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Chemical Compound Review

Radicut     5-methyl-2-phenyl-4H-pyrazol- 3-one

Synonyms: edaravone, Norphenazone, Norantipyrine, Monopyrazolone, Calyculin-A, ...
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Disease relevance of Phenyl methyl pyrazolone


Psychiatry related information on Phenyl methyl pyrazolone


High impact information on Phenyl methyl pyrazolone

  • The antioxidant edaravone decreased oxidative stress in damaged brains, more pronounced in the Hq mice, and further reduced brain injury in Hq but not in Wt mice [6].
  • Edaravone treatment decreased the neutrophil infiltration, the lipid membrane peroxidation, and the expression of proinflammatory cytokine interleukin-6 mRNA in the lungs after intestinal I/R compared to the I/R-treated rat lungs without edaravone treatment [1].
  • Inhibition of brain damage by edaravone, a free radical scavenger, can be monitored by plasma biomarkers that detect oxidative and astrocyte damage in patients with acute cerebral infarction [7].
  • Edaravone was administered to 27 randomly selected patients (GIa, n = 13; GIIa, n = 14) and its efficacy was studied by comparing their plasma OxLDL, S-100B, and MnSOD levels to those in patients without edaravone (GIb, n = 11, GIIb, n = 13) [7].
  • The CYP2C subfamily contains the predominant enzymes for norantipyrine formation, and CYP1A2 is also involved [8].

Chemical compound and disease context of Phenyl methyl pyrazolone


Biological context of Phenyl methyl pyrazolone


Anatomical context of Phenyl methyl pyrazolone

  • MCI-186 seems to have protective effects against hepatic warm I/R injury by attenuating the damage of the hepatocyte, which is the major target of oxidative damage in this model [18].
  • METHODS: Ischemic acute renal failure was induced by 45-minute clamp of the left renal artery followed by administration of edaravone [14].
  • We investigated the in vitro effects of edaravone on copper- and endothelial cell-mediated LDL oxidation, and the expression of eNOS in human umbilical vein endothelial cells (HUVEC) modulated by oxidized LDL [19].
  • Edaravone significantly suppressed the production of NO and ROS by activated microglia, though it did not suppress production of inflammatory cytokines [16].
  • In the remaining four lambs, 60 mg of MCI-186 was administered into the maternal circulation from shortly before the end of 10-min persistent total umbilical cord occlusion [20].

Associations of Phenyl methyl pyrazolone with other chemical compounds


Gene context of Phenyl methyl pyrazolone


Analytical, diagnostic and therapeutic context of Phenyl methyl pyrazolone


  1. Edaravone protects against lung injury induced by intestinal ischemia/reperfusion in rat. Ito, K., Ozasa, H., Horikawa, S. Free Radic. Biol. Med. (2005) [Pubmed]
  2. Effect of MCI-186 on brain edema in rats. Nishi, H., Watanabe, T., Sakurai, H., Yuki, S., Ishibashi, A. Stroke (1989) [Pubmed]
  3. Involvement of free radicals in cerebral vascular reperfusion injury evaluated in a transient focal cerebral ischemia model of rat. Nakashima, M., Niwa, M., Iwai, T., Uematsu, T. Free Radic. Biol. Med. (1999) [Pubmed]
  4. Does edaravone (MCI- 186) act as an antioxidant and a neuroprotector in experimental traumatic brain injury? Dohi, K., Satoh, K., Nakamachi, T., Yofu, S., Hiratsuka, K., Nakamura, S., Ohtaki, H., Yoshikawa, T., Shioda, S., Aruga, T. Antioxid. Redox Signal. (2007) [Pubmed]
  5. Influence of short-term water deprivation on antipyrine disposition in calves. Janus, K., Muszczynski, Z., Suszycka, J. Res. Vet. Sci. (1997) [Pubmed]
  6. Apoptosis-inducing factor is a major contributor to neuronal loss induced by neonatal cerebral hypoxia-ischemia. Zhu, C., Wang, X., Huang, Z., Qiu, L., Xu, F., Vahsen, N., Nilsson, M., Eriksson, P.S., Hagberg, H., Culmsee, C., Plesnila, N., Kroemer, G., Blomgren, K. Cell Death Differ. (2007) [Pubmed]
  7. Inhibition of brain damage by edaravone, a free radical scavenger, can be monitored by plasma biomarkers that detect oxidative and astrocyte damage in patients with acute cerebral infarction. Uno, M., Kitazato, K.T., Suzue, A., Matsuzaki, K., Harada, M., Itabe, H., Nagahiro, S. Free Radic. Biol. Med. (2005) [Pubmed]
  8. Antipyrine as a probe for human oxidative drug metabolism: identification of the cytochrome P450 enzymes catalyzing 4-hydroxyantipyrine, 3-hydroxymethylantipyrine, and norantipyrine formation. Engel, G., Hofmann, U., Heidemann, H., Cosme, J., Eichelbaum, M. Clin. Pharmacol. Ther. (1996) [Pubmed]
  9. Hepatic drug clearance in patients with mild cystic fibrosis. Kearns, G.L., Crom, W.R., Karlson, K.H., Mallory, G.B., Evans, W.E. Clin. Pharmacol. Ther. (1996) [Pubmed]
  10. Protective effect of edaravone against hypoxia-reoxygenation injury in rabbit cardiomyocytes. Yamawaki, M., Sasaki, N., Shimoyama, M., Miake, J., Ogino, K., Igawa, O., Tajima, F., Shigemasa, C., Hisatome, I. Br. J. Pharmacol. (2004) [Pubmed]
  11. Protective effects of MCI-186 on cerebral ischemia: possible involvement of free radical scavenging and antioxidant actions. Watanabe, T., Yuki, S., Egawa, M., Nishi, H. J. Pharmacol. Exp. Ther. (1994) [Pubmed]
  12. Antipyrine clearance and metabolite formation in patients with alcoholic cirrhosis. Teunissen, M.W., Spoelstra, P., Koch, C.W., Weeda, B., van Duyn, W., Janssens, A.R., Breimer, D.D. British journal of clinical pharmacology. (1984) [Pubmed]
  13. Edaravone inhibits acute renal injury and cyst formation in cisplatin-treated rat kidney. Iguchi, T., Nishikawa, M., Chang, B., Muroya, O., Sato, E.F., Nakatani, T., Inoue, M. Free Radic. Res. (2004) [Pubmed]
  14. Radical scavenger edaravone developed for clinical use ameliorates ischemia/reperfusion injury in rat kidney. Doi, K., Suzuki, Y., Nakao, A., Fujita, T., Noiri, E. Kidney Int. (2004) [Pubmed]
  15. Potent free radical scavenger, edaravone, suppresses oxidative stress-induced endothelial damage and early atherosclerosis. Xi, H., Akishita, M., Nagai, K., Yu, W., Hasegawa, H., Eto, M., Kozaki, K., Toba, K. Atherosclerosis (2007) [Pubmed]
  16. The radical scavenger edaravone prevents oxidative neurotoxicity induced by peroxynitrite and activated microglia. Banno, M., Mizuno, T., Kato, H., Zhang, G., Kawanokuchi, J., Wang, J., Kuno, R., Jin, S., Takeuchi, H., Suzumura, A. Neuropharmacology (2005) [Pubmed]
  17. A free radical scavenger, edaravone (MCI-186), diminishes intestinal neutrophil lipid peroxidation and bacterial translocation in a rat hemorrhagic shock model. Mori, T., Yamamoto, H., Tabata, T., Shimizu, T., Endo, Y., Hanasawa, K., Fujimiya, M., Tani, T. Crit. Care Med. (2005) [Pubmed]
  18. Beneficial effect of MCI-186 on hepatic warm ischemia-reperfusion in the rat. Ninomiya, M., Shimada, M., Harada, N., Shiotani, S., Hiroshige, S., Soejima, Y., Suehiro, T., Sugimachi, K. Transplantation (2002) [Pubmed]
  19. 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. Yoshida, H., Sasaki, K., Namiki, Y., Sato, N., Tada, N. Atherosclerosis (2005) [Pubmed]
  20. The production of hydroxyl radicals in the fetal lamb brain resulting from occlusion of the umbilical circulation and the transplacental effect of MCI-186 to inhibit hydroxyl radical production. Nakajima, Y., Masaoka, N., Hayakawa, Y., Watanabe, M., Nagaishi, M., Sakata, H., Yamamoto, T. Pediatr. Res. (2006) [Pubmed]
  21. Lack of effect of influenza vaccine on the pharmacokinetics of antipyrine, alprazolam, paracetamol (acetaminophen) and lorazepam. Scavone, J.M., Blyden, G.T., Greenblatt, D.J. Clinical pharmacokinetics. (1989) [Pubmed]
  22. Alkoxyl radical-scavenging activity of edaravone in patients with traumatic brain injury. Dohi, K., Satoh, K., Mihara, Y., Nakamura, S., Miyake, Y., Ohtaki, H., Nakamachi, T., Yoshikawa, T., Shioda, S., Aruga, T. J. Neurotrauma (2006) [Pubmed]
  23. Metabolism of antipyrine in vivo in two rat models of liver cirrhosis. Its relationship to intrinsic clearance in vitro and microsomal membrane lipid composition. Buters, J.T., Zysset, T., Reichen, J. Biochem. Pharmacol. (1993) [Pubmed]
  24. A free radical scavenger but not FGF-2-mediated angiogenic therapy rescues myonephropathic metabolic syndrome in severe hindlimb ischemia. Kaneko, K., Yonemitsu, Y., Fujii, T., Onimaru, M., Jin, C.H., Inoue, M., Hasegawa, M., Onohara, T., Maehara, Y., Sueishi, K. Am. J. Physiol. Heart Circ. Physiol. (2006) [Pubmed]
  25. Protective effects of a free radical scavenger, MCI-186, on high-glucose-induced dysfunction of human dermal microvascular endothelial cells. Dong, J., Jiaojun, D., Takami, Y., Tanaka, H., Yamaguchi, R., Jingping, G., Chun, Q., Shuliang, L., Shimazaki, S., Ogo, K. Wound repair and regeneration : official publication of the Wound Healing Society [and] the European Tissue Repair Society. (2004) [Pubmed]
  26. Neuroprotective effects of edaravone: a novel free radical scavenger in cerebrovascular injury. Yoshida, H., Yanai, H., Namiki, Y., Fukatsu-Sasaki, K., Furutani, N., Tada, N. CNS drug reviews. (2006) [Pubmed]
  27. The hydroxyl radical scavenger MCI-186 protects the liver from experimental cold ischaemia-reperfusion injury. Ninomiya, M., Shimada, M., Harada, N., Soejima, Y., Suehiro, T., Maehara, Y. The British journal of surgery. (2004) [Pubmed]
  28. Free radical scavenger (edaravone) prevents endotoxin-induced liver injury after partial hepatectomy in rats. Tsuji, K., Kwon, A.H., Yoshida, H., Qiu, Z., Kaibori, M., Okumura, T., Kamiyama, Y. J. Hepatol. (2005) [Pubmed]
  29. A radical scavenger, edaravone, protects canine kidneys from ischemia-reperfusion injury after 72 hours of cold preservation and autotransplantation. Tahara, M., Nakayama, M., Jin, M.B., Fujita, M., Suzuki, T., Taniguchi, M., Shimamura, T., Furukawa, H., Todo, S. Transplantation (2005) [Pubmed]
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