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222569

Sigma-Aldrich

Fomepizole

99%

Synonym(s):

4-Methylpyrazole

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About This Item

Empirical Formula (Hill Notation):
C4H6N2
CAS Number:
7554-65-6
Molecular Weight:
82.10
Beilstein:
105204
EC Number:
231-445-0
MDL number:
MFCD00005245
UNSPSC Code:
12352100
PubChem Substance ID:
24853343
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

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

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General description

4-Methylpyrazole inhibits CYP2E1 activity[1]. It also acts as alcohol dehydrogenase inhibitor[2].

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.[3]
  • A starting material for the synthesis of 4-methyl-3(5)-nitropyrazole by nitration.[4]
  • A ligand in the preparation of gallium(III) complex of 4-methylpyrazole as potential antitumor and antiviral agent.[5]

Useful as an antidote in methanol and ethylene glycol poisoning.

Biochem/physiol Actions

Alcohol dehydrogenase inhibitor
Alcohol dehydrogenase inhibitor.[6]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

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

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC3873V
BGBC2403V
BGBC0278V
BGBB4937V
BGBB4937

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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
Samjhana Thapaliya et al.
Autophagy, 10(4), 677-690 (2014-02-05)
Patients with alcoholic cirrhosis and hepatitis have severe muscle loss. Since ethanol impairs skeletal muscle protein synthesis but does not increase ubiquitin proteasome-mediated proteolysis, we investigated whether alcohol-induced autophagy contributes to muscle loss. Autophagy induction was studied in: A) Human
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
Mild Conditions for Copper-Catalysed N-Arylation of Pyrazoles
Cristau H-J, et al.
European Journal of Organic Chemistry, 2004(4), 695-709 (2004)
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