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M4267

Sigma-Aldrich

Mefenamic acid

Synonym(s):

2-[(2,3-Dimethylphenyl)amino]benzoic acid, N-(2,3-Xylyl)anthranilic acid

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About This Item

Empirical Formula (Hill Notation):
C15H15NO2
CAS Number:
61-68-7
Molecular Weight:
241.29
EC Number:
200-513-1
MDL number:
MFCD00051721
UNSPSC Code:
12161501
PubChem Substance ID:
24896815
NACRES:
NA.77

originator

Shionogi

SMILES string

Cc1cccc(Nc2ccccc2C(O)=O)c1C

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)

InChI key

HYYBABOKPJLUIN-UHFFFAOYSA-N

Gene Information

human ... PTGS1(5742) , PTGS2(5743)

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Application

Mefenamic acid has been used:
  • to test its hepatotoxic effect in the transgenic zebrafish cell line (LiPan)
  • to test its neuroprotective functionality in zebrafish embryos/larvae
  • in the preparation of mucoadhesive microparticles in hydrogel beads

An NSAID. Circumvents MRP-mediated multidrug resistance. Specifically and significantly potentiates the cytotoxicity of anthracyclines as well as teniposide, VP-16 and vincristine.

Biochem/physiol Actions

Mefenamic acid is an analgesic and anti-inflammatory drug. It acts as a cyclooxygenase (COX) enzyme inhibitor. It is hepatoxic and implicated in liver injury. Contrarily, mefenamic acid elicits neuroprotection in in vivo ischemic stroke models by inhibiting cell toxicity induced by glutamate. Mefenamic due its inhibitory effect on prostaglandin synthesis can be used in reducing edema and ache.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Dopamine and Norepinephrine Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Shionogi. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Filitsa Dimiza et al.
Dalton transactions (Cambridge, England : 2003), 40(34), 8555-8568 (2011-08-02)
Copper(II) complexes with the non-steroidal antiinflammatory drug mefenamic acid in the presence of aqua or nitrogen donor heterocyclic ligands (2,2'-bipyridine, 1,10-phenanthroline, 2,2'-bipyridylamine or pyridine) have been synthesized and characterized. The crystal structures of [(2,2'-bipyridine)bis(mefenamato)copper(II)], 2, [(2,2'-bipyridylamine)bis(mefenamato)copper(II)], 4, and [bis(pyridine)bis(methanol)bis(mefenamato)copper(II)], 5
Taro Kojima et al.
Pharmaceutical research, 29(10), 2777-2791 (2012-01-06)
The stabilization mechanism of a supersaturated solution of mefenamic acid (MFA) from a solid dispersion with EUDRAGIT(®) EPO (EPO) was investigated. The solid dispersions were prepared by cryogenic grinding method. Powder X-ray diffractometry, in vitro dissolution test, in vivo oral
Janesh Gupta et al.
The New England journal of medicine, 368(2), 128-137 (2013-01-11)
Menorrhagia is a common problem, yet evidence to inform decisions about therapy is limited. In a pragmatic, multicenter, randomized trial, we compared the levonorgestrel-releasing intrauterine system (levonorgestrel-IUS) with usual medical treatment in women with menorrhagia who presented to their primary
Tailored hydrogel microbeads of sodium carboxymethylcellulose as a carrier to deliver mefenamic acid: transmucosal administration
Shirizadeh B, et al.
Jundishapur journal of natural pharmaceutical products, 12(4) (2017)
Howard Horng et al.
Chemical research in toxicology, 26(3), 465-476 (2013-02-14)
Mefenamic acid, (MFA), a carboxylic acid-containing nonsteroidal anti-inflammatory drug (NSAID), is metabolized into the chemically reactive conjugates MFA-1-O-acyl-glucuronide (MFA-1-O-G) and MFA-S-acyl-CoA (MFA-CoA), which are both implicated in the formation of MFA-S-acyl-glutathione (MFA-GSH) conjugates, protein-adduct formation, and thus the potential toxicity
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