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| | 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Basic information |
| | 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Chemical Properties |
| Melting point | 126-128 °C(lit.) | | Boiling point | 287 °C265 mm Hg(lit.) | | density | 1,12 g/cm3 | | vapor pressure | 0.016Pa at 20℃ | | refractive index | 1.6300 (estimate) | | Fp | 191°C/17mm | | storage temp. | 2-8°C | | solubility | 3.30g/l | | pka | 2.73±0.50(Predicted) | | form | Crystalline Powder | | color | Yellow to beige | | PH | 4.0-4.4 (H2O, 20℃)(saturated aqueous solution) | | Water Solubility | 3 g/L (20 ºC) | | Merck | 14,6713 | | BRN | 609575 | | Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. | | InChIKey | QELUYTUMUWHWMC-UHFFFAOYSA-N | | LogP | 0.75 at 24℃ | | CAS DataBase Reference | 89-25-8(CAS DataBase Reference) | | NIST Chemistry Reference | 3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-2-phenyl-(89-25-8) | | EPA Substance Registry System | 1-Phenyl-3-methyl-5-pyrazolone (89-25-8) |
| | 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Usage And Synthesis |
| Description | Edaravone was marketed in Japan for improving neurologic recovery
following acute brain infarction. Currently, several agents classified as neuroprotectants
and acting by diverse mechanisms (inhibition of glutamate release, blockade of calcium
channels, lazaroids) have been marketed for treating the outcomes of brain damage due to
trauma, ischemia or cardiac arrest. Edavarone is the first antioxidant with free radical
scavenging activity to be introduced for this pathology. This previously described molecule
(in particular as norantipyrine, one of three metabolites of antipyrine in mammals) can be
simply prepared by direct cyclization of phenylhydrazine with alkylacetoacetate. Edarevone
is a lipophilic agent, readily accessible to brain tissue, that is capable of reducing edema
in the brain following ischemia by blocking the arachidonic acid cascade triggering
peroxidative neurodegeneration. Interestingly, this agent has been shown to quench active
oxygen species in endothelial cell homogenate, as well as inhibiting in vitro lipid peroxidative disintegration of membranes, so making this compound effective during
reperfusion following ischemic injury. As an additional indication, phase III trials started with edaravone for increasing the chance of recovery after subarachnoid hemorrhage. | | Description | MCI-186 is a free radical scavenger with diverse protective effects in vivo. Most notably, it reduces damage due to ischemia-reperfusion injury in lung, liver, and brain in animal models of transplant, infection, traumatic brain injury, and stroke. MCI-186 provides these protective effects, at least in part, by reducing reactive oxygen species, inhibiting apoptosis, and blocking nonenzymatic peroxidation and lipoxygenase activity. | | Chemical Properties | Off white to light yellow powder | | Originator | Mitsubishi Pharma (Japan) | | Uses | 3-Methyl-1-phenyl-2-pyrazolin-5-one used as reagent for detection of reducing carbohydrates by ESI/MALDI -MS. | | Uses | antioxidant, lipoxygenase inhibitor | | Uses | Edaravone inhibits the disease activity in rheumatoid arthritis. | | Definition | ChEBI: A pyrazolone that is 2,4-dihydro-3H-pyrazol-3-one which is substituted at positions 2 and 5 by phenyl and methyl groups, respectively. | | Brand name | Radicut | | General Description | A free radical scavenger and antioxidant that reduces post-ischemic brain injury. Inhibits iron-dependent peroxidation in rat brain homogenates (IC50 = 15 μM). Inhibits mitochondrial permeability transition pore. | | Hazard | Toxic by ingestion. | | Flammability and Explosibility | Notclassified | | Biological Activity | A radical scavenger and antioxidant which is able to protect against the effects of ischemia, probably by inhibiting the lipoxygenase system. Protects against MPTP-induced neurotoxicity. | | Biochem/physiol Actions | Product does not compete with ATP. | | Safety Profile | Moderately toxic by ingestion andintraperitoneal routes. An eye irritant. When heated todecomposition it emits toxic fumes of NOx. | | storage | Store at RT | | Purification Methods | Crystallise the pyrazolone from hot H2O, EtOH or EtOH/water (1:1). It complexes with metals. [Veibel et al. Acta Chim Scand 6 1066 1952, Beilstein 24 II 9, 24 III/IV 71.] | | References | 1) Watanabe et al. (1994), Protective effects of MCI-186 on cerebral ischemia:possible involvement of free radical scavenging and antioxidant actions; J. Pharmacol. Exp. Ther., 268 1597
2) Yoshida et al. (2006) Neuroprotective effects of edaravone:a novel free radical scavenger in cerebrovascular injury; CNS Drug Reviews, 12 9
3) Kawasaki et al. (2007) Edaravone (3-Methyl-1-phenyl-2-pyrazolin-5-one), a Radical Scavenger, Prevents 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced Neurotoxicity in the Substantia Nigra but Not the Striatum; J. Pharmacol. Exp. Ther., 322 274 |
| | 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one Preparation Products And Raw materials |
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