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    Also known as: 89-25-8, 3-methyl-1-phenyl-2-pyrazolin-5-one, Radicut, Norphenazone, Mci-186, Developer z
    Molecular Formula
    C10H10N2O
    Molecular Weight
    174.20  g/mol
    InChI Key
    QELUYTUMUWHWMC-UHFFFAOYSA-N
    Edaravone
    An antipyrine derivative that functions as a free radical scavenger and neuroprotective agent. It is used in the treatment of AMYOTROPHIC LATERAL SCLEROSIS and STROKE.
    1 2D Structure

    Edaravone

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-methyl-2-phenyl-4H-pyrazol-3-one
    2.1.2 InChI
    InChI=1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-6H,7H2,1H3
    2.1.3 InChI Key
    QELUYTUMUWHWMC-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=NN(C(=O)C1)C2=CC=CC=C2
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. 1 Phenyl 3 Methyl 5 Pyrazolone

    2. 1-phenyl-3-methyl-5-pyrazolone

    3. 3 Methyl 1 Phenyl 2 Pyrazolin 5 One

    4. 3-methyl-1-phenyl-2-pyrazolin-5-one

    5. Edarabone

    6. Mci 186

    7. Mci-186

    8. Mci186

    9. Norantipyrine

    10. Norphenazone

    11. Phenylmethylpyrazolone

    12. Radicava

    2.2.2 Depositor-Supplied Synonyms

    1. 89-25-8

    2. 3-methyl-1-phenyl-2-pyrazolin-5-one

    3. Radicut

    4. Norphenazone

    5. Mci-186

    6. Developer Z

    7. Methylphenylpyrazolone

    8. Norantipyrine

    9. C.i. Developer 1

    10. Phenyl Methyl Pyrazolone

    11. Phenylmethylpyrazolone

    12. Radicava

    13. 3-methyl-1-phenyl-1h-pyrazol-5(4h)-one

    14. 5-methyl-2-phenyl-2,4-dihydro-3h-pyrazol-3-one

    15. 1-phenyl-3-methyl-5-oxo-2-pyrazoline

    16. 5-methyl-2-phenyl-4h-pyrazol-3-one

    17. 1-phenyl-3-methylpyrazolone

    18. 3h-pyrazol-3-one, 2,4-dihydro-5-methyl-2-phenyl-

    19. 1-phenyl-3-methylpyrazolone-5

    20. 3-methyl-1-phenylpyrazol-5-one

    21. 3-methyl-1-phenyl-2-pyrazoline-5-one

    22. Nci-c03952

    23. 2-pyrazolin-5-one, 3-methyl-1-phenyl-

    24. 5-pyrazolone, 3-methyl-1-phenyl-

    25. 2,4-dihydro-5-methyl-2-phenyl-3h-pyrazol-3-one

    26. Edaravone (mci-186)

    27. 1-fenyl-3-methyl-2-pyrazolin-5-on

    28. 3-methyl-1-phenyl-4,5-dihydro-1h-pyrazol-5-one

    29. Chebi:31530

    30. Nsc-2629

    31. Nsc-26139

    32. Antipyrine Related Compound A

    33. Mls000069602

    34. 3-methyl-1-phenyl-2-pyrazolin-5-one (mci-186)

    35. Ci Developer 1

    36. Ncgc00164015-01

    37. Smr000059020

    38. Dsstox_cid_1130

    39. Dsstox_rid_75961

    40. Dsstox_gsid_21130

    41. Monopyrazolone

    42. Wln: T5nmv Dhj Br& E1

    43. Cas-89-25-8

    44. Ccris 512

    45. Radicut (tn)

    46. Hsdb 4102

    47. 3h-pyrazol-3-one,4-dihydro-5-methyl-2-phenyl-

    48. Sr-01000000135

    49. 1-fenyl-3-methyl-2-pyrazolin-5-on [czech]

    50. Einecs 201-891-0

    51. Mfcd00003138

    52. Unii-s798v6yjrp

    53. Brn 0609575

    54. Ai3-03557

    55. Mci186

    56. (edaravone)

    57. Radicava (tn)

    58. (mci-186)

    59. Cds1_000986

    60. Spectrum_000267

    61. Tocris-0786

    62. Mci-186; Edaravone

    63. Edaravone [usan:inn]

    64. Maybridge1_005738

    65. Opera_id_1057

    66. Spectrum2_001574

    67. Spectrum3_000971

    68. Spectrum4_001091

    69. Spectrum5_001217

    70. M0687

    71. Ec 201-891-0

    72. Schembl4704

    73. Bspbio_001235

    74. Bspbio_002601

    75. Kbiogr_000575

    76. Kbiogr_001502

    77. Kbioss_000575

    78. Kbioss_000747

    79. Ae-641/00371017

    80. Mls001146878

    81. Mls002415675

    82. Mls006011753

    83. Divk1c_001018

    84. Divk1c_002026

    85. Spectrum1503635

    86. Spbio_001508

    87. Chembl290916

    88. Edaravone (usan/jp17/inn)

    89. Dtxsid9021130

    90. Bcbcmap01_000127

    91. Gtpl11994

    92. Hms503k17

    93. Hms557m18

    94. Kbio1_001018

    95. Kbio2_000575

    96. Kbio2_000747

    97. Kbio2_003143

    98. Kbio2_003315

    99. Kbio2_005711

    100. Kbio2_005883

    101. Kbio3_001029

    102. Kbio3_001030

    103. Kbio3_001821

    104. Nsc2629

    105. Ninds_001018

    106. Bcpp000246

    107. Bio1_000438

    108. Bio1_000927

    109. Bio1_001416

    110. Bio2_000448

    111. Bio2_000928

    112. Hms1362m17

    113. Hms1792m17

    114. Hms1990m17

    115. Hms2234m19

    116. Hms3266f04

    117. Hms3403m17

    118. Hms3411l05

    119. Hms3654l15

    120. Hms3675l05

    121. Hms3884a11

    122. Pharmakon1600-01503635

    123. Act07289

    124. Bcp26336

    125. Hy-b0099

    126. Nsc26139

    127. Tox21_112077

    128. Tox21_201747

    129. Tox21_302819

    130. Bdbm50200541

    131. Ccg-39352

    132. Nsc758622

    133. S1326

    134. Stk201315

    135. Zinc18203737

    136. 3-methyl-1-phenyl-2-pyrazolin-5one

    137. Akos000313817

    138. Tox21_112077_1

    139. Ac-4745

    140. Bcp9000635

    141. Cs-1832

    142. Db12243

    143. Nsc-758622

    144. Sb19128

    145. Idi1_001018

    146. Idi1_002203

    147. 1-pehnyl-3-methyl-5-pyrazalone

    148. Ncgc00018218-01

    149. Ncgc00018218-02

    150. Ncgc00018218-03

    151. Ncgc00018218-04

    152. Ncgc00018218-05

    153. Ncgc00018218-06

    154. Ncgc00018218-07

    155. Ncgc00018218-08

    156. Ncgc00018218-10

    157. Ncgc00018218-17

    158. Ncgc00022665-02

    159. Ncgc00022665-04

    160. Ncgc00022665-05

    161. Ncgc00022665-06

    162. Ncgc00256515-01

    163. Ncgc00259296-01

    164. Sbi-0051836.p002

    165. Db-002517

    166. Am20060748

    167. Ft-0608243

    168. Sw148216-2

    169. 5-methyl-2-phenyl-2,4-dihydro-3-pyrazolone

    170. 3-methyl-1-phenyl-2-pyrazoline-5-one, 99%

    171. 4e-901

    172. 5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one

    173. D01552

    174. D86209

    175. 3-?methyl-?1-?phenyl-?2-?pyrazolin-?5-?one

    176. Ab00375776_14

    177. Ab00375776_15

    178. 2 4-dihydro-5-methyl-2-phenyl-3h-pyrazol-3-one

    179. 2,4-dihydro-2-phenyl-5-methyl-3h-pyrazol-3-one

    180. A843105

    181. Q335099

    182. Q-200386

    183. Sr-01000000135-2

    184. Sr-01000000135-3

    185. Sr-01000000135-5

    186. 5-methyl-2-phenyl-2,4-dihydro-3h-pyrazol-3-one #

    187. Brd-k35458079-001-04-2

    188. Brd-k35458079-001-12-5

    189. Brd-k35458079-001-23-2

    190. Z50145861

    191. F0391-0021

    192. 3-methyl-1-phenyl-2-pyrazoline-5-one, Saj Special Grade

    193. 3-methyl-1-phenyl-2-pyrazoline-5-one, Purum, >=98.0% (nt)

    194. 5-methyl-2-phenyl-2,4-dihydro-3h-pyrazol-3-one (edaravone)

    195. Phenazone Impurity A, European Pharmacopoeia (ep) Reference Standard

    196. 5-methyl-2-phenyl-1,2-dihydropyrazol-3-one;3-methyl-1-phenyl-2-pyrazolin-5-one

    197. Antipyrine Related Compound A, United States Pharmacopeia (usp) Reference Standard

    2.3 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 174.20 g/mol
    Molecular Formula C10H10N2O
    XLogP31.3
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count1
    Exact Mass174.079312947 g/mol
    Monoisotopic Mass174.079312947 g/mol
    Topological Polar Surface Area32.7 Ų
    Heavy Atom Count13
    Formal Charge0
    Complexity241
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Indicated for improving neurological symptoms and damage from acute ischemic stroke and delaying disease progression of ALS.

    FDA Label

    Treatment of amyotrophic lateral sclerosis

    Treatment of amyotrophic lateral sclerosis

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Edaravone scavenges free hydroxyl radicals and peroxynitrite radicals which are highly associated with neuronal damage/death from many cerebral vascular disorders such as ischemic strokes and degenerative neurological disorders such as ALS. It exerts a neuroprotective and antioxidant effect and delays disease progression by limiting the extent of lipid peroxidation via free radical generation and cell membrane damage from oxidative stress. It reversed the reduction in regional blood flow and cerebral edema in a case of ischemic stroke.

    5.2 MeSH Pharmacological Classification

    Free Radical Scavengers

    Substances that eliminate free radicals. Among other effects, they protect PANCREATIC ISLETS against damage by CYTOKINES and prevent myocardial and pulmonary REPERFUSION INJURY. (See all compounds classified as Free Radical Scavengers.)

    Neuroprotective Agents

    Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)

    5.3 ATC Code

    N - Nervous system

    N07 - Other nervous system drugs

    N07X - Other nervous system drugs

    N07XX - Other nervous system drugs

    N07XX14 - Edaravone

    5.4 Absorption, Distribution and Excretion

    Absorption

    The peak plasma concentration of the parent drug is reached at the end of infusion, without accumulation of the drug with multiple dosing regimen. The mean Cmax value in healthy male adults is 888ng/mL for intravenous infusion. The values of AUC and Cmax are increased in a dose-proportional relationship. The oral bioavailability in mouse studies is 38% of the I.V. delivery.

    Route of Elimination

    About 0.7-0.9% of the dose is excreted as unchanged drug and 71.0-79.9% of the dose is excreted as metabolites (mostly as glucuronide conjugates) through mainly renal elimination.

    Volume of Distribution

    The mean Vd value following an intravenous infusion of a single 30mg dose is 18.5L/kg.

    Clearance

    The mean total plasma drug clearance following an intravenous infusion of a single 30mg dose is 0.1L/min.

    5.5 Metabolism/Metabolites

    Multiple renal and hepatic uridine diphosphate glucuronosyltransferase (UGT) isoforms catalyze glucuronidation reaction of edaravone to form glucuronide conjugates. Edaravone is also metabolized into sulfate conjugates via sulfotransferase activity, which is the main metabolite form predominantly found circulating in plasma. It is predicted that the sulfate conjugate is hydrolyzed back to edaravone, which is then converted to the glucuronide conjugate in the human kidney before excretion into the urine. These metabolites have no pharmacological activity.

    5.6 Biological Half-Life

    The mean terminal elimination half-life of edaravone is 4.5 to 6 hours and the half-lives of its metabolites are 2 to 2.8 hours.

    5.7 Mechanism of Action

    Nootropic and neuroprotective effects are mediated through inhibiting lipid peroxidation and scavenging free radicals. Edaravone acts to increase prostacyclin production, decrease lipoxygenase metabolism of arachidonic acid by trapping hydroxyl radicals, and inhibit alloxan-induced lipid peroxidation and quench active oxygen species. It targets various kinds of cells, including neurons, endothelial cells and myocardial cells. There is also evidence of reduction of neuronal nitric oxide synthase (nNOS) levels and potentiation of SOD1 levels after transient ischemia in rabbits thus preventing spinal cord injury.

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    05-Feb-2021
    29-Nov-2024
    KGS
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    (USD/KGS)    		 Number of Transactions

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