EDARAVONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H10N2O
Molecular Weight	174.1992
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NN(C(O)=C1)C2=CC=CC=C2

InChI

InChIKey=PLVBQEFRONZLHO-UHFFFAOYSA-N

InChI=1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-7,13H,1H3

HIDE SMILES / InChI

Description

Edaravone is a free radical scavenger developed for the treatment of amyotrophic lateral sclerosis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
CHEMBL1689064: Hydroxyl Radical 1	Binding Agent 942	Stroke

Conditions

Condition	Modality	Targets	Highest Phase	Product
Amyotrophic Lateral Sclerosis 37	Primary	CHEMBL1689064: Hydroxyl Radical	Approved 7777	RADICUT
Stroke 152	Primary	CHEMBL1689064: Hydroxyl Radical	Approved 7777	RADICUT

PubMed

Title	Date	PubMed
Protection by a radical scavenger edaravone against cisplatin-induced nephrotoxicity in rats.	2002 Sep 13	12231392
Normalization by edaravone, a free radical scavenger, of irradiation-reduced endothelial nitric oxide synthase expression.	2003 Aug 22	12969758
Edaravone protects against lung injury induced by intestinal ischemia/reperfusion in rat.	2005 Feb 1	15629865
MCI-186 (edaravone), a free radical scavenger, attenuates hepatic warm ischemia-reperfusion injury in rats.	2005 Jul	15948865
Edaravone, a novel radical scavenger, inhibits oxidative modification of low-density lipoprotein (LDL) and reverses oxidized LDL-mediated reduction in the expression of endothelial nitric oxide synthase.	2005 Mar	15721014
The antioxidant edaravone attenuates pressure overload-induced left ventricular hypertrophy.	2005 May	15824197
Effect of a novel free radical scavenger, edaravone, on puromycin aminonucleoside induced nephrosis in rats.	2005 Oct	16079985
A free radical scavenger but not FGF-2-mediated angiogenic therapy rescues myonephropathic metabolic syndrome in severe hindlimb ischemia.	2006 Apr	16301206
Protective effect of the radical scavenger edaravone against methamphetamine-induced dopaminergic neurotoxicity in mouse striatum.	2006 Aug 7	16784740
Edaravone inhibits rheumatoid synovial cell proliferation and migration.	2006 Feb	16390820
Electron spin resonance and spin trapping technique provide direct evidence that edaravone prevents acute ischemia-reperfusion injury of the liver by limiting free radical-mediated tissue damage.	2006 Jun	16753835
An antioxidant treatment potentially protects myocardial energy metabolism by regulating uncoupling protein 2 expression in a chronic beta-adrenergic stimulation rat model.	2006 May 15	16580698
Edaravone reduces ischemia-reperfusion injury mediators in rat liver.	2007 Jan	17064733
A case report of acute renal failure and fulminant hepatitis associated with edaravone administration in a cerebral infarction patient.	2007 Jun	17498008
[Ischemic stroke associated with LH-RH analogue (leuprorelin) administration in a young woman].	2007 May	17585607
Administration of free radical scavenger edaravone associated with higher frequency of hemorrhagic transformation in patients with cardiogenic embolism.	2008 Jul	18654047
Edaravone protects against MPP+ -induced cytotoxicity in rat primary cultured astrocytes via inhibition of mitochondrial apoptotic pathway.	2008 Sep	18643790
[Effects of edaravone on the expression of interleukin-1beta, nuclear factor-kappaB and neuron apoptosis in juvenile rat hippocampus after status convulsion].	2009 Aug	19951488
Edaravone, a free radical scavenger, inhibits MMP-9-related brain hemorrhage in rats treated with tissue plasminogen activator.	2009 Feb	19095969
Expression of syndecan-2 in the amoeboid microglial cells and its involvement in inflammation in the hypoxic developing brain.	2009 Feb	18803305
Expression of angiotensin II and its receptors in the normal and hypoxic amoeboid microglial cells and murine BV-2 cells.	2009 Feb 18	19118600
Neuroprotective effects of edaravone, a free radical scavenger, on the rat hippocampus after pilocarpine-induced status epilepticus.	2009 Jan	18672383
Reactive oxygen species modulate growth of cerebral aneurysms: a study using the free radical scavenger edaravone and p47phox(-/-) mice.	2009 Jul	19381132
Oxygen-glucose deprivation activates 5-lipoxygenase mediated by oxidative stress through the p38 mitogen-activated protein kinase pathway in PC12 cells.	2009 Mar	18951527
Acute urinary retention and subsequent catheterization cause lipid peroxidation and oxidative DNA damage in the bladder: preventive effect of edaravone, a free-radical scavenger.	2009 Sep	19338546
Protective effect of edaravone against PrP106-126-induced PC12 cell death.	2010 Jul-Aug	20806394
Edaravone improves the expression of nerve growth factor in human astrocytes subjected to hypoxia/reoxygenation.	2010 Mar	19954754
Protective effect of edaravone, a free-radical scavenger, on ischaemia-reperfusion injury in the rat testis.	2010 Mar	19694712
Protective effects of the free radical scavenger edaravone on acute pancreatitis-associated lung injury.	2010 Mar 25	20035747
[Effects of edaravone on the expression of GRP78, Caspase-12, and neuron apoptosis in juvenile rat hippocampus after status convulsive].	2011 Jan	21429313
Edaravone inhibits hypoxia-induced trophoblast-soluble Fms-like tyrosine kinase 1 expression: a possible therapeutic approach to preeclampsia.	2014 Jul	24840734
Effects of Astragaloside IV combined with the active components of Panax notoginseng on oxidative stress injury and nuclear factor-erythroid 2-related factor 2/heme oxygenase-1 signaling pathway after cerebral ischemia-reperfusion in mice.	2014 Oct	25422538
A novel pyrazolone-based derivative induces apoptosis in human esophageal cells via reactive oxygen species (ROS) generation and caspase-dependent mitochondria-mediated pathway.	2015 Apr 25	25684395
Change in soluble epoxide hydrolase (sEH) during cisplatin-induced acute renal failure in mice.	2015 Aug	26165641
Ginsenoside Rd attenuates Aβ25-35-induced oxidative stress and apoptosis in primary cultured hippocampal neurons.	2015 Sep 5	26111763

Patents

Sample Use Guides

In Vivo Use Guide

30 mg of edaravone diluted with an appropriate volume of physiological saline, intravenously over 30 minutes twice a day in the morning and the evening (stroke); 60 mg of edaravone diluted with an appropriate volume of physiological saline, intravenously over 60 minutes once a day (amyotrophic lateral sclerosis).

Route of Administration: Intravenous

In Vitro Use Guide

1 uM or more of edaravone inhibited cultured vascular endothelial cell injury in vitro caused by 15-HPETE (hydroperoxyeicosatetraenoic acid).

Name

Type

Language

EDARAVONE

Official Name

English

3H-PYRAZOL-3-ONE, 2,4-DIHYDRO-5-METHYL-2-PHENYL-

Systematic Name

English

COLOREX PMP

Brand Name

English

ANTIPYRINE RELATED COMPOUND A

Common Name

English

NORPHENAZONE [MI]

Common Name

English

NSC-12

Code

English

NSC-2629

Code

English

C.I. DEVELOPER 1

Common Name

English

NORPHENAZONE

Common Name

English

DEVELOPER Z

Common Name

English

RADICUT

Brand Name

English

EDARAVONE [USAN]

Common Name

English

EDARAVONE [HSDB]

Common Name

English

EDARAVONE [WHO-DD]

Common Name

English

MCI-186

Code

English

1-PHENYL-3-METHYL-5-PYRAZOLONE

Systematic Name

English

RADICAVA

Brand Name

English

NSC-26139

Code

English

JAROCOL PMP

Brand Name

English

3-METHYL-1-PHENYL-2-PYRAZOLIN-5-ONE

Systematic Name

English

PHENYL METHYL PYRAZOLONE

Official Name

English

ANTIPYRINE RELATED COMPOUND A [USP-RS]

Common Name

English

EDARAVONE [MART.]

Common Name

English

EDARAVONE [JAN]

Common Name

English

PHENYLMETHYLPYRAZOLONE

Systematic Name

English

PHENYL METHYL PYRAZOLONE [INCI]

Common Name

English

EDARAVONE [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1509