M1387
4-Methylpyrazole hydrochloride
alcohol dehydrogenase inhibitor
Synonym(s):
Fomepizole
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About This Item
Empirical Formula (Hill Notation):
C4H6N2 · HCl
CAS Number:
Molecular Weight:
118.56
NACRES:
NA.77
PubChem Substance ID:
MDL number:
UNSPSC Code:
12352100
InChI
1S/C4H6N2.ClH/c1-4-2-5-6-3-4;/h2-3H,1H3,(H,5,6);1H
SMILES string
Cl.Cc1cn[nH]c1
InChI key
PUCXJHNDMYZOHG-UHFFFAOYSA-N
biological source
synthetic (organic)
assay
≥95%
form
powder
mp
157-159 °C
solubility
methanol: 100 mg/mL, clear, colorless to yellow
storage temp.
2-8°C
Quality Level
Gene Information
human ... ADH1A(124), ADH1B(125), ADH1C(126)
Related Categories
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.
Biochem/physiol Actions
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
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
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
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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
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
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
Graham A Tipples et al.
Journal of clinical virology : the official publication of the Pan American Society for Clinical Virology, 30(3), 233-238 (2004-05-12)
Rubella virus generally causes a mild fever, rash illness similar in clinical presentation to infections by other viruses including measles and parvovirus B19. Rubella infections in pregnant women in the first trimester carry a high risk of congenital rubella syndrome
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