edaravone   Click here for help

GtoPdb Ligand ID: 11994

Synonyms: MCI-186 | MCI186 | Radicava® | Radicut®
PDB Ligand
Compound class: Synthetic organic
Comment: Edaravone (MCI-186) is a free radical scavenger [1]. It is used clinically for its neuroprotective action.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 1
Topological polar surface area 32.67
Molecular weight 174.08
XLogP 1.49
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES O=C1CC(=NN1c1ccccc1)C
Isomeric SMILES CC1=NN(C(=O)C1)c1ccccc1
InChI InChI=1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-6H,7H2,1H3
InChI Key QELUYTUMUWHWMC-UHFFFAOYSA-N
References
1. Abe S, Kirima K, Tsuchiya K, Okamoto M, Hasegawa T, Houchi H, Yoshizumi M, Tamaki T. (2004)
The reaction rate of edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one (MCI-186)) with hydroxyl radical.
Chem Pharm Bull (Tokyo), 52 (2): 186-91. [PMID:14758002]
2. Jackson C, Heiman-Patterson T, Kittrell P, Baranovsky T, McAnanama G, Bower L, Agnese W, Martin M. (2019)
Radicava (edaravone) for amyotrophic lateral sclerosis: US experience at 1 year after launch.
Amyotroph Lateral Scler Frontotemporal Degener, 20 (7-8): 605-610. [PMID:31364409]
3. Kaste M, Murayama S, Ford GA, Dippel DW, Walters MR, Tatlisumak T, MCI-186 study group. (2013)
Safety, tolerability and pharmacokinetics of MCI-186 in patients with acute ischemic stroke: new formulation and dosing regimen.
Cerebrovasc Dis, 36 (3): 196-204. [PMID:24135530]
4. Lapchak PA. (2010)
A critical assessment of edaravone acute ischemic stroke efficacy trials: is edaravone an effective neuroprotective therapy?.
Expert Opin Pharmacother, 11 (10): 1753-63. [PMID:20491547]
5. Shan H, Jiao G, Cheng X, Dou Z. (2021)
Safety and efficacy of edaravone for patients with acute stroke: A protocol for randomized clinical trial.
Medicine (Baltimore), 100 (8): e24811. [PMID:33663100]
6. Yoshino H. (2019)
Edaravone for the treatment of amyotrophic lateral sclerosis.
Expert Rev Neurother, 19 (3): 185-193. [PMID:30810406]