Edaravone

Base Information

• Chemical Name: Edaravone
• CAS No.: 89-25-8
• Deprecated CAS: 115566-83-1,12235-58-4,206195-95-1,52224-17-6,62495-97-0,72134-66-8,12235-58-4,206195-95-1,52224-17-6,62495-97-0,72134-66-8
• Molecular Formula: C10H10N2O
• Molecular Weight: 174.202
• Hs Code.: 2933.19
• European Community (EC) Number: 201-891-0
• NSC Number: 758622,26139,2629,12
• UNII: S798V6YJRP
• DSSTox Substance ID: DTXSID9021130
• Nikkaji Number: J37.341I
• Wikipedia: Edaravone
• Wikidata: Q335099
• NCI Thesaurus Code: C74323
• RXCUI: 1921877
• Metabolomics Workbench ID: 54417
• ChEMBL ID: CHEMBL290916
• Mol file: 89-25-8.mol

Synonyms:1 Phenyl 3 methyl 5 pyrazolone;1-phenyl-3-methyl-5-pyrazolone;3 Methyl 1 phenyl 2 pyrazolin 5 one;3-methyl-1-phenyl-2-pyrazolin-5-one;edarabone;edaravone;MCI 186;MCI-186;MCI186;norantipyrine;norphenazone;phenylmethylpyrazolone;Radicava

Chemical Property of Edaravone

Chemical Property:

• Appearance/Colour: Off white to light yellow powder
• Vapor Pressure: 0.000141mmHg at 25°C
• Melting Point: 126-128 °C(lit.)
• Refractive Index: 1.606
• Boiling Point: 333 °C at 760 mmHg
• PKA: 2.73±0.50(Predicted)
• Flash Point: 155.2 °C
• PSA: 32.67000
• Density: 1.17 g/cm³
• LogP: 1.29980
• Storage Temp.: Store at RT
• Solubility.: 3.30g/l
• Water Solubility.: 3 g/L (20 ºC)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 174.079312947
• Heavy Atom Count: 13
• Complexity: 241

Purity/Quality:

99% ^*data from raw suppliers

Edaravone ≥99%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrazoles
• Drug Classes: Amyotrophic Lateral Sclerosis Agents
• Canonical SMILES: CC1=NN(C(=O)C1)C2=CC=CC=C2
• Recent ClinicalTrials: PK Study in Subjects With Severe Hepatic Impairment
• Recent EU Clinical Trials: A multicenter, open-label extension study to investigate the long-term safety of FAB122 in patients with Amyotrophic Lateral Sclerosis
• Recent NIPH Clinical Trials: Efficacy and Safety Extension Study of Oral Edaravone Administered in Subjects With ALS
• 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. 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.
• Uses: 3-Methyl-1-phenyl-2-pyrazolin-5-one used as reagent for detection of reducing carbohydrates by ESI/MALDI -MS. antioxidant, lipoxygenase inhibitor Edaravone inhibits the disease activity in rheumatoid arthritis.

Technology Process of Edaravone

There total 97 articles about Edaravone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

acetoacetic acid methyl ester (105-45-3) + phenylhydrazine (100-63-0) → edaravone (89-25-8)

Guidance literature:

With acetic acid; for 3h; Reflux;

DOI:10.1016/j.tetlet.2012.05.148

Reference yield: 93.0%

4-methyleneoxetan-2-one (674-82-8,2130-41-8) + phenylhydrazine (100-63-0) → edaravone (89-25-8)

Guidance literature:

4-methyleneoxetan-2-one; With ammonium hydroxide; at 10 ℃; for 0.5h;

phenylhydrazine; at 60 ℃; for 2h;

With hydrogenchloride; In water; for 1h; pH=5;

Reference yield: 92.0%

5-methyl-2-phenylpyrazolidin-3-one (13292-56-3) → edaravone (89-25-8)

Guidance literature:

With sodium anthraquinone-2-sulfonate; palladium diacetate; potassium carbonate; In chlorobenzene; at 110 ℃; for 6h; Reagent/catalyst;

DOI:10.1016/j.tetlet.2019.03.063

upstream raw materials:

ethyl 3-(2-phenylhydrazono)butanoate

(5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-3-yl)-acetic acid

3,4-dimethyl-1-phenyl-1H,6H-pyrano<2,3-c>pyrazol-6-one

acetic acid

Downstream raw materials:

5-methoxy-3-methyl-1-phenyl-1H-pyrazole

5,5'-dimethyl-2,2'-diphenyl-2,4-dihydro-2'H-[3,4']bipyrazolyliden-3'-one

3-methyl-1-phenyl-4-furfurylidene-5-pyrazolone

5-methyl-4-[(3-methyl-3H-benzoxazol-2-yliden)-ethylidene]-2-phenyl-2,4-dihydro-pyrazol-3-one

Refernces

• 1、 Xu, Cun-Jin,Shi, Yan-Qin. "Synthesis and crystal structure of 5-chloro-3-methyl-1-phenyl-1H-pyrazole- 4-carbaldehyde". . p. 1816 - 1819. Retrieved 2011.
• 2、 Nidhar, Manisha,Khanam, Shaziya,Sonker, Priyanka,Gupta, Priya,Mahapatra, Archisman,Patil, Swaraj,Yadav, Brijesh Kumar,Singh, Rahul Kumar,Kumar Tewari, Ashish. "Click inspired novel pyrazole-triazole-persulfonimide & pyrazole-triazole-aryl derivatives; Design, synthesis, DPP-4 inhibitor with potential anti-diabetic agents". supporting information. . Retrieved 2022/01/22.
• 3、 Wang, Rong-Hui,Li, Ya-Ling,He, Hong-Jiao,Xiao, You-Cai,Chen, Fen-Er. "Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones". supporting information. p. 4302 - 4306. Retrieved 2021/02/16.