Triapine (BioDeep_00000654272)
代谢物信息卡片
Triapine
化学式: C7H9N5S (195.0578634)
中文名称: 2-[(3-氨基吡啶-2-基)亚甲基]氨基硫脲, [(3-氨基吡啶-2-基)亚甲基氨基]硫脲, Triapine
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1=CC(=C(N=C1)C=NNC(=S)N)N
InChI: InChI=1S/C7H9N5S/c8-5-2-1-3-10-6(5)4-11-12-7(9)13/h1-4H,8H2,(H3,9,12,13)/b11-4+
数据库引用编号
6 个数据库交叉引用编号
- PubChem: 9571836
- DrugBank: DB11940
- ChEMBL: CHEMBL231616
- CAS: 200933-27-3
- CAS: 236392-56-6
- CAS: 143621-35-6
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
- Nóra V May, Attila Jancsó, Éva A Enyedy. Binding Models of Copper(II) Thiosemicarbazone Complexes with Human Serum Albumin: A Speciation Study.
Molecules (Basel, Switzerland).
2021 May; 26(9):. doi:
10.3390/molecules26092711. [PMID: 34063080] - Kateryna Ohui, Iryna Stepanenko, Iuliana Besleaga, Maria V Babak, Radu Stafi, Denisa Darvasiova, Gerald Giester, Vivien Pósa, Eva A Enyedy, Daniel Vegh, Peter Rapta, Wee Han Ang, Ana Popović-Bijelić, Vladimir B Arion. Triapine Derivatives Act as Copper Delivery Vehicles to Induce Deadly Metal Overload in Cancer Cells.
Biomolecules.
2020 09; 10(9):. doi:
10.3390/biom10091336. [PMID: 32961653] - Karla Pelivan, Lisa M Frensemeier, Uwe Karst, Gunda Koellensperger, Petra Heffeter, Bernhard K Keppler, Christian R Kowol. Comparison of metabolic pathways of different α-N-heterocyclic thiosemicarbazones.
Analytical and bioanalytical chemistry.
2018 Mar; 410(9):2343-2361. doi:
10.1007/s00216-018-0889-x. [PMID: 29476231] - Marta Rejmund, Anna Mrozek-Wilczkiewicz, Katarzyna Malarz, Monika Pyrkosz-Bulska, Kamila Gajcy, Mieczyslaw Sajewicz, Robert Musiol, Jaroslaw Polanski. Piperazinyl fragment improves anticancer activity of Triapine.
PloS one.
2018; 13(4):e0188767. doi:
10.1371/journal.pone.0188767. [PMID: 29652894] - Julia Matsumoto, Brian F Kiesel, Robert A Parise, Jianxia Guo, Sarah Taylor, Marilyn Huang, Julie L Eiseman, S Percy Ivy, Charles Kunos, Edward Chu, Jan H Beumer. LC-MS/MS assay for the quantitation of the ribonucleotide reductase inhibitor triapine in human plasma.
Journal of pharmaceutical and biomedical analysis.
2017 Nov; 146(?):154-160. doi:
10.1016/j.jpba.2017.08.036. [PMID: 28881312] - Karla Pelivan, Lisa Frensemeier, Uwe Karst, Gunda Koellensperger, Bjoern Bielec, Sonja Hager, Petra Heffeter, Bernhard K Keppler, Christian R Kowol. Understanding the metabolism of the anticancer drug Triapine: electrochemical oxidation, microsomal incubation and in vivo analysis using LC-HRMS.
The Analyst.
2017 Aug; 142(17):3165-3176. doi:
10.1039/c7an00902j. [PMID: 28745337] - Walter Miklos, Petra Heffeter, Christine Pirker, Sonja Hager, Christian R Kowol, Sushilla van Schoonhoven, Mirjana Stojanovic, Bernhard K Keppler, Walter Berger. Loss of phosphodiesterase 4D mediates acquired triapine resistance via Epac-Rap1-Integrin signaling.
Oncotarget.
2016 Dec; 7(51):84556-84574. doi:
10.18632/oncotarget.11821. [PMID: 27602951] - Karla Pelivan, Walter Miklos, Sushilla van Schoonhoven, Gunda Koellensperger, Lars Gille, Walter Berger, Petra Heffeter, Christian R Kowol, Bernhard K Keppler. Differences in protein binding and excretion of Triapine and its Fe(III) complex.
Journal of inorganic biochemistry.
2016 07; 160(?):61-9. doi:
10.1016/j.jinorgbio.2015.10.006. [PMID: 26507768] - Ye Feng, Charles A Kunos, Yan Xu. Determination of triapine, a ribonucleotide reductase inhibitor, in human plasma by liquid chromatography tandem mass spectrometry.
Biomedical chromatography : BMC.
2015 Sep; 29(9):1380-7. doi:
10.1002/bmc.3434. [PMID: 25677991] - Jill Kolesar, Richard C Brundage, Marcia Pomplun, Dona Alberti, Kyle Holen, Anne Traynor, Percy Ivy, George Wilding. Population pharmacokinetics of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (Triapine®) in cancer patients.
Cancer chemotherapy and pharmacology.
2011 Feb; 67(2):393-400. doi:
10.1007/s00280-010-1331-z. [PMID: 20440618] - Charles A Kunos, Steven Waggoner, Vivian von Gruenigen, Elisa Eldermire, John Pink, Afshin Dowlati, Timothy J Kinsella. Phase I trial of pelvic radiation, weekly cisplatin, and 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, NSC #663249) for locally advanced cervical cancer.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2010 Feb; 16(4):1298-306. doi:
10.1158/1078-0432.ccr-09-2469. [PMID: 20145183] - Valery M Nelson, Chantée M Dancik, Weiying Pan, Zhi-Gang Jiang, Michael S Lebowitz, Hossein A Ghanbari. PAN-811 inhibits oxidative stress-induced cell death of human Alzheimer's disease-derived and age-matched olfactory neuroepithelial cells via suppression of intracellular reactive oxygen species.
Journal of Alzheimer's disease : JAD.
2009; 17(3):611-9. doi:
10.3233/jad-2009-1078. [PMID: 19433896] - Brigette Ma, Boon Cher Goh, Eng Huat Tan, Kwok Chi Lam, Ross Soo, Swan Swan Leong, Ling Zhi Wang, Frankie Mo, Anthony T C Chan, Benny Zee, Tony Mok. A multicenter phase II trial of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP, Triapine) and gemcitabine in advanced non-small-cell lung cancer with pharmacokinetic evaluation using peripheral blood mononuclear cells.
Investigational new drugs.
2008 Apr; 26(2):169-73. doi:
10.1007/s10637-007-9085-0. [PMID: 17851637] - Jennifer J Knox, Sebastien J Hotte, Christian Kollmannsberger, Eric Winquist, Bryn Fisher, Elizabeth A Eisenhauer. Phase II study of Triapine in patients with metastatic renal cell carcinoma: a trial of the National Cancer Institute of Canada Clinical Trials Group (NCIC IND.161).
Investigational new drugs.
2007 Oct; 25(5):471-7. doi:
10.1007/s10637-007-9044-9. [PMID: 17393073] - Ivana Gojo, Michael L Tidwell, Jacqueline Greer, Naoko Takebe, Karen Seiter, Mary F Pochron, Bonny Johnson, Mario Sznol, Judith E Karp. Phase I and pharmacokinetic study of Triapine, a potent ribonucleotide reductase inhibitor, in adults with advanced hematologic malignancies.
Leukemia research.
2007 Sep; 31(9):1165-73. doi:
10.1016/j.leukres.2007.01.004. [PMID: 17324462] - Yun Yen, Kim Margolin, James Doroshow, Mayer Fishman, Bonny Johnson, Caroline Clairmont, Dan Sullivan, Mario Sznol. A phase I trial of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone in combination with gemcitabine for patients with advanced cancer.
Cancer chemotherapy and pharmacology.
2004 Oct; 54(4):331-42. doi:
10.1007/s00280-004-0821-2. [PMID: 15148626] - Scott Wadler, Della Makower, Caroline Clairmont, Paula Lambert, Karen Fehn, Mario Sznol. Phase I and pharmacokinetic study of the ribonucleotide reductase inhibitor, 3-aminopyridine-2-carboxaldehyde thiosemicarbazone, administered by 96-hour intravenous continuous infusion.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
2004 May; 22(9):1553-63. doi:
10.1200/jco.2004.07.158. [PMID: 15117978] - Francis J Giles, Paula M Fracasso, Hagop M Kantarjian, Jorge E Cortes, Randy A Brown, Srdan Verstovsek, Yesid Alvarado, Deborah A Thomas, Stefan Faderl, Guillermo Garcia-Manero, Lisa P Wright, Tom Samson, Ann Cahill, Paula Lambert, William Plunkett, Mario Sznol, John F DiPersio, Varsha Gandhi. Phase I and pharmacodynamic study of Triapine, a novel ribonucleotide reductase inhibitor, in patients with advanced leukemia.
Leukemia research.
2003 Dec; 27(12):1077-83. doi:
10.1016/s0145-2126(03)00118-8. [PMID: 12921943] - John Murren, Manuel Modiano, Caroline Clairmont, Paula Lambert, Niramol Savaraj, Terry Doyle, Mario Sznol. Phase I and pharmacokinetic study of triapine, a potent ribonucleotide reductase inhibitor, administered daily for five days in patients with advanced solid tumors.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2003 Sep; 9(11):4092-100. doi:
NULL. [PMID: 14519631] - Lynn Feun, Manuel Modiano, King Lee, John Mao, Angela Marini, Niramol Savaraj, Patricia Plezia, Bijan Almassian, Elizabeth Colacino, Jessica Fischer, Susan MacDonald. Phase I and pharmacokinetic study of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP) using a single intravenous dose schedule.
Cancer chemotherapy and pharmacology.
2002 Sep; 50(3):223-9. doi:
10.1007/s00280-002-0480-0. [PMID: 12203104] - R A Finch, M C Liu, A H Cory, J G Cory, A C Sartorelli. Triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone; 3-AP): an inhibitor of ribonucleotide reductase with antineoplastic activity.
Advances in enzyme regulation.
1999; 39(?):3-12. doi:
10.1016/s0065-2571(98)00017-x. [PMID: 10470363]