4-Methylpyrazole - CAS 7554-65-6
Not Intended for Therapeutic Use. For research use only.
Category:
Inhibitor
Product Name:
4-Methylpyrazole
Catalog Number:
7554-65-6
Synonyms:
1H-Pyrazole, 4-methyl-;4-Methyl-1H-pyrazole;Fomepizole;Antizol;Fomepizol
CAS Number:
7554-65-6
Description:
4-Methylpyrazole is a competitive inhibitor of alcohol dehydrogenase, which catalyzes metabolism of ethylene glycol and methanol to toxic metabolites. It is used as an antidote for ethylene glycol or methanol poisoning. It may be used alone or in combination with hemodialysis. It can prevent the formation of toxic alcohol metabolites that generate metabolic acidosis at 10 µM in monkeys. It also inhibits CYP2E1 activity. It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.
Molecular Weight:
82.10
Molecular Formula:
C4H6N2
Quantity:
Kilogram to ton
Quality Standard:
In-house standard
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CC1=CNN=C1
InChI:
InChI=1S/C4H6N2/c1-4-2-5-6-3-4/h2-3H,1H3,(H,5,6)
InChIKey:
RIKMMFOAQPJVMX-UHFFFAOYSA-N
Targets:
Others
Chemical Structure
CAS 7554-65-6 4-Methylpyrazole

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Reference Reading


1.Ethanol and Acetaldehyde After Intraperitoneal Administration to Aldh2-Knockout Mice-Reflection in Blood and Brain Levels.
Jamal M1, Ameno K2, Tanaka N2, Ito A2, Takakura A2, Kumihashi M2, Kinoshita H2. Neurochem Res. 2015 Dec 8. [Epub ahead of print]
This paper reports, for the first time, on the analysis of ethanol (EtOH) and acetaldehyde (AcH) concentrations in the blood and brains of Aldh2-knockout (Aldh2-KO) and C57B6/6J (WT) mice. Animals were administrated EtOH (1.0, 2.0 or 4.0 g/kg) or 4-methylpyrazole (4-MP, 82 mg/kg) plus AcH (50, 100 or 200 mg/kg) intraperitoneally. During the blood tests, samples from the orbital sinus of the eye were collected. During the brain tests, dialysates were collected every 5 min (equal to a 15 µl sample) from the striatum using in vivo brain microdialysis. Samples were collected at 5, 10, 15, 20, 25, 30 and 60 min intervals post-EtOH and -AcH injection, and then analyzed by head-space GC. In the EtOH groups, high AcH levels were found in the blood and brains of Aldh2-KO mice, while only small traces of AcH were seen in the blood and brains of WT mice. No significant differences in EtOH levels were observed between the WT and the Aldh2-KO mice for either the EtOH dose.
2.Methanol Kinetics in Chronic Kidney Disease After Fomepizole: A Case Report.
Maskell KF1, Beckett S, Cumpston KL. Am J Ther. 2015 Dec 9. [Epub ahead of print]
Methanol is a common toxicant in the United States, especially from automotive products. Its kinetics have been described previously and typically involve little urinary excretion. We present a case of prolonged methanol half-life in a patient with chronic kidney disease. An 80-year-old male with a baseline glomerular filtration rate of 24 mL·min·1.73 m was transferred to our facility after unintentional methanol ingestion. The original facility had treated him with an oral ethanol load; upon arrival to our facility, he was immediately loaded with fomepizole. His initial serum methanol concentration was 66.1 mg/dL. After a risk/benefit discussion, we decided not to perform hemodialysis on the patient and he was treated with fomepizole and supportive care. After 6 days as an inpatient, the patient's methanol level had declined to 22 mg/dL, fomepizole was discontinued, and the patient was able to be discharged without apparent complications.
3.Mind the gap: a case of severe methanol intoxication.
Nazir S1, Melnick S1, Ansari S1, Kanneh HT2. BMJ Case Rep. 2016 Feb 25;2016. pii: bcr2015214272. doi: 10.1136/bcr-2015-214272.
We report a case of a 37-year-old woman with non-insulin-dependent diabetes on sitagliptin, an alcohol abuser who was brought unresponsive to the emergency department of our hospital. On arrival, the patient was intubated and mechanically ventilated due to a low Glasgow Coma score of 3/15. Initial laboratory testing identified profound high anion gap metabolic acidosis. Owing to the dubious circumstances and the depth of acidosis, methanol and ethylene glycol intoxication was suspected. Further evaluation revealed a significantly increased serum osmolal gap. Pending volatile compound screen, fomepizole was started and urgent haemodialysis undertaken. Subsequent brain MRI identified changes in putamen of bilateral basal ganglia, suggestive of methanol intoxication. The patient was later found to have an initial methanol level of 237 mg/dL. She was successfully extubated on day 2 of hospitalisation, with residual cognitive and visual deficits.
4.[Antidote update].
Kiyota K. Nihon Rinsho. 2016 Feb;74(2):236-40.
In Japan, several products of the antidote for poisoning have been authorized in clinical use from some recent years. For example, Hydroxcobalamin for cyanide poisoning was introduced in 2008. In 2009, Ministry of Health, Labour and Welfare invited suggestions of demand of pharmaceutical products which is high in the need in the medical care but yet unauthorized. Japanese Society for Clinical Toxicology and Japan Poison Information Center applied some candidates including methyleneblue (MB) and fomepizole, both of them were authorized in clinical market in 2015. MB is the medicine for methemoglobinemia, caused by variety of chemical products such as nitrogen oxide. Fomepizole is the antidote for methanol and ethyleneglycol, blocking alcohol dehydrogenase.