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Key Documents

222569

Sigma-Aldrich

Fomepizole

99%

Synonym(s):

4-Methylpyrazole

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About This Item

Empirical Formula (Hill Notation):
C4H6N2
CAS Number:
Molecular Weight:
82.10
Beilstein:
105204
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

refractive index

n20/D 1.495 (lit.)

bp

99-100 °C/6 mmHg (lit.)

solubility

alcohol: soluble(lit.)
water: soluble(lit.)

density

0.993 g/mL at 25 °C (lit.)

SMILES string

Cc1cn[nH]c1

InChI

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

InChI key

RIKMMFOAQPJVMX-UHFFFAOYSA-N

Gene Information

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General description

4-Methylpyrazole inhibits CYP2E1 activity. It also acts as alcohol dehydrogenase inhibitor.

Application

Fomepizole (4-Methylpyrazole) can be used as:
  • A reactant to prepare 4-methyl-1-phenyl-1H-pyrazole by reacting with bromobenzene via N-arylation using a copper catalyst.
  • A starting material for the synthesis of 4-methyl-3(5)-nitropyrazole by nitration.
  • A ligand in the preparation of gallium(III) complex of 4-methylpyrazole as potential antitumor and antiviral agent.

Useful as an antidote in methanol and ethylene glycol poisoning.

Biochem/physiol Actions

Alcohol dehydrogenase inhibitor
Alcohol dehydrogenase inhibitor.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

204.8 °F - closed cup

Flash Point(C)

96 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Synthesis and characterization of potential antitumour and antiviral gallium (III) complexes of N-heterocycles
Kratz F, et al.
Polyhedron, 11(4), 487-498 (1992)
Jafar Shahraki et al.
Iranian journal of pharmaceutical research : IJPR, 12(4), 829-844 (2014-02-14)
In this research, we investigated the cytotoxic mechanisms of Cochlodinium polykrikoidescell lysate on isolated rat liver hepatocytes.This micro algae is responsible for a severe and widespread harmful algal bloom in the Persian Gulf and Gulf of Oman (2008-2009). Isolated hepatocytes
Marisa Battistella
The Annals of pharmacotherapy, 36(6), 1085-1089 (2002-05-23)
To assess the use of fomepizole in the treatment of ethylene glycol poisoning in the absence of hemodialysis. A MEDLINE search (1966-May 2001) of English-language literature pertaining to the use of fomepizole in ethylene glycol poisoning was performed. Key search
Amanda M Barkley-Levenson et al.
Brain sciences, 11(1) (2021-01-23)
Central nervous system (CNS) hyperexcitability is a clinically significant feature of acute ethanol withdrawal. There is evidence for a genetic contribution to withdrawal severity, but specific genetic risk factors have not been identified. The gene glyoxalase 1 (Glo1) has been
J Samuelson et al.
Archives of medical research, 23(2), 31-33 (1992-01-01)
Ethanol is the major metabolic product of glucose fermentation by the protozoan parasite E. histolytica under the anaerobic conditions found in the lumen of the colon. With the goal of finding new targets for anti-amebic drugs, the E. histolytica NADP(+)-dependent

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