Patupilone (BioDeep_00000009131)
代谢物信息卡片
epothilone B
化学式: C27H41NO6S (507.2654446000001)
中文名称: 埃博霉素B
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C1(N=C(SC=1)C)/C=C(/[C@H]1OC(=O)C[C@@H](C(C([C@@H]([C@H]([C@@H](C)CCC[C@@]2(C)O[C@@]2([H])C1)O)C)=O)(C)C)O)\C
InChI: InChI=1S/C27H41NO6S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)33-23(30)13-21(29)26(5,6)25(32)17(3)24(15)31/h11,14-15,17,20-22,24,29,31H,8-10,12-13H2,1-7H3/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1
描述信息
An epithilone that is epithilone D in which the double bond in the macrocyclic ring has been oxidised to the corresponding epoxide (the S,S stereoisomer).
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C273 - Antimitotic Agent
D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators
D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents
同义名列表
4 个代谢物同义名
数据库引用编号
19 个数据库交叉引用编号
- ChEBI: CHEBI:94639
- ChEBI: CHEBI:31550
- KEGG: C12154
- PubChem: 448013
- PubChem: 4456137
- Metlin: METLIN41006
- DrugBank: DB03010
- ChEMBL: CHEMBL94657
- LipidMAPS: LMPK04000041
- KNApSAcK: C00044747
- KNApSAcK: C00045299
- CAS: 152044-54-7
- PMhub: MS000022877
- MetaboLights: MTBLC31550
- PubChem: 14301
- PDB-CCD: EPB
- 3DMET: B04442
- NIKKAJI: J1.358.973I
- KNApSAcK: 31550
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)
4 个相关的物种来源信息
- 7461 - Apis cerana: 10.1371/JOURNAL.PONE.0175573
- 34 - Myxococcus xanthus: 10.1021/NP020120F
- 56 - Sorangium cellulosum:
- 56 - Sorangium cellulosum: 10.1016/S0378-1119(00)00149-9
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
- Zhuowen Liang, Na Zhang, Xuankang Wang, Jiawei Zhang, Kun Li, Tao Lei. Epothilone B inactivation of Sirtuin1 promotes mitochondrial reactive oxygen species to induce dysfunction and ferroptosis of Schwann cells.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences.
2023 Feb; 181(?):106350. doi:
10.1016/j.ejps.2022.106350. [PMID: 36496165] - Junheng Liang, Huimin Wang, Xiaoying Bian, Youming Zhang, Guoping Zhao, Xiaoming Ding. Heterologous redox partners supporting the efficient catalysis of epothilone B biosynthesis by EpoK in Schlegelella brevitalea.
Microbial cell factories.
2020 Sep; 19(1):180. doi:
10.1186/s12934-020-01439-5. [PMID: 32933531] - Qiong-Zhen Zeng, Fan Yang, Chen-Guang Li, Li-Hui Xu, Xian-Hui He, Feng-Yi Mai, Chen-Ying Zeng, Cheng-Cheng Zhang, Qing-Bing Zha, Dong-Yun Ouyang. Paclitaxel Enhances the Innate Immunity by Promoting NLRP3 Inflammasome Activation in Macrophages.
Frontiers in immunology.
2019; 10(?):72. doi:
10.3389/fimmu.2019.00072. [PMID: 30761140] - Mike Becquet, Laurent Laborde, Celine Texier, Dario Sterker, Hans-Peter Gschwind, Ulrike Pfaar, Markus Wartmann, Terry M O'Reilly, Paul M McSheehy. Continuous low-dose infusion of patupilone increases the therapeutic index in mouse and rat tumour models.
Anti-cancer drugs.
2018 08; 29(7):691-701. doi:
10.1097/cad.0000000000000639. [PMID: 29734209] - Sara R Noumeur, Soleiman E Helaly, Rolf Jansen, Marcus Gereke, Theresia E B Stradal, Daoud Harzallah, Marc Stadler. Preussilides A-F, Bicyclic Polyketides from the Endophytic Fungus Preussia similis with Antiproliferative Activity.
Journal of natural products.
2017 05; 80(5):1531-1540. doi:
10.1021/acs.jnatprod.7b00064. [PMID: 28398049] - Colette J Shen, Ashish Sharma, Dinh-Van Vuong, Janine T Erler, Martin Pruschy, Angela Broggini-Tenzer. Ionizing radiation induces tumor cell lysyl oxidase secretion.
BMC cancer.
2014 Jul; 14(?):532. doi:
10.1186/1471-2407-14-532. [PMID: 25052686] - Kevin R Kelly, Markus Zollinger, Frédéric Lozac'h, Eugene Tan, Alain Mita, Felix Waldmeier, Patrick Urban, Suraj Anand, Yanfeng Wang, Piet Swart, Chris Takimoto, Monica Mita. Metabolism of patupilone in patients with advanced solid tumor malignancies.
Investigational new drugs.
2013 Jun; 31(3):605-15. doi:
10.1007/s10637-012-9838-2. [PMID: 22918719] - H-M Lu, M Ye. LC-MS/MS method for determination of epothilone B in rat plasma and its application in pharmacokinetic study.
Arzneimittel-Forschung.
2012 Dec; 62(12):609-13. doi:
10.1055/s-0032-1327695. [PMID: 23093482] - Christoph Oehler, Karl Frei, Elisabeth J Rushing, Paul M J McSheehy, Dirk Weber, Peter R Allegrini, Dorothea Weniger, Urs M Lütolf, Alexander Knuth, Yasuhiro Yonekawa, Krisztina Barath, Angela Broggini-Tenzer, Martin Pruschy, Silvia Hofer. Patupilone (epothilone B) for recurrent glioblastoma: clinical outcome and translational analysis of a single-institution phase I/II trial.
Oncology.
2012; 83(1):1-9. doi:
10.1159/000339152. [PMID: 22688083] - Apostolia-Maria Tsimberidou, Chris H M Takimoto, Stacy Moulder, Cynthia Uehara, Monica Mita, Alain Mita, Patrick Urban, Eugene Tan, Yanfeng Wang, David Vining, Razelle Kurzrock. Effects of patupilone on the pharmacokinetics and pharmacodynamics of warfarin in patients with advanced malignancies: a phase I clinical trial.
Molecular cancer therapeutics.
2011 Jan; 10(1):209-17. doi:
10.1158/1535-7163.mct-10-0774. [PMID: 21220503] - Wilfred D Stein, Hui Huang, Michael Menefee, Maureen Edgerly, Herb Kotz, Andrew Dwyer, James Yang, Susan E Bates. Other paradigms: growth rate constants and tumor burden determined using computed tomography data correlate strongly with the overall survival of patients with renal cell carcinoma.
Cancer journal (Sudbury, Mass.).
2009 Sep; 15(5):441-7. doi:
10.1097/ppo.0b013e3181be1b90. [PMID: 19826366] - Xuan Li, Isabel Barasoain, Ruth Matesanz, J Fernando Díaz, Wei-Shuo Fang. Synthesis and biological activities of high affinity taxane-based fluorescent probes.
Bioorganic & medicinal chemistry letters.
2009 Feb; 19(3):751-4. doi:
10.1016/j.bmcl.2008.12.018. [PMID: 19128972] - S Nilgün Cömezoğlu, Van T Ly, Donglu Zhang, W Griffith Humphreys, Samuel J Bonacorsi, Donald W Everett, Marvin B Cohen, Jinping Gan, Jan H Beumer, Jos H Beijnen, H M Schellens, Graham Lappin. Biotransformation profiling of [(14)C]ixabepilone in human plasma, urine and feces samples using accelerator mass spectrometry (AMS).
Drug metabolism and pharmacokinetics.
2009; 24(6):511-22. doi:
10.2133/dmpk.24.511. [PMID: 20045986] - Terence O'Reilly, Markus Wartmann, Joseph Brueggen, Peter R Allegrini, Andreas Floersheimer, Michel Maira, Paul M J McSheehy. Pharmacokinetic profile of the microtubule stabilizer patupilone in tumor-bearing rodents and comparison of anti-cancer activity with other MTS in vitro and in vivo.
Cancer chemotherapy and pharmacology.
2008 Nov; 62(6):1045-54. doi:
10.1007/s00280-008-0695-9. [PMID: 18301895] - J M G Larkin, S B Kaye. Potential clinical applications of epothilones: a review of phase II studies.
Annals of oncology : official journal of the European Society for Medical Oncology.
2007 Jul; 18 Suppl 5(?):v28-34. doi:
10.1093/annonc/mdm176. [PMID: 17656559] - Kristian Pietras, Michael Stumm, Martine Hubert, Elisabeth Buchdunger, Kristofer Rubin, Carl-Henrik Heldin, Paul McSheehy, Markus Wartmann, Arne Ostman. STI571 enhances the therapeutic index of epothilone B by a tumor-selective increase of drug uptake.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2003 Sep; 9(10 Pt 1):3779-87. doi:
. [PMID: 14506171] - Eugene A Woltering, James M Lewis, P Johnstone Maxwell, Daniel J Frey, Yi-Zarn Wang, John Rothermel, Catherine T Anthony, Douglas A Balster, J Patrick O'Leary, Lynn H Harrison. Development of a novel in vitro human tissue-based angiogenesis assay to evaluate the effect of antiangiogenic drugs.
Annals of surgery.
2003 Jun; 237(6):790-8; discussion 798. doi:
10.1097/01.sla.0000072111.53797.44. [PMID: 12796575] - M D Chappell, S J Stachel, C B Lee, S J Danishefsky. En route to a plant scale synthesis of the promising antitumor agent 12,13-desoxyepothilone B.
Organic letters.
2000 Jun; 2(11):1633-6. doi:
10.1021/ol0059302. [PMID: 10841497] - R J Kowalski, P Giannakakou, E Hamel. Activities of the microtubule-stabilizing agents epothilones A and B with purified tubulin and in cells resistant to paclitaxel (Taxol(R)).
The Journal of biological chemistry.
1997 Jan; 272(4):2534-41. doi:
10.1074/jbc.272.4.2534. [PMID: 8999970]