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M1387

Sigma-Aldrich

4-Methylpyrazol -hydrochlorid

alcohol dehydrogenase inhibitor

Synonym(e):

Fomepizole

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About This Item

Empirische Formel (Hill-System):
C4H6N2 · HCl
CAS-Nummer:
56010-88-9
Molekulargewicht:
118.56
MDL-Nummer:
MFCD00012707
UNSPSC-Code:
12352202
PubChem Substanz-ID:
24278534
NACRES:
NA.77

Biologische Quelle

synthetic (organic)

Assay

≥95%

Form

powder

mp (Schmelzpunkt)

157-159  °C

Löslichkeit

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

Lagertemp.

2-8°C

SMILES String

Cl.Cc1cn[nH]c1

InChI

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

InChIKey

PUCXJHNDMYZOHG-UHFFFAOYSA-N

Angaben zum Gen

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

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Anwendung

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. Wirkung

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

Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves

Analysenzertifikate (COA)

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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
Kenneth E McMartin et al.
Clinical toxicology (Philadelphia, Pa.), 50(5), 375-383 (2012-05-05)
Fomepizole, a potent inhibitor of alcohol dehydrogenase, has replaced ethanol as antidote for methanol and ethylene glycol intoxications because of a longer duration of action and fewer adverse effects. Prior human studies have indicated that single doses of fomepizole are
Michael Levine et al.
Annals of emergency medicine, 59(6), 527-531 (2012-01-10)
Ethylene glycol remains an important toxic cause of metabolic acidosis and acute renal failure. Traditionally, inhibition of alcohol dehydrogenase along with hemodialysis has been used for treatment. Because of reported long elimination half-life of ethylene glycol during alcohol dehydrogenase inhibition
Paul G Thomes et al.
Autophagy, 9(1), 63-73 (2012-10-24)
Acute and chronic ethanol administration increase autophagic vacuole (i.e., autophagosome; AV) content in liver cells. This enhancement depends on ethanol oxidation. Here, we used parental (nonmetabolizing) and recombinant (ethanol-metabolizing) Hep G2 cells to identify the ethanol metabolite that causes AV
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