common Name English
MEFENAMIC ACID [USP MONOGRAPH]
Common Name English
MEFENAMIC ACID [USAN]
Common Name English
MEFENAMIC ACID [JAN]
Common Name English
MEFENAMIC ACID [USP-RS]
Common Name English
MEFENAMIC ACID [ORANGE BOOK]
Common Name English
mefenamic acid [INN]
Common Name English
Mefenamic acid [WHO-DD]
Common Name English
INF-3355
Code English
MEPHENAMINIC ACID
Common Name English
Classification Tree Code System Code
NDF-RT N0000000160
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
NDF-RT N0000175722
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
WHO-ATC M01AG01
Created by admin on Wed Jul 05 22:30:10 UTC 2023 , Edited by admin on Wed Jul 05 22:30:10 UTC 2023
NCI_THESAURUS C257
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
NDF-RT N0000175721
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
WHO-VATC QM01AG01
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
LIVERTOX NBK548029
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
Code System Code Type Description
MESH
D008528
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
CAS
61-68-7
Created by admin on Wed Jul 05 22:30:10 UTC 2023 , Edited by admin on Wed Jul 05 22:30:10 UTC 2023
PRIMARY
ChEMBL
CHEMBL686
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
DAILYMED
367589PJ2C
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-513-1
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
WIKIPEDIA
MEFENAMIC ACID
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
RXCUI
257844
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
ALTERNATIVE
DRUG BANK
DB00784
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
EVMPD
SUB08703MIG
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
INN
1494
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
SMS_ID
100000091703
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
RS_ITEM_NUM
1379605
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
RXCUI
6693
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY RxNorm
NCI_THESAURUS
C47599
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
IUPHAR
2593
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
CHEBI
6717
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
MERCK INDEX
M7139
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID5023243
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
HSDB
3115
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
PUBCHEM
4044
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
LACTMED
Mefenamic Acid
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
DRUG CENTRAL
1663
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
FDA UNII
367589PJ2C
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY
NSC
94437
Created by admin on Wed Jul 05 22:30:11 UTC 2023 , Edited by admin on Wed Jul 05 22:30:11 UTC 2023
PRIMARY