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Details

Stereochemistry ACHIRAL
Molecular Formula C15H15NO2
Molecular Weight 241.2851
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEFENAMIC ACID

SMILES

CC1=C(C)C(NC2=CC=CC=C2C(O)=O)=CC=C1

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
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.9 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
PONSTEL
Palliative
PONSTEL
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

In Vivo Use Guide
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
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 Tue Oct 22 00:43:26 UTC 2019
Edited
by admin
on Tue Oct 22 00:43:26 UTC 2019
Record UNII
367589PJ2C
Record Status Validated (UNII)
Record Version
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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
MEFENAMIC ACID [USP]
Common Name English
N-2,3-XYLYLANTHRANILIC ACID
Systematic Name English
CI-473
Code English
CN-35355
Code 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 [USAN]
Common Name English
MEFENAMIC ACID [JAN]
Common Name English
MEFENAMIC ACID [USP-RS]
Common Name English
MEFENAMIC ACID [WHO-DD]
Common Name English
MEFENAMIC ACID [EP]
Common Name English
MEFENAMIC ACID [ORANGE BOOK]
Common Name English
MEFENAMIC ACID [INN]
Common Name English
INF-3355
Code English
MEPHENAMINIC ACID
Common Name English
Classification Tree Code System Code
NDF-RT N0000000160
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
NDF-RT N0000175722
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
WHO-ATC M01AG01
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
NCI_THESAURUS C257
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
NDF-RT N0000175721
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
WHO-VATC QM01AG01
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
LIVERTOX 591
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
Code System Code Type Description
MESH
D008528
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
CAS
61-68-7
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
ChEMBL
CHEMBL686
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
ECHA (EC/EINECS)
200-513-1
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
WIKIPEDIA
MEFENAMIC ACID
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
RXCUI
257844
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
DRUG BANK
DB00784
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
EVMPD
SUB08703MIG
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
INN
1494
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
RXCUI
6693
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C47599
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
IUPHAR
2593
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
MERCK INDEX
M7139
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY Merck Index
EPA CompTox
61-68-7
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
HSDB
61-68-7
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
PUBCHEM
4044
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
LactMed
61-68-7
Created by admin on Tue Oct 22 00:43:26 UTC 2019 , Edited by admin on Tue Oct 22 00:43:26 UTC 2019
PRIMARY
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