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Merck

M4267

Mefenamic acid

COX inhibitor

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
NACRES:
NA.77
PubChem Substance ID:
24896815
UNSPSC Code:
12161501
EC Number:
200-513-1
MDL number:
MFCD00051721
Quality level:
100

Key Documents

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Product Name

Mefenamic acid,

InChI key

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)

SMILES string

Cc1cccc(Nc2ccccc2C(O)=O)c1C

originator

Shionogi

Quality Level

100

Gene Information

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

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Application

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

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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

Substances Subject to be Indicated Names

ishl_indicated

Substances Subject to be Notified Names

ishl_notified

M4267-BULK: + M4267-50G: + M4267-100G: + M4267-VAR: + M4267-500G:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCM1927
MKCK7680
MKCK2055
MKCH3607
MKCB1870V

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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
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
S Kasichayanula et al.
Diabetes, obesity & metabolism, 15(3), 280-283 (2012-10-16)
Dapagliflozin is a selective sodium glucose cotransporter 2 (SGLT2) inhibitor that decreases serum glucose by reducing renal glucose reabsorption, thereby promoting urinary glucose excretion. Dapagliflozin is primarily metabolized via the uridine diphosphate-glucuronosyltransferase (UGT)1A9 pathway to its major inactive metabolite, dapagliflozin
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
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