89-25-8 Usage
Description
Different sources of media describe the Description of 89-25-8 differently. You can refer to the following data:
1. 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.
2. 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
Different sources of media describe the Uses of 89-25-8 differently. You can refer to the following data:
1. 3-Methyl-1-phenyl-2-pyrazolin-5-one used as reagent for detection of reducing carbohydrates by ESI/MALDI -MS.
2. antioxidant, lipoxygenase inhibitor
3. 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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 89-25-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 9 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 89-25:
(4*8)+(3*9)+(2*2)+(1*5)=68
68 % 10 = 8
So 89-25-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-6H,7H2,1H3
89-25-8Relevant articles and documents
Structure and extractive ability of 1-alkyl- and 3-methyl-1-phenyl-2- pyrazolin-5-ones
Lesnov,Sazonova,Pavlov
, p. 298 - 302 (2005)
Extractive ability of 1-substituted 3-methylpyrazol-5-ones (LH) is studied. From acidic chloride complexes, ionic thallium(III) associates (LH 2)[TlCl4] are extracted; from trichloroacetate, coordination scandium complexes Sc(LH)4(CCl3COO) 3; and from ammine, copper(II) complexes CuL2. The extractive ability decreases in the order R = C7H15 > C6H13 > C5H11 > C 6H5 > C4H9. 2005 Pleiades Publishing, Inc.
Synthesis and Herbicidal Activity of 5-Heterocycloxy-3-methyl-1-substituted-1H-pyrazoles
Kang, Jing,Yue, Xia Li,Chen, Chang Shui,Li, Jian Hong,Ma, Hong Ju
, (2016)
With the objective of finding valuable herbicidal candidates, a series of new 5-heterocycloxy- 3-methyl-1-substituted-1H-pyrazoles were synthesized and their herbicidal activities were evaluated. The bioassay results showed that some compounds exhibited e
Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones
Wang, Rong-Hui,Li, Ya-Ling,He, Hong-Jiao,Xiao, You-Cai,Chen, Fen-Er
supporting information, p. 4302 - 4306 (2021/02/16)
The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.
Scale-Up of a Continuous Manufacturing Process of Edaravone
He, Yan,Hong, Qingxia,Mei, Wenliu,Sun, Tiemin,Wu, Chengjun,Zhou, Shuhao
, p. 2146 - 2153 (2021/09/13)
Edaravone belongs to a class of brain-protective agents, which can scavenge free radicals. To reduce impurities and improve the yield, a continuous flow production process of edaravone was developed. The synthesis is continuously carried out in two steps. The throughput can reach 11.328 kg/day and the purity of the final product is 99.95%, which are in accordance with the needs of production. This is an efficient and quick production process suitable for industrial production.