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M1387

Sigma-Aldrich

4-Methylpyrazole hydrochloride

alcohol dehydrogenase inhibitor

Synonyme(s) :

Fomepizole

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About This Item

Formule empirique (notation de Hill):
C4H6N2 · HCl
Numéro CAS:
56010-88-9
Poids moléculaire :
118.56
Numéro MDL:
MFCD00012707
Code UNSPSC :
12352202
ID de substance PubChem :
24278534
Nomenclature NACRES :
NA.77

Source biologique

synthetic (organic)

Pureté

≥95%

Forme

powder

Pf

157-159  °C

Solubilité

methanol: 100 mg/mL, clear, colorless to yellow

Température de stockage

2-8°C

Chaîne SMILES 

Cl.Cc1cn[nH]c1

InChI

1S/C4H6N2.ClH/c1-4-2-5-6-3-4;/h2-3H,1H3,(H,5,6);1H

Clé InChI

PUCXJHNDMYZOHG-UHFFFAOYSA-N

Informations sur le gène

human ... ADH1A(124) , ADH1B(125) , ADH1C(126)

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Application

4-Methylpyrazole hydrochloride has been used:
  • as a cytochrome P450 2E1 inhibitor
  • as cytochrome P450 2E1 and alcohol dehydrogenase inhibitor in 1C11 neural progenitor cells
  • to inhibit ethanol oxidation in VL-17A cells expressing alcohol dehydrogenase and HepG2 cells

Useful as an antidote in methanol and ethylene glycol poisoning.

Actions biochimiques/physiologiques

4-Methylpyrazole (4MP) inhibits ethanol oxidation in liver microsomes. It also blocks the c-Jun N-terminal kinase (JNK) activation in in vitro liver injury models.
Alcohol dehydrogenase inhibitor

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Trang T T Nguyen et al.
Critical reviews in immunology, 36(2), 163-177 (2016-12-03)
Most serum immunoglobulin M (IgM) is "natural IgM", which is produced apparently spontaneously by a distinct subset of B cells requiring no exogenous antigenic or microbial stimuli. Natural IgM is an evolutionarily conserved molecule and reacts with a variety of
Rachael Racine et al.
Immunology letters, 125(2), 79-85 (2009-06-23)
Much has been learned about the structure, function, and production of IgM, since the antibody's initial characterization. It is widely accepted that IgM provides a first line of defense during microbial infections, prior to the generation of adaptive, high-affinity IgG
Irina Bancos et al.
PloS one, 8(2), e56827-e56827 (2013-03-02)
Classical tumor suppressor genes block neoplasia by regulating cell growth and death. A remarkable puzzle is therefore presented by familial paraganglioma (PGL), a neuroendocrine cancer where the tumor suppressor genes encode subunits of succinate dehydrogenase (SDH), an enzyme of the
Katherine J Lepik et al.
Clinical toxicology (Philadelphia, Pa.), 49(5), 391-401 (2011-07-12)
Little is known about medication errors which occur with the antidotes ethanol and fomepizole, used for treatment of methanol and ethylene glycol poisoning. Study objectives were to describe and compare the frequency, type, outcome and underlying causes of medication errors
D E Feierman et al.
The Biochemical journal, 239(3), 671-677 (1986-11-01)
Pyrazole and 4-methylpyrazole, which are inhibitors of alcohol dehydrogenase, were also found to be effective inhibitors of the oxidation of ethanol by liver microsomes (microsomal fractions) in vitro. Ethanol oxidation by microsomes from rats previously treated for 2 or 3
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