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Pulse radiolysis study on free radical scavenger edaravone (3-methyl-1-phenyl-2-pyrazolin-5-one). 2007

Mingzhang Lin, and Yosuke Katsumura, and Kuniki Hata, and Yusa Muroya, and Keichi Nakagawa
Advanced Science Research Center, Japan Atomic Energy Agency, 2-4 Shirakata Shirane, Tokaimura, Nakagun, Ibaraki 319-1195, Japan. lin.mingzhang@jaea.go.jp

The reactions between edaravone and various one-electron oxidants such as (*)OH, N(3)(*), Br(2)(-), and SO(4)(-), have been studied by pulse radiolysis techniques. The transient species produced by the reaction of edaravone with (*)OH radical shows an absorption band with lambda(max)=320 nm, while the oxidation by N(3)(*), Br(2)(-), SO(4)(-) and CCl(3)OO(*) results in an absorption band with lambda(max)=345 nm. Different from the previous reports, the main transient species by the reaction of edaravone with (*)OH radical in the absence of O(2) is attributed to OH-adducts. At neutral condition (pH 7), the rate constants of edaravone reacting with (*)OH, N(3)(*), SO(4)(-), CCl(3)OO(*), and e(aq)(-) are estimated to be 8.5x10(9), 5.8x10(9), 6x10(8), 5.0x10(8) and 2.4x10(9)dm(3)mol(-1)s(-1), respectively. From the pH dependence on the formation of electron adducts and on the rate constant of edaravone with hydrated electron, the pK(a) of edaravone is estimated to be 6.9+/-0.1.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D010084 Oxidation-Reduction A chemical reaction in which an electron is transferred from one molecule to another. The electron-donating molecule is the reducing agent or reductant; the electron-accepting molecule is the oxidizing agent or oxidant. Reducing and oxidizing agents function as conjugate reductant-oxidant pairs or redox pairs (Lehninger, Principles of Biochemistry, 1982, p471). Redox,Oxidation Reduction
D011675 Pulse Radiolysis Use of a pulse of X-rays or fast electrons to generate free radicals for spectroscopic examination. Radiolysis, Pulse
D005609 Free Radicals Highly reactive molecules with an unsatisfied electron valence pair. Free radicals are produced in both normal and pathological processes. Free radicals include reactive oxygen and nitrogen species (RONS). They are proven or suspected agents of tissue damage in a wide variety of circumstances including radiation, damage from environment chemicals, and aging. Natural and pharmacological prevention of free radical damage is being actively investigated. Free Radical
D006863 Hydrogen-Ion Concentration The normality of a solution with respect to HYDROGEN ions; H+. It is related to acidity measurements in most cases by pH pH,Concentration, Hydrogen-Ion,Concentrations, Hydrogen-Ion,Hydrogen Ion Concentration,Hydrogen-Ion Concentrations
D000042 Absorption The physical or physiological processes by which substances, tissue, cells, etc. take up or take in other substances or energy.
D000077553 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-Phenyl-3-methyl-5-pyrazolone,3-Methyl-1-phenyl-2-pyrazolin-5-one,Edarabone,MCI 186,MCI-186,Norantipyrine,Norphenazone,Phenylmethylpyrazolone,Radicava,1 Phenyl 3 methyl 5 pyrazolone,3 Methyl 1 phenyl 2 pyrazolin 5 one,MCI186
D000983 Antipyrine An analgesic and antipyretic that has been given by mouth and as ear drops. Antipyrine is often used in testing the effects of other drugs or diseases on drug-metabolizing enzymes in the liver. (From Martindale, The Extra Pharmacopoeia, 30th ed, p29) Phenazone,Anodynin,Pyramidone
D016166 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. Free Radical Scavenger,Radical Scavenger, Free,Scavenger, Free Radical,Scavengers, Free Radical

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