W1P

5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one


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Chemical Component Summary

Name5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
Identifiers5-methyl-2-phenyl-4~{H}-pyrazol-3-one
FormulaC10 H10 N2 O
Molecular Weight174.199
TypeNON-POLYMER
Isomeric SMILESCC1=NN(C(=O)C1)c2ccccc2
InChIInChI=1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-6H,7H2,1H3
InChIKeyQELUYTUMUWHWMC-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count23
Chiral Atom Count0
Bond Count24
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB12243 
NameEdaravone
Groups
  • approved
  • investigational
DescriptionEdaravone is a free radical scavenger and neuroprotective agent with antioxidant properties.[A254257] It has three tautomers.[A19140] Edaravone works to scavenge reactive oxygen species, which have been implicated in neurological disorders, such as amyotrophic lateral sclerosis (ALS) and cerebral ischemia.[A19140,L44007,A254257] The intravenous formulation of edaravone was first approved in Japan in 2001 for the treatment of acute ischemic stroke.[L44007] It was later approved for the treatment of amyotrophic lateral sclerosis (ALS) in Japan and South Korea in 2015, followed by the FDA approval in May 2017 [L41810] and Health Canada approval in October 2018.[L44007] The oral suspension formulation of edaravone was approved by the FDA in May 2022 and by Health Canada in November 2022.[L44017] Edaravone was initially granted orphan designation by the European Medicines Agency on June 19, 2015 [L44007] and was under regulatory review in Europe. However, the drug manufacturer, Mitsubishi Tanabe Pharma, withdrew the Marketing Authorization Application (MAA) for edaravone from the European market on May 24, 2019, in response to the request made by the Committee for Medicinal Products for Human Use (CHMP) for a long-term study demonstrating the long-term efficacy and safety of edaravone.[L44002,L44012] Edaravone was also investigated in other disorders, such as Alzheimer's disease,[A19138] neuropathic pain, and ischemia-induced nerve injury.[A19139]
Synonyms
  • Phenyl methyl pyrazolone
  • 3-methyl-1-phenylpyrazol-5-one
  • 2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one
  • Edaravone
  • 3-methyl-1-phenyl-2-pyrazolin-5-one
Brand Names
  • Radicava Ors
  • Radicava
IndicationEdaravone is indicated for the treatment of amyotrophic lateral sclerosis (ALS) in the US and Canada.[L41810,L43952] It is also indicated to treat acute ischemic stroke in Japan.[A19140,A19141,L44007]
Categories
  • Antioxidants
  • Central Nervous System Agents
  • Compounds used in a research, industrial, or household setting
  • Free Radical Scavengers
  • Miscellaneous Central Nervous System Agents
ATC-CodeN07XX14
CAS number89-25-8

Drug Targets

NameTarget SequencePharmacological ActionActions
UDP-glucuronosyltransferase 1-1MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...unknownsubstrate
UDP-glucuronosyltransferase 1-6MACLLRSFQRISAGVFFLALWGMVVGDKLLVVPQDGSHWLSMKDIVEVLS...unknownsubstrate
UDP-glucuronosyltransferase 1-7MARAGWTGLLPLYVCLLLTCGFAKAGKLLVVPMDGSHWFTMQSVVEKLIL...unknownsubstrate
UDP-glucuronosyltransferase 1-8MARTGWTSPIPLCVSLLLTCGFAEAGKLLVVPMDGSHWFTMQSVVEKLIL...unknownsubstrate
UDP-glucuronosyltransferase 1-9MACTGWTSPLPLCVCLLLTCGFAEAGKLLVVPMDGSHWFTMRSVVEKLIL...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 4021
ChEMBL CHEMBL290916
ChEBI CHEBI:31530
CCDC/CSD PMPZOL01, PMPZOL04, PMPZOL, OYADUQ, CEHYIB
COD 2219700