Tirapazamine (BioDeep_00000732716)

   


代谢物信息卡片


Tirapazamine

化学式: C7H6N4O2 (178.0490736)
中文名称: 替拉扎明
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC=C2C(=C1)[N+](=C(N=[N+]2[O-])N)[O-]
InChI: InChI=1S/C7H6N4O2/c8-7-9-11(13)6-4-2-1-3-5(6)10(7)12/h1-4H,(H2,8,9)

描述信息

C274 - Antineoplastic Agent > C798 - Radiosensitizing Agent
D011838 - Radiation-Sensitizing Agents
D000970 - Antineoplastic Agents
C2077 - Bioreductive Agent

同义名列表

1 个代谢物同义名

Tirapazamine



数据库引用编号

7 个数据库交叉引用编号

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)

0 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

  • Zhouhui Wu, Yu Wang, Lei Li, Sihui Zhen, Heng Du, Zhiwen Wang, Shuang Xiao, Jinliang Wu, Lifei Zhu, Jiachen Shen, Zhen Wang. New insights into the antimicrobial action and protective therapeutic effect of tirapazamine towards Escherichia coli-infected mice. International journal of antimicrobial agents. 2023 Jul; ?(?):106923. doi: 10.1016/j.ijantimicag.2023.106923. [PMID: 37433388]
  • Yunxia Dong, Ling Zhou, Zijun Shen, Qingming Ma, Yifan Zhao, Yong Sun, Jie Cao. Iodinated cyanine dye-based nanosystem for synergistic phototherapy and hypoxia-activated bioreductive therapy. Drug delivery. 2022 Dec; 29(1):238-253. doi: 10.1080/10717544.2021.2023701. [PMID: 35001784]
  • Qing Li, Yiming Liu, Xiaopeng Guo, Lijie Zhang, Lin Li, Dan Zhao, Xin Zhang, Wei Hong, Chuansheng Zheng, Bin Liang. Tirapazamine-loaded CalliSpheres microspheres enhance synergy between tirapazamine and embolization against liver cancer in an animal model. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Jul; 151(?):113123. doi: 10.1016/j.biopha.2022.113123. [PMID: 35594702]
  • Vera L Silva, Amalia Ruiz, Ahlam Ali, Sara Pereira, Jani Seitsonen, Janne Ruokolainen, Fiona Furlong, Jonathan Coulter, Wafa' T Al-Jamal. Hypoxia-targeted cupric-tirapazamine liposomes potentiate radiotherapy in prostate cancer spheroids. International journal of pharmaceutics. 2021 Sep; 607(?):121018. doi: 10.1016/j.ijpharm.2021.121018. [PMID: 34416329]
  • Yihua Shi, Ming Gong, Zhouming Deng, Huifan Liu, Yiqiang Chang, Zhiqiang Yang, Lin Cai. Tirapazamine suppress osteosarcoma cells in part through SLC7A11 mediated ferroptosis. Biochemical and biophysical research communications. 2021 08; 567(?):118-124. doi: 10.1016/j.bbrc.2021.06.036. [PMID: 34147710]
  • Chang-Hsien Liu, Shih-Ming Kuo, Hong-Wei Gao, Yu-Juei Hsu. A rat toxicological study of intra-arterial injection of Tirapazamine, a hypoxia-activating Cancer therapeutic agent, followed by hepatic artery ligation. Investigational new drugs. 2021 06; 39(3):747-755. doi: 10.1007/s10637-020-01057-3. [PMID: 33428079]
  • Jing Chen, Xue Wang, Yuan Yuan, Haoting Chen, Lingpu Zhang, Haihua Xiao, Jingqi Chen, Yongxiang Zhao, Jin Chang, Weisheng Guo, Xing-Jie Liang. Exploiting the acquired vulnerability of cisplatin-resistant tumors with a hypoxia-amplifying DNA repair-inhibiting (HYDRI) nanomedicine. Science advances. 2021 03; 7(13):. doi: 10.1126/sciadv.abc5267. [PMID: 33771859]
  • Chris P Guise, Maria R Abbattista, Robert F Anderson, Dan Li, Rana Taghipouran, Angela Tsai, Su Jung Lee, Jeff B Smaill, William A Denny, Michael P Hay, William R Wilson, Kevin O Hicks, Adam V Patterson. Subcellular Location of Tirapazamine Reduction Dramatically Affects Aerobic but Not Anoxic Cytotoxicity. Molecules (Basel, Switzerland). 2020 Oct; 25(21):. doi: 10.3390/molecules25214888. [PMID: 33105798]
  • Ying Yang, Xue Yang, Huipeng Li, Chenzi Li, Huaqian Ding, Mengting Zhang, Yuxin Guo, Minjie Sun. Near-infrared light triggered liposomes combining photodynamic and chemotherapy for synergistic breast tumor therapy. Colloids and surfaces. B, Biointerfaces. 2019 Jan; 173(?):564-570. doi: 10.1016/j.colsurfb.2018.10.019. [PMID: 30347383]
  • Yanyan Liu, Yaqin Jiang, Meng Zhang, Zhongmin Tang, Mingyuan He, Wenbo Bu. Modulating Hypoxia via Nanomaterials Chemistry for Efficient Treatment of Solid Tumors. Accounts of chemical research. 2018 10; 51(10):2502-2511. doi: 10.1021/acs.accounts.8b00214. [PMID: 30234960]
  • Simon J A van Kuijk, Nanda Kumar Parvathaneni, Raymon Niemans, Marike W van Gisbergen, Fabrizio Carta, Daniela Vullo, Silvia Pastorekova, Ala Yaromina, Claudiu T Supuran, Ludwig J Dubois, Jean-Yves Winum, Philippe Lambin. New approach of delivering cytotoxic drugs towards CAIX expressing cells: A concept of dual-target drugs. European journal of medicinal chemistry. 2017 Feb; 127(?):691-702. doi: 10.1016/j.ejmech.2016.10.037. [PMID: 27823879]
  • Slawomir Mandziuk, Wlodzimierz Matysiak, Agnieszka Korga, Franciszek Burdan, Iwona Pasnik, Marcin Hejna, Agnieszka Korobowicz-Markiewicz, Luiza Grzycka-Kowalczyk, Michal Kowalczyk, Ewa Poleszak, Barbara Jodlowska-Jedrych, Jaroslaw Dudka. Tirapazamine has no Effect on Hepatotoxicity of Cisplatin and 5-fluorouracil but Interacts with Doxorubicin Leading to Side Changes in Redox Equilibrium. Basic & clinical pharmacology & toxicology. 2016 Sep; 119(3):330-40. doi: 10.1111/bcpt.12576. [PMID: 26990033]
  • Xi Liu, Yan Liu, Pengcheng Zhang, Xiaodong Jin, Xiaogang Zheng, Fei Ye, Weiqiang Chen, Qiang Li. The synergistic radiosensitizing effect of tirapazamine-conjugated gold nanoparticles on human hepatoma HepG2 cells under X-ray irradiation. International journal of nanomedicine. 2016; 11(?):3517-31. doi: 10.2147/ijn.s105348. [PMID: 27555772]
  • Quynh-Thu Le, Richard Fisher, Kelly S Oliner, Richard J Young, Hongbin Cao, Christina Kong, Edward Graves, Rodney J Hicks, Grant A McArthur, Lester Peters, Brian O'Sullivan, Amato Giaccia, Danny Rischin. Prognostic and predictive significance of plasma HGF and IL-8 in a phase III trial of chemoradiation with or without tirapazamine in locoregionally advanced head and neck cancer. Clinical cancer research : an official journal of the American Association for Cancer Research. 2012 Mar; 18(6):1798-807. doi: 10.1158/1078-0432.ccr-11-2094. [PMID: 22383739]
  • Annette M Lim, Danny Rischin, Richard Fisher, Hongbin Cao, Kathleen Kwok, Daniel Truong, Grant A McArthur, Richard J Young, Amato Giaccia, Lester Peters, Quynh-Thu Le. Prognostic significance of plasma osteopontin in patients with locoregionally advanced head and neck squamous cell carcinoma treated on TROG 02.02 phase III trial. Clinical cancer research : an official journal of the American Association for Cancer Research. 2012 Jan; 18(1):301-7. doi: 10.1158/1078-0432.ccr-11-2295. [PMID: 22096023]
  • Justyna Sliwinska, Jaroslaw Dudka, Agnieszka Korga, Franciszek Burdan, Wlodzimierz Matysiak, Barbara Jodlowska-Jedrych, Slawomir Mandziuk, Katarzyna Dawidek-Pietryka. Tirapazamine-doxorubicin interaction referring to heart oxidative stress and Ca²⁺ balance protein levels. Oxidative medicine and cellular longevity. 2012; 2012(?):890826. doi: 10.1155/2012/890826. [PMID: 22666522]
  • Kevin O Hicks, Bronwyn G Siim, Jagdish K Jaiswal, Frederik B Pruijn, Annie M Fraser, Rita Patel, Alison Hogg, H D Sarath Liyanage, Mary Jo Dorie, J Martin Brown, William A Denny, Michael P Hay, William R Wilson. Pharmacokinetic/pharmacodynamic modeling identifies SN30000 and SN29751 as tirapazamine analogues with improved tissue penetration and hypoxic cell killing in tumors. Clinical cancer research : an official journal of the American Association for Cancer Research. 2010 Oct; 16(20):4946-57. doi: 10.1158/1078-0432.ccr-10-1439. [PMID: 20732963]
  • Difeng Zhu, Jianshu Lou, Honghai Wu, Peihua Luo, Lanjuan Li. Correlation of pharmacokinetic features and tissue distribution with toxicity of Q39, a hypoxic cell cytotoxic agent. Die Pharmazie. 2010 Sep; 65(9):683-9. doi: NULL. [PMID: 21038846]
  • Edward E Graves, Amit Maity, Quynh-Thu Le. The tumor microenvironment in non-small-cell lung cancer. Seminars in radiation oncology. 2010 Jul; 20(3):156-63. doi: 10.1016/j.semradonc.2010.01.003. [PMID: 20685578]
  • C P Lee, G S Payne, A Oregioni, R Ruddle, S Tan, F I Raynaud, D Eaton, M J Campbell, K Cross, G Halbert, M Tracy, J McNamara, B Seddon, M O Leach, P Workman, I Judson. A phase I study of the nitroimidazole hypoxia marker SR4554 using 19F magnetic resonance spectroscopy. British journal of cancer. 2009 Dec; 101(11):1860-8. doi: 10.1038/sj.bjc.6605425. [PMID: 19935799]
  • D L Roberts, K J Williams, R L Cowen, M Barathova, A J Eustace, S Brittain-Dissont, M J Tilby, D G Pearson, C J Ottley, I J Stratford, C Dive. Contribution of HIF-1 and drug penetrance to oxaliplatin resistance in hypoxic colorectal cancer cells. British journal of cancer. 2009 Oct; 101(8):1290-7. doi: 10.1038/sj.bjc.6605311. [PMID: 19755992]
  • Andrea Kuemmerle, Laurent A Decosterd, Thierry Buclin, Danielle Liénard, Roger Stupp, Pierre-Guy Chassot, François Mosimann, Ferdy Lejeune. A phase I pharmacokinetic study of hypoxic abdominal stop-flow perfusion with gemcitabine in patients with advanced pancreatic cancer and refractory malignant ascites. Cancer chemotherapy and pharmacology. 2009 Jan; 63(2):331-41. doi: 10.1007/s00280-008-0743-5. [PMID: 18587581]
  • Michael P Hay, Kevin O Hicks, Karin Pchalek, Ho H Lee, Adrian Blaser, Frederik B Pruijn, Robert F Anderson, Sujata S Shinde, William R Wilson, William A Denny. Tricyclic [1,2,4]triazine 1,4-dioxides as hypoxia selective cytotoxins. Journal of medicinal chemistry. 2008 Nov; 51(21):6853-65. doi: 10.1021/jm800967h. [PMID: 18847185]
  • Philip C Mack, Mary W Redman, Kari Chansky, Stephen K Williamson, Nichole C Farneth, Primo N Lara, Wilbur A Franklin, Quynh-Thu Le, John J Crowley, David R Gandara. Lower osteopontin plasma levels are associated with superior outcomes in advanced non-small-cell lung cancer patients receiving platinum-based chemotherapy: SWOG Study S0003. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 2008 Oct; 26(29):4771-6. doi: 10.1200/jco.2008.17.0662. [PMID: 18779603]
  • R Scott Obach, Franco Lombardo, Nigel J Waters. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds. Drug metabolism and disposition: the biological fate of chemicals. 2008 Jul; 36(7):1385-405. doi: 10.1124/dmd.108.020479. [PMID: 18426954]
  • Mark De Ridder, Gretel Van Esch, Benedikt Engels, Valeri Verovski, Guy Storme. Hypoxic tumor cell radiosensitization: role of the iNOS/NO pathway. Bulletin du cancer. 2008 Mar; 95(3):282-91. doi: 10.1684/bdc.2008.0592. [PMID: 18390408]
  • Markus Adam, Christine Bayer, Julia Henke, Anca Grosu, Michael Molls, Carsten Nieder. Tirapazamine plus cisplatin and irradiation in a mouse model: improved tumor control at the cost of increased toxicity. Journal of cancer research and clinical oncology. 2008 Feb; 134(2):137-46. doi: 10.1007/s00432-007-0260-7. [PMID: 17622558]
  • M Bache, M Kappler, H M Said, A Staab, D Vordermark. Detection and specific targeting of hypoxic regions within solid tumors: current preclinical and clinical strategies. Current medicinal chemistry. 2008; 15(4):322-38. doi: 10.2174/092986708783497391. [PMID: 18288988]
  • Michael P Hay, Kevin O Hicks, Frederik B Pruijn, Karin Pchalek, Bronwyn G Siim, William R Wilson, William A Denny. Pharmacokinetic/pharmacodynamic model-guided identification of hypoxia-selective 1,2,4-benzotriazine 1,4-dioxides with antitumor activity: the role of extravascular transport. Journal of medicinal chemistry. 2007 Dec; 50(25):6392-404. doi: 10.1021/jm070670g. [PMID: 18001018]
  • Kevin O Hicks, Frederik B Pruijn, Timothy W Secomb, Michael P Hay, Richard Hsu, J Martin Brown, William A Denny, Mark W Dewhirst, William R Wilson. Use of three-dimensional tissue cultures to model extravascular transport and predict in vivo activity of hypoxia-targeted anticancer drugs. Journal of the National Cancer Institute. 2006 Aug; 98(16):1118-28. doi: 10.1093/jnci/djj306. [PMID: 16912264]
  • Markus Adam, Sigrid Ottenjann, Georg Künzel, Raymonde Busch, Wolf Erhardt, Carsten Nieder, Michael Molls. [Evaluation of the toxicity of tirapazamine plus cisplatin in a mouse tumor model]. Strahlentherapie und Onkologie : Organ der Deutschen Rontgengesellschaft ... [et al]. 2006 Apr; 182(4):231-9. doi: 10.1007/s00066-006-1506-z. [PMID: 16622625]
  • Hong Chen, Dan Zhang, Qingyuan Deng. [Study on HPLC determination method and pharmacokinetics of tirapazaming in rabbits]. Sheng wu yi xue gong cheng xue za zhi = Journal of biomedical engineering = Shengwu yixue gongchengxue zazhi. 2006 Feb; 23(1):180-3. doi: NULL. [PMID: 16532836]
  • M C E McFadyen, W T Melvin, G I Murray. Cytochrome P450 CYP1B1 activity in renal cell carcinoma. British journal of cancer. 2004 Aug; 91(5):966-71. doi: 10.1038/sj.bjc.6602053. [PMID: 15280921]
  • Peggy L Olive, Judit P Banáth, Laura T Sinnott. Phosphorylated histone H2AX in spheroids, tumors, and tissues of mice exposed to etoposide and 3-amino-1,2,4-benzotriazine-1,3-dioxide. Cancer research. 2004 Aug; 64(15):5363-9. doi: 10.1158/0008-5472.can-04-0729. [PMID: 15289343]
  • Bronwyn G Siim, Frederik B Pruijn, Joanna R Sturman, Alison Hogg, Michael P Hay, J Martin Brown, William R Wilson. Selective potentiation of the hypoxic cytotoxicity of tirapazamine by its 1-N-oxide metabolite SR 4317. Cancer research. 2004 Jan; 64(2):736-42. doi: 10.1158/0008-5472.can-03-2488. [PMID: 14744792]
  • Maria V Papadopoulou, William D Bloomer. NLCQ-1 (NSC 709257): exploiting hypoxia with a weak DNA-intercalating bioreductive drug. Clinical cancer research : an official journal of the American Association for Cancer Research. 2003 Nov; 9(15):5714-20. doi: NULL. [PMID: 14654556]
  • Primo N Lara, Paul Frankel, Philip C Mack, Paul H Gumerlock, Irina Galvin, Cynthia L Martel, Jeff Longmate, James H Doroshow, Heinz Josef Lenz, Derick H M Lau, David R Gandara. Tirapazamine plus carboplatin and paclitaxel in advanced malignant solid tumors: a california cancer consortium phase I and molecular correlative study. Clinical cancer research : an official journal of the American Association for Cancer Research. 2003 Oct; 9(12):4356-62. doi: NULL. [PMID: 14555506]
  • Shufeng Zhou, Philip Kestell, Bruce C Baguley, James W Paxton. 5,6-dimethylxanthenone-4-acetic acid (DMXAA): a new biological response modifier for cancer therapy. Investigational new drugs. 2002 Aug; 20(3):281-95. doi: 10.1023/a:1016215015530. [PMID: 12201491]
  • R D Blumenthal, A Taylor, L Osorio, R Ochakovskaya, J A Raleigh, M Papadopoulou, W D Bloomer, D M Goldenberg. Optimizing the use of combined radioimmunotherapy and hypoxic cytotoxin therapy as a function of tumor hypoxia. International journal of cancer. 2001 Nov; 94(4):564-71. doi: 10.1002/ijc.1500. [PMID: 11745445]
  • S Zhou, R Chin, P Kestell, M D Tingle, J W Paxton. Effects of anticancer drugs on the metabolism of the anticancer drug 5,6-dimethylxanthenone-4-acetic (DMXAA) by human liver microsomes. British journal of clinical pharmacology. 2001 Aug; 52(2):129-36. doi: 10.1046/j.0306-5251.2001.01438.x. [PMID: 11488768]
  • L N Shulman, L Buswell, N Riese, N Doherty, J S Loeffler, R W von Roemeling, C N Coleman. Phase I trial of the hypoxic cell cytotoxin tirapazamine with concurrent radiation therapy in the treatment of refractory solid tumors. International journal of radiation oncology, biology, physics. 1999 May; 44(2):349-53. doi: 10.1016/s0360-3016(99)00016-4. [PMID: 10760430]
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  • U Gatzemeier, G Rodriguez, J Treat, V Miller, R von Roemeling, J Viallet, A Rey. Tirapazamine-cisplatin: the synergy. British journal of cancer. 1998 Jun; 77 Suppl 4(?):15-7. doi: 10.1038/bjc.1998.431. [PMID: 9647615]
  • C A Johnson, D Kilpatrick, R von Roemeling, C Langer, M A Graham, D Greenslade, G Kennedy, E Keenan, P J O'Dwyer. Phase I trial of tirapazamine in combination with cisplatin in a single dose every 3 weeks in patients with solid tumors. Journal of clinical oncology : official journal of the American Society of Clinical Oncology. 1997 Feb; 15(2):773-80. doi: 10.1200/jco.1997.15.2.773. [PMID: 9053504]
  • M A Graham, S Senan, H Robin, N Eckhardt, D Lendrem, J Hincks, D Greenslade, R Rampling, S B Kaye, R von Roemeling, P Workman. Pharmacokinetics of the hypoxic cell cytotoxic agent tirapazamine and its major bioreductive metabolites in mice and humans: retrospective analysis of a pharmacokinetically guided dose-escalation strategy in a phase I trial. Cancer chemotherapy and pharmacology. 1997; 40(1):1-10. doi: 10.1007/s002800050617. [PMID: 9137522]
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  • H Robin, S Senan, P Workman, M A Graham. Development and validation of a sensitive solid-phase-extraction and high-performance liquid chromatography assay for the bioreductive agent tirapazamine and its major metabolites in mouse and human plasma for pharmacokinetically guided dose escalation. Cancer chemotherapy and pharmacology. 1995; 36(3):266-70. doi: 10.1007/bf00685859. [PMID: 7781150]
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  • M I Walton, P Workman. Pharmacokinetics and bioreductive metabolism of the novel benzotriazine di-N-oxide hypoxic cell cytotoxin tirapazamine (WIN 59075; SR 4233; NSC 130181) in mice. The Journal of pharmacology and experimental therapeutics. 1993 May; 265(2):938-47. doi: NULL. [PMID: 8496834]
  • I N White, A Cahill, A Davies, P Carthew. Acute lesions in rats caused by 3-amino-1,2,4-benzotriazine-1,4-dioxide (SR 4233) or nitromin: a comparison with rates of reduction in microsomal systems from target organs. Archives of toxicology. 1992; 66(2):100-6. doi: 10.1007/bf02342502. [PMID: 1605723]
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