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

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

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
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
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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:30:10 UTC 2023
Edited
by admin
on Wed Jul 05 22:30:10 UTC 2023
Record UNII
367589PJ2C
Record Status Validated (UNII)
Record Version
  • Download
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
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