| Identification | More | [Name]
4-Methylpyrazole | [CAS]
7554-65-6 | [Synonyms]
4-METHYLPYRAZOLE
4-METHYLPYRRAZOLE
AKOS B014452
ART-CHEM-BB B014452
fomepizol
FOMEPIZOLE
1H-Pyrazole, 4-methyl-
4-Methyl-1H-pyrazole
4-Methylpyrazol
4-methyl-pyrazol
Pyrazole, 4-methyl-
4-METHYLPYRAZOLE FREE BASE
Fomepizolefreebase
4-Methylpyrazole,98%
4-Methylpyrazole, 97+%
4-Methyl-1H-pyrazole, 97+% | [EINECS(EC#)]
231-445-0 | [Molecular Formula]
C4H6N2 | [MDL Number]
MFCD00005245 | [Molecular Weight]
82.1 | [MOL File]
7554-65-6.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colourless to yellowish liquid after melting | [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 ]
n20/D 1.495(lit.)
| [Fp ]
205 °F
| [storage temp. ]
2-8°C | [solubility ]
soluble | [form ]
Liquid After Melting | [pka]
14.95±0.50(Predicted) | [color ]
Clear colorless to yellow | [Specific Gravity]
0.993 | [Water Solubility ]
soluble | [Sensitive ]
Hygroscopic | [Detection Methods]
GC | [Merck ]
14,4216 | [BRN ]
105204 | [LogP]
1.097 (est) | [CAS DataBase Reference]
7554-65-6(CAS DataBase Reference) | [NIST Chemistry Reference]
4-methylpyrazole(7554-65-6) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
2810 | [WGK Germany ]
3
| [RTECS ]
UQ7350000
| [F ]
10-23 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29331990 | [Toxicity]
LD50 (7 days) in mice, rats (mmol/kg): 3.8, 3.8 i.v.; 7.8, 6.5 orally (Magnusson) |
| Hazard Information | Back Directory | [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.
| [Chemical Properties]
clear colourless to yellowish liquid after melting | [Originator]
Orphan Medical (US) | [Uses]
Antidote in methanol or ethylene glycol poisoning;Alcohol dehydrogenase inhibitor | [Uses]
antidote to ethylene glycol or methanol poisoning | [Uses]
Useful as an antidote in methanol and ethylene glycol poisoning. | [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. |
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