Antipyrine (BioDeep_00000001556)
human metabolite blood metabolite Chemicals and Drugs
代谢物信息卡片
1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one
化学式: C11H12N2O (188.09495819999998)
中文名称: 安替比林
谱图信息:
最多检出来源 Homo sapiens(blood) 62.46%
分子结构信息
SMILES: CC1=CC(=O)N(N1C)C2=CC=CC=C2
InChI: InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3
描述信息
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)
N - Nervous system > N02 - Analgesics > N02B - Other analgesics and antipyretics > N02BB - Pyrazolones
S - Sensory organs > S02 - Otologicals > S02D - Other otologicals > S02DA - Analgesics and anesthetics
C78272 - Agent Affecting Nervous System > C241 - Analgesic Agent > C2198 - Nonnarcotic Analgesic
D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents
D002491 - Central Nervous System Agents > D000700 - Analgesics
D000893 - Anti-Inflammatory Agents
D018501 - Antirheumatic Agents
同义名列表
18 个代谢物同义名
1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one; 1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one; 2,3-Dimethyl-1-phenyl-5-pyrazolone; Antipyrinum; Pyramidone; Analgesine; Phenazonum; antipyrine; Phenozone; Azophenum; Phenazone; Antipyrin; Anodynine; Antipirin; Fenazona; Anodynin; Fenazone; Azophen
数据库引用编号
13 个数据库交叉引用编号
- ChEBI: CHEBI:31225
- KEGG: C13244
- PubChem: 2206
- HMDB: HMDB0015503
- Metlin: METLIN3931
- DrugBank: DB01435
- ChEMBL: CHEMBL277474
- Wikipedia: Antipyrine
- MeSH: Antipyrine
- chemspider: 2121
- CAS: 60-80-0
- PMhub: MS000000763
- PubChem: 585988
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
2 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Toru Yamashita, Koji Abe. Update on Antioxidant Therapy with Edaravone: Expanding Applications in Neurodegenerative Diseases.
International journal of molecular sciences.
2024 Mar; 25(5):. doi:
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2021 Nov; 44(6):927-936. doi:
10.1111/jvp.13003. [PMID: 34431528] - Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
Cell reports.
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2017 Nov; 19(6):639-646. doi:
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Drug delivery.
2017 Nov; 24(1):962-978. doi:
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Amyotrophic lateral sclerosis & frontotemporal degeneration.
2017 Oct; 18(sup1):71-79. doi:
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Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban.
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Oxidative medicine and cellular longevity.
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Clinical chemistry.
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Analytical and bioanalytical chemistry.
2016 Oct; 408(26):7403-11. doi:
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Biopharmaceutics & drug disposition.
2016 Sep; 37(6):373-8. doi:
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2015 Nov; 115(?):576-9. doi:
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2015 Jun; 34(6):654-61. doi:
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Analytical and bioanalytical chemistry.
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2015 Mar; 104(3):955-61. doi:
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Chinese medical journal.
2015 Jan; 128(2):203-9. doi:
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Oxidative medicine and cellular longevity.
2015; 2015(?):804659. doi:
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Oxidative medicine and cellular longevity.
2015; 2015(?):606981. doi:
10.1155/2015/606981. [PMID: 26557222] - Zujian Lan, Xiaoyu Xu, Wenkai Xu, Jin Li, Zengrong Liang, Xuefei Zhang, Ming Lei, Chunshun Zhao. Discovery of 3-n-butyl-2,3-dihydro-1H-isoindol-1-one as a potential anti-ischemic stroke agent.
Drug design, development and therapy.
2015; 9(?):3377-91. doi:
10.2147/dddt.s84731. [PMID: 26170623] - Huifang Cao, Ying Feng, Yunye Ning, Zinan Zhang, Weihao Li, Qiang Li. Edaravone protects rats and human pulmonary alveolar epithelial cells against hyperoxia injury: heme oxygenase-1 and PI3K/Akt pathway may be involved.
Experimental lung research.
2015; 41(7):404-14. doi:
10.3109/01902148.2015.1054053. [PMID: 26151294] - Ebru Emekli-Alturfan, Burçin Alev, Sevim Tunali, Sehkar Oktay, Tugba Tunali-Akbay, Leyla Koc Ozturk, Refiye Yanardag, Aysen Yarat. Effects of edaravone on cardiac damage in valproic acid induced toxicity.
Annals of clinical and laboratory science.
2015; 45(2):166-72. doi:
. [PMID: 25887870] - Chihiro Hayashi, Masahiro Ito, Ryoutaro Ito, Akiko Murakumo, Naoki Yamamoto, Noriko Hiramatsu, Ira J Fox, Akihiko Horiguchi. Effects of edaravone, a radical scavenger, on hepatocyte transplantation.
Journal of hepato-biliary-pancreatic sciences.
2014 Dec; 21(12):919-24. doi:
10.1002/jhbp.164. [PMID: 25205207] - Atsushi Tsuruoka, Chihiro Atsumi, Heisuke Mizukami, Takeshi Imai, Yuta Hagiwara, Yasuhiro Hasegawa. Effects of edaravone, a free radical scavenger, on circulating levels of MMP-9 and hemorrhagic transformation in patients with intravenous thrombolysis using low-dose alteplase.
Journal of stroke and cerebrovascular diseases : the official journal of National Stroke Association.
2014 Nov; 23(10):2894-2899. doi:
10.1016/j.jstrokecerebrovasdis.2014.07.022. [PMID: 25282183] - Dao-quan Tang, Xiao-xiao Zheng, Yin-jie Li, Ting-ting Bian, Yan-yan Yu, Qian Du, Dong-zhi Yang, Shui-shi Jiang. Two complementary liquid chromatography-tandem mass spectrometry (LC-MS/MS) methods to study the excretion and metabolic interaction of edaravone and taurine in rats.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2014 Nov; 970(?):8-17. doi:
10.1016/j.jchromb.2014.08.025. [PMID: 25222743] - Takashi Koyanagi, Yoshiyuki Yamaura, Koji Yano, Soonih Kim, Hiroshi Yamazaki. Age-related pharmacokinetic changes of acetaminophen, antipyrine, diazepam, diphenhydramine, and ofloxacin in male cynomolgus monkeys and beagle dogs.
Xenobiotica; the fate of foreign compounds in biological systems.
2014 Oct; 44(10):893-901. doi:
10.3109/00498254.2014.903532. [PMID: 24650193] - Jiangbei Yuan, Chengjian Wang, Yujiao Sun, Linjuan Huang, Zhongfu Wang. Nonreductive chemical release of intact N-glycans for subsequent labeling and analysis by mass spectrometry.
Analytical biochemistry.
2014 Oct; 462(?):1-9. doi:
10.1016/j.ab.2014.05.029. [PMID: 24912132] - Dao-quan Tang, Ting-ting Bian, Xiao-xiao Zheng, Ying Li, Xiao-wen Wu, Yin-jie Li, Qian Du, Shui-shi Jiang. LC-MS/MS methods for the determination of edaravone and/or taurine in rat plasma and its application to a pharmacokinetic study.
Biomedical chromatography : BMC.
2014 Sep; 28(9):1173-82. doi:
10.1002/bmc.3139. [PMID: 24706508] - Jing Qin, Ruo-Xi Zhang, Jia-Li Li, Jian-Xin Wang, Jia Hou, Xu Yang, Wei-Li Zhu, Jie Shi, Lin Lu. cRGD mediated liposomes enhanced antidepressant-like effects of edaravone in rats.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
2014 Jul; 58(?):63-71. doi:
10.1016/j.ejps.2014.03.006. [PMID: 24704101] - Zhi Chen, Jianbo Zhang, Qianwei Chen, Jing Guo, Gang Zhu, Hua Feng. Neuroprotective effects of edaravone after intraventricular hemorrhage in rats.
Neuroreport.
2014 Jun; 25(9):635-40. doi:
10.1097/wnr.0000000000000050. [PMID: 24169603] - Iu I Hubs'kyĭ, T A Bukhtiarova, H H Horiushko, N V Litvinova, H I Paramonova, T M Kurapova, O M Velychko, L P Babenko. [Biophysical parameters of erythrocyte membranes and mechanisms of interaction with non-opioid analgesics under acute pain syndrome].
Ukrainian biochemical journal.
2014 May; 86(3):98-106. doi:
". [PMID: 25033559] - Fahui Zhao, Zhigang Liu. Beneficial effects of edaravone on the expression of serum matrix metalloproteinase-9 after cerebral hemorrhage.
Neurosciences (Riyadh, Saudi Arabia).
2014 Apr; 19(2):106-10. doi:
. [PMID: 24739406] - L Zong, Q H Yu, Y X Du, X M Deng. Edaravone protects endotoxin-induced liver injury by inhibiting apoptosis and reducing proinflammatory cytokines.
Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas.
2014 Feb; 47(3):231-6. doi:
10.1590/1414-431x20133186. [PMID: 24554039] - Wen-Ting Rong, Ya-Peng Lu, Qing Tao, Miao Guo, Yu Lu, Yong Ren, Shu-Qin Yu. Hydroxypropyl-sulfobutyl-β-cyclodextrin improves the oral bioavailability of edaravone by modulating drug efflux pump of enterocytes.
Journal of pharmaceutical sciences.
2014 Feb; 103(2):730-42. doi:
10.1002/jps.23807. [PMID: 24311389] - Koki Harigaya, Hiroyuki Yamada, Shingo Horimoto, Hiroyuki Nishi, Jun Haginaka. Sensitive quantitation of residual phenylhydrazine in antipyrine by LC-ICP-MS with iodo derivatization.
Analytical sciences : the international journal of the Japan Society for Analytical Chemistry.
2014; 30(8):845-50. doi:
10.2116/analsci.30.845. [PMID: 25109648] - Zhouyang Wu, Yu Ming, Zhao Zhang, Jing Wu, Zhilin Wu, Shanglong Yao. Edaravone rescues the lung by inhibiting lipid peroxidation and pro-inflammatory cytokines in a rat model.
Chinese medical journal.
2014; 127(5):968-70. doi:
". [PMID: 24571896] - Yan-yan Yu, Xiao-xiao Zheng, Ting-ting Bian, Yin-jie Li, Xiao-wen Wu, Dong-zhi Yang, Shui-shi Jiang, Dao-quan Tang. Development and application of a LC-MS/MS assay for the simultaneous quantification of edaravone and taurine in beagle plasma.
Journal of separation science.
2013 Dec; 36(24):3837-44. doi:
10.1002/jssc.201300983. [PMID: 24133013] - Marie Nagai, Hisakazu Ohtani, Hiroki Satoh, Sayo Matsuoka, Satoko Hori, Tomoyuki Fujii, Yuji Taketani, Yasufumi Sawada. Characterization of transplacental transfer of paroxetine in perfused human placenta: development of a pharmacokinetic model to evaluate tapered dosing.
Drug metabolism and disposition: the biological fate of chemicals.
2013 Dec; 41(12):2124-32. doi:
10.1124/dmd.113.052332. [PMID: 24046332] - A Durán, J M Monteagudo, I Sanmartín, A Carrasco. Solar photo-Fenton mineralization of antipyrine in aqueous solution.
Journal of environmental management.
2013 Nov; 130(?):64-71. doi:
10.1016/j.jenvman.2013.08.043. [PMID: 24064141] - Masahiro Kamouchi, Hironori Sakai, Yutaka Kiyohara, Kazuo Minematsu, Kunihiko Hayashi, Takanari Kitazono. Acute kidney injury and edaravone in acute ischemic stroke: the Fukuoka Stroke Registry.
Journal of stroke and cerebrovascular diseases : the official journal of National Stroke Association.
2013 Nov; 22(8):e470-6. doi:
10.1016/j.jstrokecerebrovasdis.2013.05.018. [PMID: 23800495] - Huaizhong Guo, Fang Wu, Weiquan Zhang, Fangli Liu. [Identification of traditional Chinese medicines by oligosaccharide electrophoresis analysis assisted with cluster analysis].
Se pu = Chinese journal of chromatography.
2013 Oct; 31(10):1001-4. doi:
10.3724/sp.j.1123.2013.03033. [PMID: 24432644] - Lucas Actis-Goretta, Antoine Lévèques, Maarit Rein, Alexander Teml, Christian Schäfer, Ute Hofmann, Hequn Li, Matthias Schwab, Michel Eichelbaum, Gary Williamson. Intestinal absorption, metabolism, and excretion of (-)-epicatechin in healthy humans assessed by using an intestinal perfusion technique.
The American journal of clinical nutrition.
2013 Oct; 98(4):924-33. doi:
10.3945/ajcn.113.065789. [PMID: 23864538] - Guoming Zhang, Yuanyuan Sun, Yu Wang, Xiaoyan Li, Tiande Li, Shaoping Su, Lin Xu, Hong Shen. Local administration of lactic acid and a low dose of the free radical scavenger, edaravone, alleviates myocardial reperfusion injury in rats.
Journal of cardiovascular pharmacology.
2013 Oct; 62(4):369-78. doi:
10.1097/01.fjc.0000432860.48345.9d. [PMID: 23884160] - Guo-ming Zhang, Yu Wang, Xiao-yan Li, Lin Xu, Yuan-yuan Sun, Yu-zhen Li, Li-feng Liu. [Pharmacological postconditioning with lactic acid and low dose edaravone could attenuate myocardial reperfusion injury through mitochondrial pathway].
Zhonghua xin xue guan bing za zhi.
2013 Aug; 41(8):647-53. doi:
NULL. [PMID: 24225235] - Raja Ghosh, Si Pan, Lijuan Wang, Simon Lu. A pulsed tangential-flow ultrafiltration technique for studying protein-drug binding.
Journal of pharmaceutical sciences.
2013 Aug; 102(8):2679-88. doi:
10.1002/jps.23639. [PMID: 23765403] - A Anadón, M A Martínez, M Martínez, V Castellano, I Ares, A Romero, R Fernández, M R Martínez-Larrañaga. Differential induction of cytochrome P450 isoforms and peroxisomal proliferation by cyfluthrin in male Wistar rats.
Toxicology letters.
2013 Jul; 220(2):135-42. doi:
10.1016/j.toxlet.2013.04.015. [PMID: 23639246] - Gui-lian Zhang, Wang-gang Zhang, Yun Du, Li Yao, Hong Sun, Ru Zhang, Enqi Liu, Ning Bu, Hai-qin Wu, Lei Zhang, Ting-ting Li, Ying-ying Guo. Edaravone ameliorates oxidative damage associated with Aβ25-35 treatment in PC12 cells.
Journal of molecular neuroscience : MN.
2013 Jul; 50(3):494-503. doi:
10.1007/s12031-013-9973-z. [PMID: 23393032] - Wang Qingsong, Guan Yeming, Liu Xuechun, Liu Hongjuan, Wang Jing. The free radical scavenger, edaravone, ameliorates delayed neuropsychological sequelae after acute carbon monoxide poisoning in rabbits.
Undersea & hyperbaric medicine : journal of the Undersea and Hyperbaric Medical Society, Inc.
2013 May; 40(3):223-9. doi:
. [PMID: 23789557] - Weiwei Zhang, Yongqing Guo, Shuzhen Yu, Jianfeng Wei, Jianmin Jin. Effects of edaravone on the expression of β-defensin-2 mRNA in lung tissue of rats with myocardial ischemia reperfusion.
Molecular medicine reports.
2013 May; 7(5):1683-7. doi:
10.3892/mmr.2013.1393. [PMID: 23525405] - Wensi Lin, Jianmei Zhang, Xiaomei Ling, Ning Yu, Jing Li, Haisong Yang, Runtao Li, Jingrong Cui. Evaluation of the effect of TM208 on the activity of five cytochrome P450 enzymes using on-line solid-phase extraction HPLC-DAD: a cocktail approach.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2013 Apr; 923-924(?):29-36. doi:
10.1016/j.jchromb.2013.01.031. [PMID: 23466445] - Kazuichiro Hori, Masaya Tsujii, Takahiro Iino, Haruhiko Satonaka, Takeshi Uemura, Koji Akeda, Masahiro Hasegawa, Atsumasa Uchida, Akihiro Sudo. Protective effect of edaravone for tourniquet-induced ischemia-reperfusion injury on skeletal muscle in murine hindlimb.
BMC musculoskeletal disorders.
2013 Mar; 14(?):113. doi:
10.1186/1471-2474-14-113. [PMID: 23530927] - Guang-Yi Li, Yong Feng, Tak S Cheng, Ji-Min Yin, Chang-Qing Zhang. Edaravone, a novel free radical scavenger, prevents steroid-induced osteonecrosis in rabbits.
Rheumatology (Oxford, England).
2013 Mar; 52(3):438-47. doi:
10.1093/rheumatology/kes313. [PMID: 23173187] - Markku Kaste, Satoru Murayama, Gary A Ford, Diederik W J Dippel, Matthew R Walters, Turgut Tatlisumak. Safety, tolerability and pharmacokinetics of MCI-186 in patients with acute ischemic stroke: new formulation and dosing regimen.
Cerebrovascular diseases (Basel, Switzerland).
2013; 36(3):196-204. doi:
10.1159/000353680. [PMID: 24135530] - Mete Ergenoglu, Oytun Erbaş, Ali Akdemir, Ahmet Özgür Yeniel, Nuri Yildirim, Fatih Oltulu, Hüseyin Aktuğ, Dilek Taskiran. Attenuation of ischemia/reperfusion-induced ovarian damage in rats: does edaravone offer protection?.
European surgical research. Europaische chirurgische Forschung. Recherches chirurgicales europeennes.
2013; 51(1-2):21-32. doi:
10.1159/000353403. [PMID: 23899611] - Tomoko Somekawa-Kondo, Keitaro Yamaguchi, Yoichi Ishitsuka, Sachiko Ito, Kaori Tanaka, Mitsuru Irikura, Hiroshi Moriuchi, Kazuo Takahama, Yukio Ando, Toshio Yamazaki, Tetsumi Irie. Aminophylline, administered at usual doses for rodents in pharmacological studies, induces hippocampal neuronal cell injury under low tidal volume hypoxic conditions in guinea-pigs.
The Journal of pharmacy and pharmacology.
2013 Jan; 65(1):102-14. doi:
10.1111/j.2042-7158.2012.01566.x. [PMID: 23215693] - Daniel J Warner, Hongming Chen, Louis-David Cantin, J Gerry Kenna, Simone Stahl, Clare L Walker, Tobias Noeske. Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.
Drug metabolism and disposition: the biological fate of chemicals.
2012 Dec; 40(12):2332-41. doi:
10.1124/dmd.112.047068. [PMID: 22961681] - Yoshiki Matsuda, Yoshihiro Konno, Masahiro Satsukawa, Taro Kobayashi, Yu Takimoto, Kunihiko Morisaki, Shinji Yamashita. Assessment of intestinal availability of various drugs in the oral absorption process using portal vein-cannulated rats.
Drug metabolism and disposition: the biological fate of chemicals.
2012 Dec; 40(12):2231-8. doi:
10.1124/dmd.112.048223. [PMID: 22930277] - Kazunori Iwanaga, Mineo Kawai, Makoto Miyazaki, Masawo Kakemi. Application of organogels as oral controlled release formulations of hydrophilic drugs.
International journal of pharmaceutics.
2012 Oct; 436(1-2):869-72. doi:
10.1016/j.ijpharm.2012.06.041. [PMID: 22766444] - Somasundaram Arumugam, Rajarajan A Thandavarayan, Punniyakoti T Veeraveedu, Vijayasree V Giridharan, Vivian Soetikno, Meilei Harima, Kenji Suzuki, Masaki Nagata, Ritsuo Tagaki, Makoto Kodama, Kenichi Watanabe. Involvement of AMPK and MAPK signaling during the progression of experimental autoimmune myocarditis in rats and its blockade using a novel antioxidant.
Experimental and molecular pathology.
2012 Oct; 93(2):183-9. doi:
10.1016/j.yexmp.2012.04.012. [PMID: 22542793] - Panagiota Tsounapi, Motoaki Saito, Fotios Dimitriadis, Sotirios Koukos, Shogo Shimizu, Keisuke Satoh, Atsushi Takenaka, Nikolaos Sofikitis. Antioxidant treatment with edaravone or taurine ameliorates diabetes-induced testicular dysfunction in the rat.
Molecular and cellular biochemistry.
2012 Oct; 369(1-2):195-204. doi:
10.1007/s11010-012-1382-z. [PMID: 22763673] - Laura Monturiol-Gross, Marietta Flores-Díaz, Cindy Araya-Castillo, María-José Pineda-Padilla, Graeme C Clark, Richard W Titball, Alberto Alape-Girón. Reactive oxygen species and the MEK/ERK pathway are involved in the toxicity of clostridium perfringens α-toxin, a prototype bacterial phospholipase C.
The Journal of infectious diseases.
2012 Oct; 206(8):1218-26. doi:
10.1093/infdis/jis496. [PMID: 22904339]