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M4267

Sigma-Aldrich

Mefenamic acid

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C15H15NO2
Número CAS:
61-68-7
Peso molecular:
241.29
Número CE:
200-513-1
Número MDL:
MFCD00051721
Código UNSPSC:
12161501
ID de substância PubChem:
24896815
NACRES:
NA.77

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originador

Shionogi

cadeia de caracteres SMILES

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)

chave InChI

HYYBABOKPJLUIN-UHFFFAOYSA-N

Informações sobre genes

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

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Aplicação

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)[1]
  • to test its neuroprotective functionality in zebrafish embryos/larvae[2]
  • in the preparation of mucoadhesive microparticles in hydrogel beads[3]

Ações bioquímicas/fisiológicas

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.[1] Contrarily, mefenamic acid elicits neuroprotection in in vivo ischemic stroke models by inhibiting cell toxicity induced by glutamate.[2] Mefenamic due its inhibitory effect on prostaglandin synthesis can be used in reducing edema and ache.[3]

Características e benefícios

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.

Pictogramas

Exclamation mark
GHS07

Palavra indicadora

Warning

Frases de perigo

H302

Classificações de perigo

Acute Tox. 4 Oral

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
MKCV5796
MKCW9195
MKCT3979
MKCM1927
MKCK7680

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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)
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
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
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
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