MEFENAMIC ACID

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase-2 196 Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9626023	Inhibitor 8297		2.9 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf	Palliative		Approved 8429	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 1981
Primary dysmenorrhea 16 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf	Palliative		Approved 8429	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 1981

C_max

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

T_1/2

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

F_unbound

Value	Dose	Co-administered	Analyte	Population
10% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf	Disc. AE: Gastrointestinal disorder NOS, Skin rash... AEs leading to discontinuation/dose reduction: Gastrointestinal disorder NOS (severe) Skin rash Reaction skin (serious) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf

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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf
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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1037

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
UGT2B7 146 UGT1A9 116 UGT1A3 84 UGT1A1 204 OAT4 146 OAT3 642 OAT1 599 OAT2 145

Drug as perpetrator

Target	Modality	Activity
UGT1A3 93	inhibitor 3277 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250310001602757	no
UGT2B7 157	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17200831/ Page: 4.0	yes [IC50 0.3 uM]
OAT3 644	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3490050/	yes [IC50 0.78 uM]
OAT1 603	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3490050/	yes [IC50 0.83 uM]
OAT2 147	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3490050/	yes [IC50 21.7 uM]
OAT4 146	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3490050/	yes [IC50 61.7 uM]
UGT1A1 254	inhibitor 3277 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250310001602757	yes [Inhibition 25 uM]
UGT1A9 121	inhibitor 3277 Sources: https://www.tandfonline.com/doi/abs/10.1080/00498250310001602757	yes [Inhibition 25 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 1037	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/015034s044lbl.pdf Page: 2.0	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:6717	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6717
ChemicalBook	CB5472051	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5472051
MolPort	MolPort-001-839-968	https://www.molport.com/shop/molecule-link/MolPort-001-839-968
Selleck Chemicals	mefenamic-acid	http://www.selleckchem.com/products/mefenamic-acid.html
ZINC	ZINC000000020241	http://zinc15.docking.org/substances/ZINC000000020241
eMolecules	591932	https://www.emolecules.com/cgi-bin/more?vid=591932

PubMed

Title	Date	PubMed
[A possible adverse effect from the association of losartan-mefenamic acid in hemodialysis].	2001	11385903
The first world report of botulinum A toxin injection for status migrainosus.	2001 Aug	11758858
Increased urinary uronic acid excretion in experimentally-induced renal papillary necrosis in rats.	2001 Jan	11256527
Association of Dental Anaesthetists. Summer Scientific Meeting Stirling, Scotland 8-9 June, 2001. ADA meeting report.	2001 Jul	11862652
Effects of SK&F 96365 and mefenamic acid on Ca2+ influx in stimulated endothelial cells and on endothelium-derived hyperpolarizing factor-mediated arterial hyperpolarization and relaxation.	2001 Jul	11444496
Rapid reactive oxygen species production by mitochondria in endothelial cells exposed to tumor necrosis factor-alpha is mediated by ceramide.	2001 Jun	11415943
Human adult and foetal liver sulphotransferases: inhibition by mefenamic acid and salicylic acid.	2001 Mar	11465392
Synthesis of novel 2,4 (1H, 3H)-quinazolinedione derivatives with analgesic and anti-inflammatory activities.	2001 Mar-Apr	11417393
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	11386636
Competition of tamoxifen with thyroxine for TBG binding: ligand binding assay and computational data.	2001 Nov	11849618
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Selective inhibition of Cl(-) conductance in toad skin by blockers of Cl(-) channels and transporters.	2001 Oct	11546659
Growth and hematological studies on Brazilian children of low socioeconomic level.	2001 Sep	11791475
[A case of nonsteroidal anti-inflammatory drugs (NSAIDs) induced colitis].	2001 Sep	11579497
Prevalence and clinical characteristics of headache in medical students in oman.	2001 Sep	11576205
Nonsteroidal anti-inflammatory drugs for heavy menstrual bleeding.	2002	11869575
Protective role of vitamin E on mefenamic acid-induced alterations in erythrocytes.	2002 Aug	12223096
Describing solubility of polymorphs in mixed solvents by CNIBS/R-K equation.	2002 Dec	12561255
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	12456984
Antipyretics in children.	2002 Jan	11876124
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	11858641
Simultaneous spectrophotometric determination of mefenamic acid and paracetamol in a pharmaceutical preparation using ratio spectra derivative spectrophotometry and chemometric methods.	2002 Jun 15	12049974
The trouble with teething--misdiagnosis and misuse of a topical medicament.	2002 May	12028314
Optimized conditions for MDCK permeability and turbidimetric solubility studies using compounds representative of BCS classes I-IV.	2002 May	11988394
Study of an anaphylactoid reaction to acetaminophen.	2002 May-Jun	12148965
Interactions of human organic anion transporters and human organic cation transporters with nonsteroidal anti-inflammatory drugs.	2002 Nov	12388633
[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	14509173
Surgical versus medical treatment with cyclooxygenase inhibitors for symptomatic patent ductus arteriosus in preterm infants.	2003	12917997
Ibuprofen for the prevention of patent ductus arteriosus in preterm and/or low birth weight infants.	2003	12804505
Demographics, assessment and management of pain in the elderly.	2003	12513114
Effects of anti-inflammatory drugs on convulsant activity of quinolones: a comparative study of drug interaction between quinolones and anti-inflammatory drugs.	2003 Dec	14691652
Comparison of fennel and mefenamic acid for the treatment of primary dysmenorrhea.	2003 Feb	12566188
Menorrhagia: an update.	2003 May	12752071
Effectiveness and mechanism of action of desmopressin in the treatment of copper intrauterine device-related menorrhagia: a pilot study.	2003 Nov	14585881
Determination of selected human pharmaceutical compounds in effluent and surface water samples by high-performance liquid chromatography-electrospray tandem mass spectrometry.	2003 Oct 10	14570326
Determination of nonsteroidal anti-inflammatory drugs, caffeine, and triclosan in wastewater by gas chromatography-mass spectrometry.	2004	15332662
Benefits and risks of pharmacological agents used for the treatment of menorrhagia.	2004	14717620
Solid-state characterization of mefenamic acid.	2004 Apr	14999737
[Acute renal failure--"a well meant present from a friend"].	2004 Dec	15651168
The "high solubility" definition of the current FDA Guidance on Biopharmaceutical Classification System may be too strict for acidic drugs.	2004 Feb	15032311
Liquid chromatography method for determination of mefenamic acid in human serum.	2004 Feb 5	14698254
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	15225193
The use of recombinant human epidermal growth factor (rhEGF) in a gentleman with drug-induced Steven Johnson syndrome.	2004 Jul 15	15347507
The emulsification and solubilisation properties of polyglycolysed oils in self-emulsifying formulations.	2004 Mar	15025855
Salicylidene salicylhydrazide, a selective inhibitor of beta 1-containing GABAA receptors.	2004 May	15100159
Evaluation of the bioactivity of triterpene mixture isolated from Carmona retusa (Vahl.) Masam leaves.	2004 May	15099847
Compounds exhibiting selective efficacy for different beta subunits of human recombinant gamma-aminobutyric acid A receptors.	2004 Nov	15210837
Investigating the environmental transport of human pharmaceuticals to streams in the United Kingdom.	2004 Oct 15	15364527
The occurrence of selected human pharmaceutical compounds in UK estuaries.	2004 Sep	15325211
Tracking acidic pharmaceuticals, caffeine, and triclosan through the wastewater treatment process.	2005 Jan	15683164

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 `Fri Dec 15 14:58:05 GMT 2023` Edited by `admin` on `Fri Dec 15 14:58:05 GMT 2023`
Record UNII	367589PJ2C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MEFENAMIC ACID

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