4-methyl-1H-pyrazole

• ChemBase ID: 1083
• Molecular Formular: C4H6N2
• Molecular Mass: 82.10384
• Monoisotopic Mass: 82.0530982
• SMILES: [nH]1ncc(c1)C
• Canonical SMILES: Cc1c[nH]nc1
• InChI: InChI=1S/C4H6N2/c1-4-2-5-6-3-4/h2-3H,1H3,(H,5,6)
• InChIKey: RIKMMFOAQPJVMX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-methyl-1H-pyrazole
• IUPAC Traditional name: fomepizole
• Brand Name: Antizol
• Synonyms: Fomepizole; 4-Methyl-1H-pyrazole; 4-methylpyrazole; Fomepizol [INN-Spanish]; Fomepizole [USAN:INN]; Fomepizolum [INN-Latin]; Fomepizole; Fomepizole; 4-METHYLPYRAZOLE; 4-Methyl-1H-pyrazole; 4-甲基吡唑; 4-甲基吡唑; 甲吡唑

Database IDs

• CAS Number: 7554-65-6
• EC Number: 231-445-0
• MDL Number: MFCD00005245
• Beilstein Number: 105204
• Merck Index: 144216
• PubChem SID: 24885875; 46508566; 160964546; 24853343
• PubChem CID: 3406
• CHEBI ID: 5141
• ATC CODE: V03AB34
• CHEMBL: 1308
• Chemspider ID: 3289
• DrugBank ID: DB01213
• KEGG ID: D00707
• Unique Ingredient Identifier: 83LCM6L2BY
• Wikipedia Title: Fomepizole

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.820059
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 0.7906679
• LogD (pH = 7.4): 0.7908489
• Log P: 0.7908512
• Molar Refractivity: 24.7866 cm^3
• Polarizability: 8.897982 Å^3
• Polar Surface Area: 28.68 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.41
• LOG S: 0.83
• Solubility (Water): 5.59e+02 g/l

PROPERTIES

Physical Property

• Melting Point: 13°C
• Boiling Point: 204-207 °C (97,3 kPa); 204-207°C; 99-100 °C/6 mmHg(lit.)
• Flash Point: 204.8 °F; 96 °C; 96.0 °C; 96°C(204°F)
• Density: 0.99 g/cm^3; 0.99 g/ml; 0.993 g/mL at 25 °C(lit.); 1.018
• Refractive Index: 1.4945; n20/D 1.495; n20/D 1.495(lit.)
• Hydrophobicity(logP): 0.51; 0.9

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Hygroscopic; IRRITANT
• RTECS: UQ7350000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; R:22-36/37/38
• Safety Statements: 26-36; 26-36/37; S:25-26-36/37/39
• TSCA Listed: false; 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335; H302-H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ADH1A(124), ADH1B(125), ADH1C(126)

Product Information

• Purity: ≥97.0% (GC); 95%; 97%; 97+%; 98%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C4H6N2

DETAILS

MP Biomedicals - 02155648

Free Base 1 ml = approx. 0.99 g

DrugBank - DB01213

• Drug Groups: approved
• Description: 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.
• Indication: 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
• Pharmacology: 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. It is glycolate and oxalate that are primarily responsible for the metabolic acidosis and renal damage that are seen in ethylene glycol poisoning. {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.
• Toxicity: Headache, nausea, dizziness
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepaticm the primary metabolite is 4-carboxypyrazole (approximately 80 to 85% of an administered dose). Other metabolites include 4-hydroxymethylpyrazole and the N -glucuronide conjugates of 4-carboxypyrazole and 4-hydroxymethylpyrazole.
• Absorption: Rapid and complete
• Half Life: The plasma half-life of Antizol varies with dose, even in patients with normal renal function, and has not been calculated.
• Elimination: In healthy volunteers, only 1-3.5% of the administered dose of Antizol? (7-20 mg/kg oral and IV) was excreted unchanged in the urine, indicating that metabolism is the major route of elimination. In humans, the primary metabolite of Antizol? is 4-carboxypyrazole (approximately 80-85% of administered dose), which is excreted in the urine. The metabolites of Antizol? are excreted renally.
• Distribution: * 0.6 to 1.02 L/kg
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - M9888

Application
Useful as an antidote in methanol and ethylene glycol poisoning.
Biochem/physiol Actions
Alcohol dehydrogenase inhibitor

Sigma Aldrich - 222569

Application
Useful as an antidote in methanol and ethylene glycol poisoning.
Alcohol dehydrogenase inhibitor.1
Biochem/physiol Actions
Alcohol dehydrogenase inhibitor
Packaging
1, 5 g in glass bottle

Sigma Aldrich - 69020

Application
Useful as an antidote in methanol and ethylene glycol poisoning.
Biochem/physiol Actions
Alcohol dehydrogenase inhibitor
Other Notes
Inhibitor of alcohol dehydrogenase1