Dexrazoxane (BioDeep_00000027049)

human metabolite blood metabolite Chemicals and Drugs

代谢物信息卡片

4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione

化学式: C11H16N4O4 (268.1171496)
中文名称: 右雷佐生, 丙亚胺, 雷佐生
谱图信息: 最多检出来源 Homo sapiens(blood) 87.5%

分子结构信息

SMILES: CC(CN1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1
InChI: InChI=1S/C11H16N4O4/c1-7(15-5-10(18)13-11(19)6-15)2-14-3-8(16)12-9(17)4-14/h7H,2-6H2,1H3,(H,12,16,17)(H,13,18,19)

描述信息

An antimitotic agent with immunosuppressive properties. Dexrazoxane, the (+)-enantiomorph of razoxane, provides cardioprotection against anthracycline toxicity. It appears to inhibit formation of a toxic iron-anthracycline complex. [PubChem]. The Food and Drug Administration has designated dexrazoxane as an orphan drug for use in the prevention or reduction in the incidence and severity of anthracycline-induced cardiomyopathy.
V - Various > V03 - All other therapeutic products > V03A - All other therapeutic products > V03AF - Detoxifying agents for antineoplastic treatment
D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059005 - Topoisomerase II Inhibitors
D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents > D054659 - Diketopiperazines
D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents
D020011 - Protective Agents > D002316 - Cardiotonic Agents
D002317 - Cardiovascular Agents
D050258 - Mitosis Modulators
D004791 - Enzyme Inhibitors

同义名列表

21 个代谢物同义名

4-[(2S)-2-(3,5-dioxopiperazin-1-yl)propyl]piperazine-2,6-dione; (+)-(S)-4,4-Propylenedi-2,6-piperazinedione; (+)-1,2-Bis(3,5-dioxo-1-piperazinyl)propane; Razoxane, (S)-isomer, hydrochloride; Hydrochloride, dexrazoxane; Dexrazoxane hydrochloride; Razoxane, (S)-isomer; Dextrorazoxane; Dexrazoxanum; Desrazoxane; Dexrazoxano; Dexrazoxane; Cardioxane; Cardioxan; ICRF 187; Zinecard; Razoxane; Icrf-187; ICRF187; ADR 529; ADR-529

数据库引用编号

18 个数据库交叉引用编号

ChEBI: CHEBI:50225
ChEBI: CHEBI:50223
KEGG: C74037
PubChem: 30623
PubChem: 71384
HMDB: HMDB0014524
DrugBank: DB00380
ChEMBL: CHEMBL444186
ChEMBL: CHEMBL1738
Wikipedia: Dexrazoxane
MeSH: Dexrazoxane
MeSH: Razoxane
chemspider: 64479
CAS: 83713-23-9
CAS: 24584-09-6
CAS: 21416-87-5
CAS: 21416-67-1
PMhub: MS000242041

分类词条

Alpha amino acids and derivatives

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)

1 个相关的物种来源信息

9606 - Homo sapiens: -

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

Zhimin Mao, Kun Zhong, Xiaojun Liu, Xuhui Zeng. Ferroptosis contributes to cyclophosphamide-induced hemorrhagic cystitis. Chemico-biological interactions. 2023 Sep; ?(?):110701. doi: 10.1016/j.cbi.2023.110701. [PMID: 37690746]
Linfeng Zou, Bing Liang, YuanZhen Gao, Ting Ye, MengJiao Li, Yukun Zhang, Qi Lu, Xiaokun Hu, Huanting Li, Yang Yuan, Dongming Xing. Nicotinic Acid Riboside Regulates Nrf-2/P62-Related Oxidative Stress and Autophagy to Attenuate Doxorubicin-Induced Cardiomyocyte Injury. BioMed research international. 2022; 2022(?):6293329. doi: 10.1155/2022/6293329. [PMID: 35242876]
Huihui Hu, Caipeng Xie, Zeping Weng, Pei Yu, Yuqiang Wang, Luchen Shan. Dexrazoxane Alleviated Doxorubicin-Induced Nephropathy in Rats. Pharmacology. 2022; 107(3-4):206-215. doi: 10.1159/000521220. [PMID: 35021174]
Hana Bavlovič Piskáčková, Hana Jansová, Jan Kubeš, Galina Karabanovich, Nela Váňová, Petra Kollárová-Brázdová, Iuliia Melnikova, Anna Jirkovská, Olga Lenčová-Popelová, Jaroslav Chládek, Jaroslav Roh, Tomáš Šimůnek, Martin Štěrba, Petra Štěrbová-Kovaříková. Development of water-soluble prodrugs of the bisdioxopiperazine topoisomerase IIβ inhibitor ICRF-193 as potential cardioprotective agents against anthracycline cardiotoxicity. Scientific reports. 2021 02; 11(1):4456. doi: 10.1038/s41598-021-83688-x. [PMID: 33627707]
Long Li, Xiaoqi Nie, Peng Zhang, Yongbiao Huang, Li Ma, Fang Li, Minxiao Yi, Wan Qin, Xianglin Yuan. Dexrazoxane ameliorates radiation-induced heart disease in a rat model. Aging. 2021 01; 13(3):3699-3711. doi: 10.18632/aging.202332. [PMID: 33406500]
Petra Reimerová, Anna Jirkovská, Hana Bavlovič Piskáčková, Galina Karabanovich, Jaroslav Roh, Tomáš Šimůnek, Petra Štěrbová-Kovaříková. UHPLC-MS/MS method for analysis of sobuzoxane, its active form ICRF-154 and metabolite EDTA-diamide and its application to bioactivation study. Scientific reports. 2019 03; 9(1):4524. doi: 10.1038/s41598-019-40928-5. [PMID: 30872754]
Varsha G Desai, Taewon Lee, Carrie L Moland, Vikrant Vijay, Tao Han, Sherry M Lewis, Eugene H Herman, James C Fuscoe. Candidate early predictive plasma protein markers of doxorubicin-induced chronic cardiotoxicity in B6C3F1 mice. Toxicology and applied pharmacology. 2019 01; 363(?):164-173. doi: 10.1016/j.taap.2018.11.016. [PMID: 30517846]
Eduard Jirkovský, Anna Jirkovská, Jan Bureš, Jaroslav Chládek, Olga Lenčová, Ján Stariat, Zuzana Pokorná, Galina Karabanovich, Jaroslav Roh, Petra Brázdová, Tomáš Šimůnek, Petra Kovaříková, Martin Štěrba. Pharmacokinetics of the Cardioprotective Drug Dexrazoxane and Its Active Metabolite ADR-925 with Focus on Cardiomyocytes and the Heart. The Journal of pharmacology and experimental therapeutics. 2018 03; 364(3):433-446. doi: 10.1124/jpet.117.244848. [PMID: 29273587]
Joyce H Lee, Timothy J Wendorff, James M Berger. Resveratrol: A novel type of topoisomerase II inhibitor. The Journal of biological chemistry. 2017 12; 292(51):21011-21022. doi: 10.1074/jbc.m117.810580. [PMID: 29074616]
Sabry M Attia, Ali Y Alshahrani, Mohammed A Al-Hamamah, Mohammed M Attia, Quaiser Saquib, Sheikh F Ahmad, Mushtaq A Ansari, Ahmed Nadeem, Saleh A Bakheet. Dexrazoxane Averts Idarubicin-Evoked Genomic Damage by Regulating Gene Expression Profiling Associated With the DNA Damage-Signaling Pathway in BALB/c Mice. Toxicological sciences : an official journal of the Society of Toxicology. 2017 Nov; 160(1):161-172. doi: 10.1093/toxsci/kfx161. [PMID: 28973540]
Yang QuanJun, Yang GenJin, Wan LiLi, Han YongLong, Huo Yan, Li Jie, Huang JinLu, Lu Jin, Gan Run, Guo Cheng. Protective Effects of Dexrazoxane against Doxorubicin-Induced Cardiotoxicity: A Metabolomic Study. PloS one. 2017; 12(1):e0169567. doi: 10.1371/journal.pone.0169567. [PMID: 28072830]
Anna Tycova, Marek Vido, Petra Kovarikova, Frantisek Foret. Interface-free capillary electrophoresis-mass spectrometry system with nanospray ionization-Analysis of dexrazoxane in blood plasma. Journal of chromatography. A. 2016 Sep; 1466(?):173-9. doi: 10.1016/j.chroma.2016.08.042. [PMID: 27613146]
Vikrant Vijay, Carrie L Moland, Tao Han, James C Fuscoe, Taewon Lee, Eugene H Herman, G Ronald Jenkins, Sherry M Lewis, Connie A Cummings, Yuan Gao, Zhijun Cao, Li-Rong Yu, Varsha G Desai. Early transcriptional changes in cardiac mitochondria during chronic doxorubicin exposure and mitigation by dexrazoxane in mice. Toxicology and applied pharmacology. 2016 Mar; 295(?):68-84. doi: 10.1016/j.taap.2016.02.003. [PMID: 26873546]
Olga Lenčová-Popelová, Eduard Jirkovský, Hana Jansová, Anna Jirkovská-Vávrová, Lucie Vostatková-Tichotová, Yvona Mazurová, Michaela Adamcová, Jaroslav Chládek, Miloš Hroch, Zuzana Pokorná, Vladimír Geršl, Tomáš Šimůnek, Martin Štěrba. Cardioprotective effects of inorganic nitrate/nitrite in chronic anthracycline cardiotoxicity: Comparison with dexrazoxane. Journal of molecular and cellular cardiology. 2016 Feb; 91(?):92-103. doi: 10.1016/j.yjmcc.2015.12.021. [PMID: 26724189]
Pranitha Kamat, Stijn Vandenberghe, Stephan Christen, Anjan K Bongoni, Bernhard Meier, Robert Rieben, Ahmed A Khattab. Dexrazoxane Shows No Protective Effect in the Acute Phase of Reperfusion during Myocardial Infarction in Pigs. PloS one. 2016; 11(12):e0168541. doi: 10.1371/journal.pone.0168541. [PMID: 28002439]
Fangyi Sun, Xiaoyong Qi, Cuizhi Geng, Xingtao Li. Dexrazoxane protects breast cancer patients with diabetes from chemotherapy-induced cardiotoxicity. The American journal of the medical sciences. 2015 May; 349(5):406-12. doi: 10.1097/maj.0000000000000432. [PMID: 25723884]
Sheng Zhang, Tingting Meng, Jingjing Liu, Xiaobei Zhang, Jin Zhang. Cardiac protective effects of dexrazoxane on animal cardiotoxicity model induced by anthracycline combined with trastuzumab is associated with upregulation of calpain-2. Medicine. 2015 Jan; 94(4):e445. doi: 10.1097/md.0000000000000445. [PMID: 25634181]
Jolana Cermanova, Zuzana Kadova, Eva Dolezelova, Marie Zagorova, Vaclav Safka, Milos Hroch, Tomas Laho, Magdalena Holeckova, Jaroslav Mokry, Petra Kovarikova, Jan Bures, Martin Sterba, Stanislav Micuda. Deferoxamine but not dexrazoxane alleviates liver injury induced by endotoxemia in rats. Shock (Augusta, Ga.). 2014 Oct; 42(4):372-9. doi: 10.1097/shk.0000000000000210. [PMID: 25140599]
Yoshihiko Ichikawa, Mohsen Ghanefar, Marina Bayeva, Rongxue Wu, Arineh Khechaduri, Sathyamangla V Naga Prasad, R Kannan Mutharasan, Tejaswitha Jairaj Naik, Hossein Ardehali. Cardiotoxicity of doxorubicin is mediated through mitochondrial iron accumulation. The Journal of clinical investigation. 2014 Feb; 124(2):617-30. doi: 10.1172/jci72931. [PMID: 24382354]
Petra Kovarikova, Ivana Pasakova-Vrbatova, Anna Vavrova, Jan Stariat, Jiri Klimes, Tomas Simunek. Development of LC-MS/MS method for the simultaneous analysis of the cardioprotective drug dexrazoxane and its metabolite ADR-925 in isolated cardiomyocytes and cell culture medium. Journal of pharmaceutical and biomedical analysis. 2013 Mar; 76(?):243-51. doi: 10.1016/j.jpba.2012.12.024. [PMID: 23339990]
Jennifer S Dickey, Yanira Gonzalez, Baikuntha Aryal, Steven Mog, Asako J Nakamura, Christophe E Redon, Ulrich Baxa, Elliot Rosen, Gang Cheng, Jacek Zielonka, Palak Parekh, Karen P Mason, Joy Joseph, Balaraman Kalyanaraman, William Bonner, Eugene Herman, Emily Shacter, V Ashutosh Rao. Mito-tempol and dexrazoxane exhibit cardioprotective and chemotherapeutic effects through specific protein oxidation and autophagy in a syngeneic breast tumor preclinical model. PloS one. 2013; 8(8):e70575. doi: 10.1371/journal.pone.0070575. [PMID: 23940596]
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Pavlína Hašková, Lucie Koubková, Anna Vávrová, Eliška Macková, Kateřina Hrušková, Petra Kovaříková, Kateřina Vávrová, Tomáš Simůnek. Comparison of various iron chelators used in clinical practice as protecting agents against catecholamine-induced oxidative injury and cardiotoxicity. Toxicology. 2011 Nov; 289(2-3):122-31. doi: 10.1016/j.tox.2011.08.006. [PMID: 21864640]
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Patricia E Schroeder, Gu-Qi Wang, Frank J Burczynski, Brian B Hasinoff. Metabolism of the cardioprotective drug dexrazoxane and one of its metabolites by isolated rat myocytes, hepatocytes, and blood. Drug metabolism and disposition: the biological fate of chemicals. 2005 Jun; 33(6):719-25. doi: 10.1124/dmd.104.003186. [PMID: 15764716]
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