U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H10N2O
Molecular Weight 174.1996
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EDARAVONE

SMILES

Cc1cc(n(-c2ccccc2)n1)O

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

CNS Activity

Curator's Comment:: Edaravone crossed BBB in rats.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL1689064: Hydroxyl Radical
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
RADICUT

Approved Use

Improvement of neurological symptoms, disorder of activities of daily living, and functional disorder associated with acute ischaemic stroke; Inhibition on progression of functional disorder in patients with amyotrophic lateral sclerosis (ALS).

Launch Date

1.26342726E12
Primary
RADICUT

Approved Use

Improvement of neurological symptoms, disorder of activities of daily living, and functional disorder associated with acute ischaemic stroke; Inhibition on progression of functional disorder in patients with amyotrophic lateral sclerosis (ALS).

Launch Date

1.26342726E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.48 μg/mL
30 mg 2 times / day multiple, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
EDARAVONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2030.2 ng/mL
30 mg single, sublingual
dose: 30 mg
route of administration: Sublingual
experiment type: SINGLE
co-administered:
EDARAVONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2354 ng/mL
30 mg single, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EDARAVONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1049.3 ng/mL
60 mg 1 times / day multiple, intravenous
dose: 60 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
EDARAVONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
5.24 mg × h/L
30 mg 2 times / day multiple, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
EDARAVONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5576.72 ng × h/mL
30 mg single, sublingual
dose: 30 mg
route of administration: Sublingual
experiment type: SINGLE
co-administered:
EDARAVONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
5981.91 ng × h/mL
30 mg single, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EDARAVONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1373.5 ng × h/mL
60 mg 1 times / day multiple, intravenous
dose: 60 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
EDARAVONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.52 h
30 mg 2 times / day multiple, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
EDARAVONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2.83 h
30 mg single, sublingual
dose: 30 mg
route of administration: Sublingual
experiment type: SINGLE
co-administered:
EDARAVONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
3.04 h
30 mg single, intravenous
dose: 30 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EDARAVONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
0.86 h
60 mg 1 times / day multiple, intravenous
dose: 60 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
EDARAVONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
60 mg 1 times / day multiple, intravenous
Recommended
Dose: 60 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 60 mg, 1 times / day
Sources: Page: p. 77
unhealthy, 58.8 years (range: 29 - 75 years)
n = 184
Health Status: unhealthy
Age Group: 58.8 years (range: 29 - 75 years)
Sex: M+F
Population Size: 184
Sources: Page: p. 77
Disc. AE: Respiratory disorder, Respiratory failure...
AEs leading to
discontinuation/dose reduction:
Respiratory disorder (0.5%)
Respiratory failure (1.1%)
Toxic skin eruption (0.5%)
Sources: Page: p. 77
AEs

AEs

AESignificanceDosePopulation
Respiratory disorder 0.5%
Disc. AE
60 mg 1 times / day multiple, intravenous
Recommended
Dose: 60 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 60 mg, 1 times / day
Sources: Page: p. 77
unhealthy, 58.8 years (range: 29 - 75 years)
n = 184
Health Status: unhealthy
Age Group: 58.8 years (range: 29 - 75 years)
Sex: M+F
Population Size: 184
Sources: Page: p. 77
Toxic skin eruption 0.5%
Disc. AE
60 mg 1 times / day multiple, intravenous
Recommended
Dose: 60 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 60 mg, 1 times / day
Sources: Page: p. 77
unhealthy, 58.8 years (range: 29 - 75 years)
n = 184
Health Status: unhealthy
Age Group: 58.8 years (range: 29 - 75 years)
Sex: M+F
Population Size: 184
Sources: Page: p. 77
Respiratory failure 1.1%
Disc. AE
60 mg 1 times / day multiple, intravenous
Recommended
Dose: 60 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 60 mg, 1 times / day
Sources: Page: p. 77
unhealthy, 58.8 years (range: 29 - 75 years)
n = 184
Health Status: unhealthy
Age Group: 58.8 years (range: 29 - 75 years)
Sex: M+F
Population Size: 184
Sources: Page: p. 77
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes [IC50 121 uM]
yes [IC50 13.6 uM]
yes [IC50 2.74 uM]
yes [IC50 72.3 uM]
yes [IC50 84.5 uM]
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Protection by a radical scavenger edaravone against cisplatin-induced nephrotoxicity in rats.
2002 Sep 13
A free radical scavenger, edaravone, attenuates steatosis and cell death via reducing inflammatory cytokine production in rat acute liver injury.
2003 Aug
Normalization by edaravone, a free radical scavenger, of irradiation-reduced endothelial nitric oxide synthase expression.
2003 Aug 22
Protective effect of edaravone against streptomycin-induced vestibulotoxicity in the guinea pig.
2003 Mar 7
Edaravone, a novel free radical scavenger, prevents liver injury and mortality in rats administered endotoxin.
2003 Oct
Edaravone, a newly developed radical scavenger, protects against ischemia-reperfusion injury of the small intestine in rats.
2004 Jan
Radical scavenger edaravone developed for clinical use ameliorates ischemia/reperfusion injury in rat kidney.
2004 May
Edaravone protects against lung injury induced by intestinal ischemia/reperfusion in rat.
2005 Feb 1
Free radical scavenger (edaravone) prevents endotoxin-induced liver injury after partial hepatectomy in rats.
2005 Jan
MCI-186 (edaravone), a free radical scavenger, attenuates hepatic warm ischemia-reperfusion injury in rats.
2005 Jul
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
The antioxidant edaravone attenuates pressure overload-induced left ventricular hypertrophy.
2005 May
Clinical analysis of 207 patients who developed renal disorders during or after treatment with edaravone reported during post-marketing surveillance.
2007 Dec
Edaravone reduces ischemia-reperfusion injury mediators in rat liver.
2007 Jan
Edaravone inhibits the induction of iNOS gene expression at transcriptional and posttranscriptional steps in murine macrophages.
2008 Dec
Administration of free radical scavenger edaravone associated with higher frequency of hemorrhagic transformation in patients with cardiogenic embolism.
2008 Jul
The radical scavenger edaravone counteracts diabetes in multiple low-dose streptozotocin-treated mice.
2008 Mar 31
Edaravone protects against MPP+ -induced cytotoxicity in rat primary cultured astrocytes via inhibition of mitochondrial apoptotic pathway.
2008 Sep
[Effects of edaravone on the expression of interleukin-1beta, nuclear factor-kappaB and neuron apoptosis in juvenile rat hippocampus after status convulsion].
2009 Aug
Edaravone, a free radical scavenger, inhibits MMP-9-related brain hemorrhage in rats treated with tissue plasminogen activator.
2009 Feb
Expression of syndecan-2 in the amoeboid microglial cells and its involvement in inflammation in the hypoxic developing brain.
2009 Feb
Neuroprotective effects of edaravone, a free radical scavenger, on the rat hippocampus after pilocarpine-induced status epilepticus.
2009 Jan
Protective effect of edaravone against tobramycin-induced ototoxicity.
2009 Jan
Protective effect of edaravone against PrP106-126-induced PC12 cell death.
2010 Jul-Aug
Edaravone improves the expression of nerve growth factor in human astrocytes subjected to hypoxia/reoxygenation.
2010 Mar
Protective effect of edaravone, a free-radical scavenger, on ischaemia-reperfusion injury in the rat testis.
2010 Mar
Protective effects of the free radical scavenger edaravone on acute pancreatitis-associated lung injury.
2010 Mar 25
[Effects of edaravone on the expression of GRP78, Caspase-12, and neuron apoptosis in juvenile rat hippocampus after status convulsive].
2011 Jan
Edaravone, a novel antidote against lung injury and pulmonary fibrosis induced by paraquat?
2011 Jan
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
Change in soluble epoxide hydrolase (sEH) during cisplatin-induced acute renal failure in mice.
2015 Aug
Patents

Sample Use Guides

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
HSDB   INN   JAN   MART.   USAN   WHO-DD  
USAN   INN  
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
USP-RS  
Common Name English
NORPHENAZONE [MI]
Common Name English
NSC-12
Code English
NSC-2629
Code English
C.I. DEVELOPER 1
Common Name English
NORPHENAZONE
MI  
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
EDARAVONE [ORANGE BOOK]
Common 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
INCI  
INCI  
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
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
WHO-ATC N07XX14
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
FDA ORPHAN DRUG 478215
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
FDA ORPHAN DRUG 754420
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
EU-Orphan Drug EU/3/15/1510
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
FDA ORPHAN DRUG 465514
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
Code System Code Type Description
JAPANESE REVIEW
RADICUT
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY APPROVED JUNE 2015
DRUG BANK
DB12243
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
RXCUI
1921877
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
CAS
89-25-8
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
MESH
C005435
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
ChEMBL
CHEMBL290916
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
USP_CATALOG
1040016
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY USP-RS
PUBCHEM
4021
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
CAS
942-32-5
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
ALTERNATIVE
HSDB
4102
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
WIKIPEDIA
EDARAVONE
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-891-0
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
CAS
19735-89-8
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
ALTERNATIVE
INN
7362
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
DRUG CENTRAL
4156
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
EVMPD
SUB06453MIG
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
MERCK INDEX
M8072
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
213-390-4
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
ALTERNATIVE
NCI_THESAURUS
C74323
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
EPA CompTox
942-32-5
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY
FDA UNII
S798V6YJRP
Created by admin on Sat Jun 26 05:08:30 UTC 2021 , Edited by admin on Sat Jun 26 05:08:30 UTC 2021
PRIMARY