4-Methylpyrazole
Synonym(s):4-Methylpyrazole
- CAS NO.:7554-65-6
- Empirical Formula: C4H6N2
- Molecular Weight: 82.1
- MDL number: MFCD00005245
- EINECS: 231-445-0
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-19 23:02:33
What is 4-Methylpyrazole?
Absorption
Rapid and complete
Toxicity
Headache, nausea, dizziness
Description
Fomepizole is the first drug indicated as an antidote for ethylene glycol poisoning (it has also shown promise as a treatment for methanol poisoning). Fomepizole is 4-methyl-1H-pyrazole active as a synthetic alcohol dehydrogenase inhibitor, blocking the formation of toxic ethylene glycol metabolites which are responsible for a severe metabolic acidosis and renal failure. In limited human studies, it reversed the toxicity of potentially lethal doses of ethylene glycol. The main urinary metabolite has been reported to be 4-carboxypyrazole by oxidation of the methyl group. Compared with the current treatment (ethanol), the duration of action is longer and the safety is improved, with no toxic effects reported.
Description
Fomepizole is a competitive inhibitor of alcohol dehydrogenase, the enzyme that catalyzes metabolism of ethylene glycol and methanol to toxic metabolites. At 10 μM in monkeys, it can prevent the formation of toxic alcohol metabolites that generate metabolic acidosis. This compound is typically used as an antidote for ethylene glycol or methanol poisoning.
Chemical properties
clear colourless to yellowish liquid after melting
Originator
Orphan Medical (US)
The Uses of 4-Methylpyrazole
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.
The Uses of 4-Methylpyrazole
Useful as an antidote in methanol and ethylene glycol poisoning.
The Uses of 4-Methylpyrazole
Antidote in methanol or ethylene glycol poisoning;Alcohol dehydrogenase inhibitor
The Uses of 4-Methylpyrazole
antidote to ethylene glycol or methanol poisoning
Background
Fomepizole is used as an antidote in confirmed or suspected methanol or ethylene glycol poisoning. Fomepizole is a competitive inhibitor of alcohol dehydrogenase, the enzyme that catalyzes the initial steps in the metabolism of ethylene glycol and methanol to their toxic metabolites.
Indications
Antizol is indicated as an antidote for ethylene glycol (such as antifreeze) or methanol poisoning, or for use in suspected ethylene glycol or methanol ingestion, either alone or in combination with hemodialysis
What are the applications of Application
Fomepizole is an alcohol dehydrogenase inhibitor
Definition
ChEBI: A member of the class of pyrazoles that is 1H-pyrazole substituted by a methyl group at position 4.
Manufacturing Process
Preparation of 4-methylpyrazole
1.0 g (6.67 mmol) of sodium iodide is added to a suspension of 560 g (4.0
mol) of 70% strength sulfuric acid and 62.5 g (1.0 mol) of 80% strength
hydrazine hydrate and, at 125°C, 86.4 g (1.2 mol) of isobutyraldehyde are
pumped under the surface of the suspension over the course of 2 hours using
a metering pump. During and up to 100 min after the addition of
isobutyraldehyde, a total of 175 g of water was distilled out, with the
temperature of the mixture rising to 135°C. The solution is cooled and
adjusted to pH 8.6 with 820 g (5.125 mol) of 25% strength sodium
isobutyraldehyde hydroxide solution and is extracted with isobutanol. The
combined extracts are concentrated to 82 g in a rotary evaporator and then
distilled. The main fraction (boiling point 82°C/7 mbar; 49 g) consists of 82%
4-methylpyrazole. Yield: 49% of theory.
brand name
Antizol (Jazz).
Therapeutic Function
Antidote
General Description
4-Methylpyrazole inhibits CYP2E1 activity. It also acts as alcohol dehydrogenase inhibitor.
Biochem/physiol Actions
Alcohol dehydrogenase inhibitor.
Pharmacokinetics
Fomepizole is a competitive inhibitor of alcohol dehydrogenase, the enzyme that catalyzes the initial steps in the metabolism of ethylene glycol and methanol to their toxic metabolites. Ethylene glycol is first metabolized to glycoaldehyde which then undergoes further oxidation to glycolate, glyoxylate, and oxalate. Glycolate and oxalate are primarily responsible for metabolic acidosis and renal damage seen in ethylene glycol toxicity. {01}{03} Methanol is first metabolized to formaldehyde and then undergoes subsequent oxidation via formaldehyde dehydrogenase to become formic acid. It is formic acid that is primarily responsible for the metabolic acidosis and visual disturbances that are associated with methanol poisoning.
Metabolism
Primarily hepatic. the primary metabolite is 4-carboxypyrazole (approximately 80 to 85% of an administered dose). Minor metabolites include 4-hydroxymethylpyrazole and the N -glucuronide conjugates of 4-carboxypyrazole and 4-hydroxymethylpyrazole.
Properties of 4-Methylpyrazole
Melting point: | 13°C |
Boiling point: | 99-100 °C6 mm Hg(lit.) |
Density | 0.993 g/mL at 25 °C(lit.) |
vapor pressure | 7.136-87.85Pa at 20-50℃ |
refractive index | n |
Flash point: | 205 °F |
storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
solubility | soluble |
form | Liquid After Melting |
pka | 14.95±0.50(Predicted) |
Specific Gravity | 0.993 |
color | Clear colorless to yellow |
Water Solubility | soluble |
Sensitive | Hygroscopic |
Merck | 14,4226 |
BRN | 105204 |
CAS DataBase Reference | 7554-65-6(CAS DataBase Reference) |
NIST Chemistry Reference | 4-methylpyrazole(7554-65-6) |
Safety information for 4-Methylpyrazole
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 4-Methylpyrazole
Abamectin manufacturer
Apothecon Pharmaceuticals Pvt Ltd
Inventys Research Company Pvt Ltd
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