Eribulin (BioDeep_00000672650)
代谢物信息卡片
Eribulin
化学式: C40H59NO11 (729.4087904)
中文名称: 艾日布林
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC1CC2CCC3C(=C)CC(O3)CCC45CC6C(O4)C7C(O6)C(O5)C8C(O7)CCC(O8)CC(=O)CC9C(CC(C1=C)O2)OC(C9OC)CC(CN)O
InChI: InChI=1S/C40H59NO11/c1-19-11-24-5-7-28-20(2)12-26(45-28)9-10-40-17-33-36(51-40)37-38(50-33)39(52-40)35-29(49-37)8-6-25(47-35)13-22(42)14-27-31(16-30(46-24)21(19)3)48-32(34(27)44-4)15-23(43)18-41/h19,23-39,43H,2-3,5-18,41H2,1,4H3/t19-,23+,24+,25-,26+,27+,28+,29+,30-,31+,32-,33-,34-,35+,36+,37+,38-,39+,40+/m1/s1
描述信息
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C273 - Antimitotic Agent
L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents
同义名列表
1 个代谢物同义名
数据库引用编号
5 个数据库交叉引用编号
- ChEBI: CHEBI:63587
- PubChem: 11354606
- DrugBank: DB08871
- ChEMBL: CHEMBL1683590
- CAS: 253128-41-5
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
- Mana Azumi, Kazuya Kusama, Mikihiro Yoshie, Saya Nakano, Atsuya Tsuru, Tomoyasu Kato, Kazuhiro Tamura. Involvement of ferroptosis in eribulin-induced cytotoxicity in ovarian clear cell carcinoma.
European journal of pharmacology.
2024 May; 971(?):176544. doi:
10.1016/j.ejphar.2024.176544. [PMID: 38552939] - Matteo Giulietti, Francesco Piva, Monia Cecati, Serena Maggio, Michele Guescini, Tiziana Saladino, Laura Scortichini, Sonia Crocetti, Miriam Caramanti, Nicola Battelli, Emanuela Romagnoli. Effects of Eribulin on the RNA Content of Extracellular Vesicles Released by Metastatic Breast Cancer Cells.
Cells.
2024 Mar; 13(6):. doi:
10.3390/cells13060479. [PMID: 38534323] - Norikazu Masuda, Makiko Ono, Toru Mukohara, Hiroyuki Yasojima, Tatsunori Shimoi, Kokoro Kobayashi, Kenichi Harano, Makiko Mizutani, Maki Tanioka, Shunji Takahashi, Takahiro Kogawa, Takuya Suzuki, Shiori Okumura, Takao Takase, Reiko Nagai, Taro Semba, Zi-Ming Zhao, Min Ren, Kan Yonemori. Phase 1 study of the liposomal formulation of eribulin (E7389-LF): Results from the breast cancer expansion cohort.
European journal of cancer (Oxford, England : 1990).
2022 06; 168(?):108-118. doi:
10.1016/j.ejca.2022.03.004. [PMID: 35500404] - Jun Sato, Toshio Shimizu, Takafumi Koyama, Satoru Iwasa, Akihiko Shimomura, Shunsuke Kondo, Shigehisa Kitano, Kan Yonemori, Yutaka Fujiwara, Kenji Tamura, Takuya Suzuki, Takao Takase, Reiko Nagai, Kohei Yamaguchi, Taro Semba, Zi-Ming Zhao, Min Ren, Noboru Yamamoto. Dose Escalation Data from the Phase 1 Study of the Liposomal Formulation of Eribulin (E7389-LF) in Japanese Patients with Advanced Solid Tumors.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2022 05; 28(9):1783-1791. doi:
10.1158/1078-0432.ccr-21-3518. [PMID: 35180771] - Yuji Mano. A separate assay of released and liposomal encapsulated eribulin in dog plasma by liquid chromatography with tandem mass spectrometry for its application to a pharmacokinetic study.
Journal of separation science.
2022 May; 45(10):1636-1645. doi:
10.1002/jssc.202200048. [PMID: 35235250] - Toshio Shimizu, Yutaka Fujiwara, Kan Yonemori, Takafumi Koyama, Jun Sato, Kenji Tamura, Akihiko Shimomura, Hiroki Ikezawa, Maiko Nomoto, Keiji Furuuchi, Ryo Nakajima, Takuma Miura, Noboru Yamamoto. First-in-Human Phase 1 Study of MORAb-202, an Antibody-Drug Conjugate Comprising Farletuzumab Linked to Eribulin Mesylate, in Patients with Folate Receptor-α-Positive Advanced Solid Tumors.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2021 07; 27(14):3905-3915. doi:
10.1158/1078-0432.ccr-20-4740. [PMID: 33926914] - Ornella Garrone, Andrea Michelotti, Matteo Paccagnella, Filippo Montemurro, Anna Maria Vandone, Andrea Abbona, Elena Geuna, Paola Vanella, Claudia De Angelis, Cristiana Lo Nigro, Antonella Falletta, Nicola Crosetto, Massimo Di Maio, Marco Merlano. Exploratory analysis of circulating cytokines in patients with metastatic breast cancer treated with eribulin: the TRANSERI-GONO (Gruppo Oncologico del Nord Ovest) study.
ESMO open.
2020 10; 5(5):e000876. doi:
10.1136/esmoopen-2020-000876. [PMID: 33051191] - Norifumi Suzuki, Hiroyuki Tanaka, Hirotoshi Murakami, Nobumoto Tomioka, Kenichi Watanabe, Masayuki Endo, Masato Takahashi. Effect of renal function on neutrophil decreases following eribulin administration.
Cancer reports (Hoboken, N.J.).
2020 10; 3(5):e1258. doi:
10.1002/cnr2.1258. [PMID: 33085846] - Andrew J Robles, Raushan T Kurmasheva, Abhik Bandyopadhyay, Doris A Phelps, Stephen W Erickson, Zhao Lai, Dias Kurmashev, Yidong Chen, Malcom A Smith, Peter J Houghton. Evaluation of Eribulin Combined with Irinotecan for Treatment of Pediatric Cancer Xenografts.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2020 06; 26(12):3012-3023. doi:
10.1158/1078-0432.ccr-19-1822. [PMID: 32184294] - Nastassja Tober, Marica Gentile, Giuseppe Iodice. Long-term eribulin treatment in patients with a single kidney and retroperitoneal liposarcoma.
Future oncology (London, England).
2020 Jan; 16(1s):5-8. doi:
10.2217/fon-2019-0595. [PMID: 31872769] - Masamichi Takahashi, Shunichiro Miki, Kenji Fujimoto, Kohei Fukuoka, Yuko Matsushita, Yoshiko Maida, Mami Yasukawa, Mitsuhiro Hayashi, Raku Shinkyo, Kiyomi Kikuchi, Akitake Mukasa, Ryo Nishikawa, Kenji Tamura, Yoshitaka Narita, Akinobu Hamada, Kenkichi Masutomi, Koichi Ichimura. Eribulin penetrates brain tumor tissue and prolongs survival of mice harboring intracerebral glioblastoma xenografts.
Cancer science.
2019 Jul; 110(7):2247-2257. doi:
10.1111/cas.14067. [PMID: 31099446] - T R Jeffry Evans, Emma Dean, L Rhoda Molife, Juanita Lopez, Malcolm Ranson, Fatima El-Khouly, Ishtiaq Zubairi, Claudio Savulsky, Larisa Reyderman, Yan Jia, Lorna Sweeting, Alastair Greystoke, Jorge Barriuso, Rebecca Kristeleit. Phase 1 dose-finding and pharmacokinetic study of eribulin-liposomal formulation in patients with solid tumours.
British journal of cancer.
2019 02; 120(4):379-386. doi:
10.1038/s41416-019-0377-x. [PMID: 30679780] - Natsuko Satomi-Tsushita, Akihiko Shimomura, Juntaro Matsuzaki, Yusuke Yamamoto, Junpei Kawauchi, Satoko Takizawa, Yoshiaki Aoki, Hiromi Sakamoto, Ken Kato, Chikako Shimizu, Takahiro Ochiya, Kenji Tamura. Serum microRNA-based prediction of responsiveness to eribulin in metastatic breast cancer.
PloS one.
2019; 14(9):e0222024. doi:
10.1371/journal.pone.0222024. [PMID: 31483849] - Cindy Pabon, Ashwini K Esnakula, Karen Daily. Tumour lysis syndrome following eribulin for metastatic uterine leiomyosarcoma.
BMJ case reports.
2018 Dec; 11(1):. doi:
10.1136/bcr-2018-224576. [PMID: 30573532] - T Fujimura, Y Sato, Y Kambayashi, K Tanita, A Tsukada, H Terui, A Hashimoto, S Aiba. Three patients with advanced cutaneous angiosarcoma treated with eribulin: investigation of serum soluble CD163 and chemokine (C-X-C motif) ligand 10 as possible biomarkers predicting the biological behaviour of angiosarcoma.
The British journal of dermatology.
2018 12; 179(6):1392-1395. doi:
10.1111/bjd.16676. [PMID: 29663331] - Takahisa Kawamura, Hidefumi Kasai, Valentina Fermanelli, Toshiaki Takahashi, Yukinori Sakata, Toshiyuki Matsuoka, Mika Ishii, Yusuke Tanigawara. Pharmacodynamic analysis of eribulin safety in breast cancer patients using real-world postmarketing surveillance data.
Cancer science.
2018 Sep; 109(9):2822-2829. doi:
10.1111/cas.13708. [PMID: 29933506] - Kota Nakamura, Motoyasu Kato, Yosuke Miyashita, Osamu Nagashima, Shinichi Sasaki, Shigeru Tominaga, Kazuhisa Takahashi. Development of interstitial pneumonia during treatment with eribulin: a case report.
BMC research notes.
2017 Nov; 10(1):557. doi:
10.1186/s13104-017-2882-4. [PMID: 29110735] - Michiko Sugawara, Krista Condon, Earvin Liang, Christopher DesJardins, Edgar Schuck, Kazutomi Kusano, W George Lai. Eribulin shows high concentration and long retention in xenograft tumor tissues.
Cancer chemotherapy and pharmacology.
2017 Aug; 80(2):377-384. doi:
10.1007/s00280-017-3369-7. [PMID: 28664226] - S Stacchiotti, M Saponara, R Frapolli, M Tortoreto, D Cominetti, S Provenzano, T Negri, G P Dagrada, A Gronchi, C Colombo, B Vincenzi, G Badalamenti, V Zuco, S L Renne, P Collini, C Morosi, A P Dei Tos, E Bello, S Pilotti, P G Casali, M D'Incalci, N Zaffaroni. Patient-derived solitary fibrous tumour xenografts predict high sensitivity to doxorubicin/dacarbazine combination confirmed in the clinic and highlight the potential effectiveness of trabectedin or eribulin against this tumour.
European journal of cancer (Oxford, England : 1990).
2017 05; 76(?):84-92. doi:
10.1016/j.ejca.2017.02.002. [PMID: 28284173] - David J Newman. Developing natural product drugs: Supply problems and how they have been overcome.
Pharmacology & therapeutics.
2016 06; 162(?):1-9. doi:
10.1016/j.pharmthera.2015.12.002. [PMID: 26706239] - Krystyna M Wozniak, James J Vornov, Ying Wu, Kenichi Nomoto, Bruce A Littlefield, Christopher DesJardins, Yanke Yu, George Lai, Larisa Reyderman, Nancy Wong, Barbara S Slusher. Sustained Accumulation of Microtubule-Binding Chemotherapy Drugs in the Peripheral Nervous System: Correlations with Time Course and Neurotoxic Severity.
Cancer research.
2016 06; 76(11):3332-9. doi:
10.1158/0008-5472.can-15-2525. [PMID: 27197173] - Shigeto Ueda, Toshiaki Saeki, Hideki Takeuchi, Takashi Shigekawa, Tomohiko Yamane, Ichiei Kuji, Akihiko Osaki. In vivo imaging of eribulin-induced reoxygenation in advanced breast cancer patients: a comparison to bevacizumab.
British journal of cancer.
2016 May; 114(11):1212-8. doi:
10.1038/bjc.2016.122. [PMID: 27140309] - Antoinette R Tan, John Sarantopoulos, Lucy Lee, Larisa Reyderman, Yi He, Martin Olivo, Sanjay Goel. Pharmacokinetics of eribulin mesylate in cancer patients with normal and impaired renal function.
Cancer chemotherapy and pharmacology.
2015 Nov; 76(5):1051-61. doi:
10.1007/s00280-015-2878-5. [PMID: 26433580] - Robert J Morgan, Timothy W Synold, Jeffrey A Longmate, David I Quinn, David Gandara, Heinz-Josef Lenz, Christopher Ruel, Bixin Xi, Michael D Lewis, A Dimitrios Colevas, James Doroshow, Edward M Newman. Pharmacodynamics (PD) and pharmacokinetics (PK) of E7389 (eribulin, halichondrin B analog) during a phase I trial in patients with advanced solid tumors: a California Cancer Consortium trial.
Cancer chemotherapy and pharmacology.
2015 Nov; 76(5):897-907. doi:
10.1007/s00280-015-2868-7. [PMID: 26362045] - Thierry Lesimple, Julien Edeline, Timothy J Carrothers, Frédérique Cvitkovic, Borje Darpo, Jean-Pierre Delord, Hervé Léna, Nicolas Penel, Geoff J Edwards, Kenneth Law, Jantien Wanders, Allan Kristensen, Larisa Reyderman. A phase I, open-label, single-arm study for QT assessment of eribulin mesylate in patients with advanced solid tumors.
Investigational new drugs.
2013 Aug; 31(4):900-9. doi:
10.1007/s10637-012-9893-8. [PMID: 23143778] - L A Devriese, M Mergui-Roelvink, J Wanders, A Jenner, G Edwards, L Reyderman, W Copalu, F Peng, S Marchetti, J H Beijnen, J H M Schellens. Eribulin mesylate pharmacokinetics in patients with solid tumors receiving repeated oral ketoconazole.
Investigational new drugs.
2013 Apr; 31(2):381-9. doi:
10.1007/s10637-012-9829-3. [PMID: 22555773] - Yanke Yu, Christopher Desjardins, Phil Saxton, George Lai, Edgar Schuck, Y Nancy Wong. Characterization of the pharmacokinetics of a liposomal formulation of eribulin mesylate (E7389) in mice.
International journal of pharmaceutics.
2013 Feb; 443(1-2):9-16. doi:
10.1016/j.ijpharm.2013.01.010. [PMID: 23313921] - Lot A Devriese, Petronella Els O Witteveen, Jantien Wanders, Kenneth Law, Geoff Edwards, Larisa Reyderman, William Copalu, Fuping Peng, Serena Marchetti, Jos H Beijnen, Alwin D R Huitema, Emile E Voest, Jan H M Schellens. Pharmacokinetics of eribulin mesylate in patients with solid tumours receiving repeated oral rifampicin.
British journal of clinical pharmacology.
2013 Feb; 75(2):507-15. doi:
10.1111/j.1365-2125.2012.04381.x. [PMID: 22803519] - L A Devriese, P O Witteveen, S Marchetti, M Mergui-Roelvink, L Reyderman, J Wanders, A Jenner, G Edwards, J H Beijnen, E E Voest, J H M Schellens. Pharmacokinetics of eribulin mesylate in patients with solid tumors and hepatic impairment.
Cancer chemotherapy and pharmacology.
2012 Dec; 70(6):823-32. doi:
10.1007/s00280-012-1976-x. [PMID: 23010853] - Anne-Charlotte Dubbelman, Hilde Rosing, Robert S Jansen, Marja Mergui-Roelvink, Alwin D R Huitema, Barbara Koetz, Margarita Lymboura, Larisa Reyderman, Arturo Lopez-Anaya, Jan H M Schellens, Jos H Beijnen. Mass balance study of [¹⁴C]eribulin in patients with advanced solid tumors.
Drug metabolism and disposition: the biological fate of chemicals.
2012 Feb; 40(2):313-21. doi:
10.1124/dmd.111.042762. [PMID: 22041109] - A C Dubbelman, H Rosing, B Thijssen, L Lucas, W Copalu, J Wanders, J H M Schellens, J H Beijnen. Validation of high-performance liquid chromatography-tandem mass spectrometry assays for the quantification of eribulin (E7389) in various biological matrices.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2011 May; 879(15-16):1149-55. doi:
10.1016/j.jchromb.2011.03.021. [PMID: 21458392] - Jan-Shiang Taur, Christopher S DesJardins, Edgar L Schuck, Y Nancy Wong. Interactions between the chemotherapeutic agent eribulin mesylate (E7389) and P-glycoprotein in CF-1 abcb1a-deficient mice and Caco-2 cells.
Xenobiotica; the fate of foreign compounds in biological systems.
2011 Apr; 41(4):320-6. doi:
10.3109/00498254.2010.542256. [PMID: 21162698] - Antoinette R Tan, Eric H Rubin, Diana C Walton, Dale E Shuster, Y Nancy Wong, Fang Fang, Simon Ashworth, Lee S Rosen. Phase I study of eribulin mesylate administered once every 21 days in patients with advanced solid tumors.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2009 Jun; 15(12):4213-9. doi:
10.1158/1078-0432.ccr-09-0360. [PMID: 19509146] - Christopher Desjardins, Phil Saxton, Sharon X Lu, Xiaofang Li, Christopher Rowbottom, Y Nancy Wong. A high-performance liquid chromatography-tandem mass spectrometry method for the clinical combination study of carboplatin and anti-tumor agent eribulin mesylate (E7389) in human plasma.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2008 Nov; 875(2):373-82. doi:
10.1016/j.jchromb.2008.09.013. [PMID: 18835754] - Wanjun Zheng, Boris M Seletsky, Monica H Palme, Paul J Lydon, Lori A Singer, Charles E Chase, Charles A Lemelin, Yongchun Shen, Heather Davis, Lynda Tremblay, Murray J Towle, Kathleen A Salvato, Bruce F Wels, Kimberley K Aalfs, Yoshito Kishi, Bruce A Littlefield, Melvin J Yu. Macrocyclic ketone analogues of halichondrin B.
Bioorganic & medicinal chemistry letters.
2004 Nov; 14(22):5551-4. doi:
10.1016/j.bmcl.2004.08.069. [PMID: 15482922]