Edaravone

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Edaravone are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Edaravone?

The molecule Edaravone presents a molecular formula of C10H10N2O and its IUPAC name is 5-methyl-2-phenyl-4H-pyrazol-3-one.

Edaravone (INN, trade name MCI-186) is a free radical scavenger that is used as a neuroprotective agent. It is the active metabolite of idebenone and is structurally similar to CoQ10..

Edaravone was first synthesized in 1977 and later developed as a treatment for cerebral ischemia in Japan. It is approved for use in Japan and South Korea for the treatment of cerebral infarction, and has been used off-label for amyotrophic lateral sclerosis (ALS) in the United States..

Edaravone is thought to work by scavenging free radicals and reducing oxidative stress. It has also been shown to inhibit the production of nitric oxide and tumor necrosis factor-alpha, and to upregulate antioxidant enzymes..

A phase III clinical trial in Japan showed that edaravone was effective in reducing the rate of decline in ALS patients. However, a phase III clinical trial in the United States did not show a significant benefit of edaravone in ALS patients..

Edaravone is generally well-tolerated, with the most common side effects being headache, dizziness, and rash..

Edaravone is a promising treatment for ALS, but further research is needed to confirm its efficacy..

3D structure

Cartesian coordinates

Geometry of Edaravone in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Edaravone QELUYTUMUWHWMC-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Edaravone

 

Molecule descriptors

 
IUPAC name5-methyl-2-phenyl-4H-pyrazol-3-one
InChI codeInChI=1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-6H,7H2,1H3
InChI KeyQELUYTUMUWHWMC-UHFFFAOYSA-N
SMILESCC1=NN(c2ccccc2)C(=O)C1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (Edaravone)
  • (MCI-186)
  • 1-Fenyl-3-methyl-2-pyrazolin-5-on
  • 1-PEHNYL-3-METHYL-5-PYRAZALONE
  • 1-Phenyl-3-methyl-5-oxo-2-pyrazoline
  • 1-Phenyl-3-methylpyrazolone
  • 1-Phenyl-3-methylpyrazolone-5
  • 2 4-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one
  • 2,4-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one
  • 2,4-dihydro-2-phenyl-5-methyl-3H-pyrazol-3-one
  • 2-Pyrazolin-5-one, 3-methyl-1-phenyl-
  • 3-?Methyl-?1-?phenyl-?2-?pyrazolin-?5-?one
  • 3-METHYL-1-PHENYL-2-PYRAZOLIN-5-ONE
  • 3-METHYL-1-PHENYL-2-PYRAZOLIN-5-ONE (MCI-186)
  • 3-Methyl-1-phenyl-1H-pyrazol-5(4H)-one
  • 3-Methyl-1-phenyl-2-pyrazoline-5-one
  • 3-Methyl-1-phenylpyrazol-5-one
  • 3-methyl-1-phenyl-2-pyrazolin-5one
  • 3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one
  • 3H-Pyrazol-3-one, 2,4-dihydro-5-methyl-2-phenyl-
  • 3H-Pyrazol-3-one,4-dihydro-5-methyl-2-phenyl-
  • 4E-901
  • 5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one;3-Methyl-1-phenyl-2-pyrazolin-5-one
  • 5-Methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
  • 5-Methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one #
  • 5-Methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one (Edaravone)
  • 5-Pyrazolone, 3-methyl-1-phenyl-
  • 5-methyl-2-phenyl-2,4-dihydro-3-pyrazolone
  • 5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one
  • 5-methyl-2-phenyl-2,4-dihydropyrazol-3-one
  • 5-methyl-2-phenyl-4H-pyrazol-3-one
  • 89-25-8
  • A843105
  • AB00375776_14
  • AB00375776_15
  • AC-4745
  • ACT07289
  • AE-641/00371017
  • AI3-03557
  • AM20060748
  • Antipyrine related compound a
  • BCBcMAP01_000127
  • BCP26336
  • BCP9000635
  • BCPP000246
  • BDBM50200541
  • BRN 0609575
  • BSPBio_001235
  • BSPBio_002601
  • Bio1_000438
  • Bio1_000927
  • Bio1_001416
  • Bio2_000448
  • Bio2_000928
  • C.I. Developer 1
  • CCG-39352
  • CCRIS 512
  • CDS1_000986
  • CI Developer 1
  • CS-1832
  • D01552
  • D86209
  • DB-002517
  • DB12243
  • DSSTox_CID_1130
  • DSSTox_GSID_21130
  • DSSTox_RID_75961
  • Developer Z
  • DivK1c_001018
  • DivK1c_002026
  • EC 201-891-0
  • Edaravone
  • Edaravone (MCI-186)
  • Edaravone (USAN/JP17/INN)
  • F0391-0021
  • FT-0608243
  • GTPL11994
  • HMS1362M17
  • HMS1792M17
  • HMS1990M17
  • HMS2234M19
  • HMS3266F04
  • HMS3403M17
  • HMS3411L05
  • HMS3654L15
  • HMS3675L05
  • HMS3884A11
  • HMS503K17
  • HMS557M18
  • HSDB 4102
  • HY-B0099
  • IDI1_001018
  • IDI1_002203
  • KBio1_001018
  • KBio2_000575
  • KBio2_000747
  • KBio2_003143
  • KBio2_003315
  • KBio2_005711
  • KBio2_005883
  • KBio3_001029
  • KBio3_001030
  • KBio3_001821
  • KBioGR_000575
  • KBioGR_001502
  • KBioSS_000575
  • KBioSS_000747
  • M0687
  • MCI-186
  • MCI-186; Edaravone
  • MCI186
  • MFCD00003138
  • MLS000069602
  • MLS001146878
  • MLS002415675
  • MLS006011753
  • Maybridge1_005738
  • Methylphenylpyrazolone
  • Monopyrazolone
  • NCGC00018218-01
  • NCGC00018218-02
  • NCGC00018218-03
  • NCGC00018218-04
  • NCGC00018218-05
  • NCGC00018218-06
  • NCGC00018218-07
  • NCGC00018218-08
  • NCGC00018218-10
  • NCGC00018218-17
  • NCGC00022665-02
  • NCGC00022665-04
  • NCGC00022665-05
  • NCGC00022665-06
  • NCGC00164015-01
  • NCGC00256515-01
  • NCGC00259296-01
  • NCI-C03952
  • NINDS_001018
  • NSC-26139
  • NSC-2629
  • NSC-758622
  • NSC26139
  • NSC2629
  • NSC758622
  • Norantipyrine
  • Norphenazone
  • Opera_ID_1057
  • Pharmakon1600-01503635
  • Phenyl methyl pyrazolone
  • Phenylmethylpyrazolone
  • Q-200386
  • Q335099
  • Radicava
  • Radicut
  • SB19128
  • SBI-0051836.P002
  • SMR000059020
  • SPECTRUM1503635
  • SR-01000000135
  • SR-01000000135-2
  • SR-01000000135-3
  • SR-01000000135-5
  • STK201315
  • SW148216-2
  • Tocris-0786
  • WLN: T5NMV DHJ BR& E1
  • Z50145861
  • edaravone
  • s1326

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC18203737
  • CAS-89-25-8
  • UNII-S798V6YJRP
  • AKOS000313817
  • BRD-K35458079-001-04-2
  • BRD-K35458079-001-12-5
  • BRD-K35458079-001-23-2
  • DTXSID9021130
  • CHEMBL290916
  • CHEBI:31530
  • Tox21_112077
  • Tox21_201747
  • Tox21_302819
  • Tox21_112077_1
  • EINECS 201-891-0
  • SPBio_001508
  • SCHEMBL4704
  • Spectrum_000267
  • Spectrum2_001574
  • Spectrum3_000971
  • Spectrum4_001091
  • Spectrum5_001217

Physico-Chemical properties

IUPAC name5-methyl-2-phenyl-4H-pyrazol-3-one
Molecular formulaC10H10N2O
Molecular weight174.199
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity58.30
LogP1.3
Topological polar surface area32.7

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.