[(16Z,18E)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] 2-[methyl-(4-methyl-4-sulfanylpentanoyl)amino]propanoate (BioDeep_00000913996)
代谢物信息卡片
[(16Z,18E)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10,12,14(26),16,18-pentaen-6-yl] 2-[methyl-(4-methyl-4-sulfanylpentanoyl)amino]propanoate
化学式: C38H54ClN3O10S (779.3218254000001)
中文名称:
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC1C2CC(C(C=CC=C(CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)CC(C4(C1O4)C)OC(=O)C(C)N(C)C(=O)CCC(C)(C)S)C)C)OC)(NC(=O)O2)O
InChI: InChI=1S/C38H54ClN3O10S/c1-21-12-11-13-28(49-10)38(47)20-27(50-35(46)40-38)22(2)33-37(6,52-33)29(51-34(45)23(3)41(7)30(43)14-15-36(4,5)53)19-31(44)42(8)25-17-24(16-21)18-26(48-9)32(25)39/h11-13,17-18,22-23,27-29,33,47,53H,14-16,19-20H2,1-10H3,(H,40,46)/b13-11+,21-12-
描述信息
D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators
D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents
同义名列表
相关代谢途径
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代谢反应
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文献列表
- Clemence Pouzin, Leonid Gibiansky, Nathalie Fagniez, Mustapha Chadjaa, Michel Tod, Laurent Nguyen. Integrated multiple analytes and semi-mechanistic population pharmacokinetic model of tusamitamab ravtansine, a DM4 anti-CEACAM5 antibody-drug conjugate.
Journal of pharmacokinetics and pharmacodynamics.
2022 06; 49(3):381-394. doi:
10.1007/s10928-021-09799-0. [PMID: 35166967] - Hai-Na Xie, Yu-Yuan Chen, Guo-Biao Zhu, Hai-Hao Han, Xi-Le Hu, Zhi-Qiang Pan, Yi Zang, Dong-Hao Xie, Xiao-Peng He, Jia Li, Tony D James. Targeted delivery of maytansine to liver cancer cells via galactose-modified supramolecular two-dimensional glycomaterial.
Chemical communications (Cambridge, England).
2022 Apr; 58(32):5029-5032. doi:
10.1039/d1cc06809a. [PMID: 35373789] - Yunlin Fu, Shashank Gorityala, Wenkui Li, David Humphries, Aaron Ledvina, Stephanie Cape, Franck Picard. Sensitive LC-MS/MS quantification of unconjugated maytansinoid DM4 and its metabolite S-methyl-DM4 in human plasma.
Bioanalysis.
2022 Mar; 14(6):357-368. doi:
10.4155/bio-2021-0275. [PMID: 35234045] - Chao Xu, Shaojie Liu, Fa Yang, Keying Zhang, Yu Li, Xiaolong Zhao, Jiayu Zhang, Tong Lu, Shiqi Lu, Yao Jiang, Weijun Qin, Changhong Shi, Rui Zhang, An-Gang Yang, Aizhi Zhao, Donghui Han, Weihong Wen. Antibody-drug conjugates targeting CD248+ myofibroblasts effectively alleviate renal fibrosis in mice.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2022 02; 36(2):e22102. doi:
10.1096/fj.202101441r. [PMID: 34972243] - Li Li, Chanrui Wang, Yijue Wu, Lihou Dong, Fang Chen, Kelly Dong, Haifeng Song. Simple and Rapid LC-MS/MS Methods for Quantifying Catabolites of Antibody-Drug Conjugates with SMCC Linker.
Journal of chromatographic science.
2021 Jun; 59(7):642-649. doi:
10.1093/chromsci/bmaa122. [PMID: 33420505] - Juan Li, Siyu Guo, Qiang Hua, Fengxian Hu. Improved AP-3 production through combined ARTP mutagenesis, fermentation optimization, and subsequent genome shuffling.
Biotechnology letters.
2021 Jun; 43(6):1143-1154. doi:
10.1007/s10529-020-03034-5. [PMID: 33751317] - Pengcheng Xu, Ru Wang, Wenqian Yang, Yanyan Liu, Dongsheng He, Zixuan Ye, Daquan Chen, Yuan Ding, Jiasheng Tu, Yan Shen. A DM1-doped porous gold nanoshell system for NIR accelerated redox-responsive release and triple modal imaging guided photothermal synergistic chemotherapy.
Journal of nanobiotechnology.
2021 Mar; 19(1):77. doi:
10.1186/s12951-021-00824-5. [PMID: 33741008] - Vineesh Indira Chandran, Ann-Sofie Månsson, Magdalena Barbachowska, Myriam Cerezo-Magaña, Björn Nodin, Bharat Joshi, Neelima Koppada, Ola M Saad, Oleg Gluz, Karolin Isaksson, Signe Borgquist, Karin Jirström, Ivan Robert Nabi, Helena Jernström, Mattias Belting. Hypoxia Attenuates Trastuzumab Uptake and Trastuzumab-Emtansine (T-DM1) Cytotoxicity through Redistribution of Phosphorylated Caveolin-1.
Molecular cancer research : MCR.
2020 04; 18(4):644-656. doi:
10.1158/1541-7786.mcr-19-0856. [PMID: 31900313] - Kerry A Whalen, Brian H White, James M Quinn, Kristina Kriksciukaite, Rossitza Alargova, Tsun P Au Yeung, Patrick Bazinet, Adam Brockman, Michelle M DuPont, Haley Oller, James Gifford, Charles-Andre Lemelin, Patrick Lim Soo, Samantha Perino, Benoît Moreau, Gitanjali Sharma, Rajesh Shinde, Beata Sweryda-Krawiec, Mark T Bilodeau, Richard Wooster. Targeting the Somatostatin Receptor 2 with the Miniaturized Drug Conjugate, PEN-221: A Potent and Novel Therapeutic for the Treatment of Small Cell Lung Cancer.
Molecular cancer therapeutics.
2019 11; 18(11):1926-1936. doi:
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Cancer chemotherapy and pharmacology.
2019 08; 84(2):327-336. doi:
10.1007/s00280-019-03879-2. [PMID: 31154523] - Hitomi Sakai, Junji Tsurutani, Tsutomu Iwasa, Yoshifumi Komoike, Kazuko Sakai, Kazuto Nishio, Kazuhiko Nakagawa. HER2 genomic amplification in circulating tumor DNA and estrogen receptor positivity predict primary resistance to trastuzumab emtansine (T-DM1) in patients with HER2-positive metastatic breast cancer.
Breast cancer (Tokyo, Japan).
2018 Sep; 25(5):605-613. doi:
10.1007/s12282-018-0861-9. [PMID: 29700710] - Wen Jin, Lyle Burton, Ian Moore. LC-HRMS quantitation of intact antibody drug conjugate trastuzumab emtansine from rat plasma.
Bioanalysis.
2018 Jun; 10(11):851-862. doi:
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Cancer research.
2018 02; 78(3):758-768. doi:
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The AAPS journal.
2017 11; 19(6):1715-1734. doi:
10.1208/s12248-017-0131-3. [PMID: 28808917] - Noriko Iwamoto, Akihiko Shimomura, Kenji Tamura, Akinobu Hamada, Takashi Shimada. LC-MS bioanalysis of Trastuzumab and released emtansine using nano-surface and molecular-orientation limited (nSMOL) proteolysis and liquid-liquid partition in plasma of Trastuzumab emtansine-treated breast cancer patients.
Journal of pharmaceutical and biomedical analysis.
2017 Oct; 145(?):33-39. doi:
10.1016/j.jpba.2017.06.032. [PMID: 28648785] - Chunze Li, Priya Agarwal, Ekaterina Gibiansky, Jin Yan Jin, Susan Dent, Anthony Gonçalves, Ihsan Nijem, Alexander Strasak, Marie-Laurence Harle-Yge, Nataliya Chernyukhin, Pat LoRusso, Sandhya Girish. A Phase I Pharmacokinetic Study of Trastuzumab Emtansine (T-DM1) in Patients with Human Epidermal Growth Factor Receptor 2-Positive Metastatic Breast Cancer and Normal or Reduced Hepatic Function.
Clinical pharmacokinetics.
2017 09; 56(9):1069-1080. doi:
10.1007/s40262-016-0496-y. [PMID: 27995530] - Kathleen N Moore, Hossein Borghaei, David M O'Malley, Woondong Jeong, Shelly M Seward, Todd M Bauer, Raymond P Perez, Ursula A Matulonis, Kelli L Running, Xiaoyan Zhang, Jose F Ponte, Rodrigo Ruiz-Soto, Michael J Birrer. Phase 1 dose-escalation study of mirvetuximab soravtansine (IMGN853), a folate receptor α-targeting antibody-drug conjugate, in patients with solid tumors.
Cancer.
2017 Aug; 123(16):3080-3087. doi:
10.1002/cncr.30736. [PMID: 28440955] - Ping Zhong, Hao Meng, Jie Qiu, Jian Zhang, Huanli Sun, Ru Cheng, Zhiyuan Zhong. αvβ3 Integrin-targeted reduction-sensitive micellar mertansine prodrug: Superb drug loading, enhanced stability, and effective inhibition of melanoma growth in vivo.
Journal of controlled release : official journal of the Controlled Release Society.
2017 08; 259(?):176-186. doi:
10.1016/j.jconrel.2016.12.011. [PMID: 27986551] - Li-Wei Yap, Jesper Brok, Kathy Pritchard-Jones. Role of CD56 in Normal Kidney Development and Wilms Tumorigenesis.
Fetal and pediatric pathology.
2017 Feb; 36(1):62-75. doi:
10.1080/15513815.2016.1256358. [PMID: 27935326] - Mark A Socinski, Frederic J Kaye, David R Spigel, Fred J Kudrik, Santiago Ponce, Peter M Ellis, Margarita Majem, Paul Lorigan, Leena Gandhi, Martin E Gutierrez, Dale Nepert, Jesus Corral, Luis Paz Ares. Phase 1/2 Study of the CD56-Targeting Antibody-Drug Conjugate Lorvotuzumab Mertansine (IMGN901) in Combination With Carboplatin/Etoposide in Small-Cell Lung Cancer Patients With Extensive-Stage Disease.
Clinical lung cancer.
2017 01; 18(1):68-76.e2. doi:
10.1016/j.cllc.2016.09.002. [PMID: 28341109] - Jose F Ponte, Xiuxia Sun, Nicholas C Yoder, Nathan Fishkin, Rassol Laleau, Jennifer Coccia, Leanne Lanieri, Megan Bogalhas, Lintao Wang, Sharon Wilhelm, Wayne Widdison, Jan Pinkas, Thomas A Keating, Ravi Chari, Hans K Erickson, John M Lambert. Understanding How the Stability of the Thiol-Maleimide Linkage Impacts the Pharmacokinetics of Lysine-Linked Antibody-Maytansinoid Conjugates.
Bioconjugate chemistry.
2016 07; 27(7):1588-98. doi:
10.1021/acs.bioconjchem.6b00117. [PMID: 27174129] - Markus Walles, Bettina Rudolph, Thierry Wolf, Julien Bourgailh, Martina Suetterlin, Thomas Moenius, Gisela Peraus, Olivier Heudi, Walid Elbast, Christian Lanshoeft, Sanela Bilic. New Insights in Tissue Distribution, Metabolism, and Excretion of [3H]-Labeled Antibody Maytansinoid Conjugates in Female Tumor-Bearing Nude Rats.
Drug metabolism and disposition: the biological fate of chemicals.
2016 07; 44(7):897-910. doi:
10.1124/dmd.115.069021. [PMID: 27122302] - Haoheng Yan, Yukinori Endo, Yi Shen, David Rotstein, Milos Dokmanovic, Nishant Mohan, Partha Mukhopadhyay, Bin Gao, Pal Pacher, Wen Jin Wu. Ado-Trastuzumab Emtansine Targets Hepatocytes Via Human Epidermal Growth Factor Receptor 2 to Induce Hepatotoxicity.
Molecular cancer therapeutics.
2016 Mar; 15(3):480-90. doi:
10.1158/1535-7163.mct-15-0580. [PMID: 26712117] - Olivier Heudi, Samuel Barteau, Franck Picard, Olivier Kretz. Quantitative analysis of maytansinoid (DM1) in human serum by on-line solid phase extraction coupled with liquid chromatography tandem mass spectrometry - Method validation and its application to clinical samples.
Journal of pharmaceutical and biomedical analysis.
2016 Feb; 120(?):322-32. doi:
10.1016/j.jpba.2015.12.026. [PMID: 26771131] - Laura Cosmai, Maurizio Gallieni, Camillo Porta. Renal toxicity of anticancer agents targeting HER2 and EGFR.
Journal of nephrology.
2015 Dec; 28(6):647-57. doi:
10.1007/s40620-015-0226-9. [PMID: 26341657] - Rémy Gébleux, Sarah Wulhfard, Giulio Casi, Dario Neri. Antibody Format and Drug Release Rate Determine the Therapeutic Activity of Noninternalizing Antibody-Drug Conjugates.
Molecular cancer therapeutics.
2015 Nov; 14(11):2606-12. doi:
10.1158/1535-7163.mct-15-0480. [PMID: 26294742] - Hirdesh Uppal, Estelle Doudement, Kaushiki Mahapatra, Walter C Darbonne, Daniela Bumbaca, Ben-Quan Shen, Xiaoyan Du, Ola Saad, Kristin Bowles, Steve Olsen, Gail D Lewis Phillips, Dylan Hartley, Mark X Sliwkowski, Sandhya Girish, Donna Dambach, Vanitha Ramakrishnan. Potential mechanisms for thrombocytopenia development with trastuzumab emtansine (T-DM1).
Clinical cancer research : an official journal of the American Association for Cancer Research.
2015 Jan; 21(1):123-33. doi:
10.1158/1078-0432.ccr-14-2093. [PMID: 25370470] - Ben-Quan Shen, Daniela Bumbaca, Qin Yue, Ola Saad, Jay Tibbitts, S Cyrus Khojasteh, Sandhya Girish. Non-Clinical Disposition and Metabolism of DM1, a Component of Trastuzumab Emtansine (T-DM1), in Sprague Dawley Rats.
Drug metabolism letters.
2015; 9(2):119-31. doi:
10.2174/1872312809666150602151922. [PMID: 26031461] - Russ Wada, Hans K Erickson, Gail D Lewis Phillips, Carmela A Provenzano, Douglas D Leipold, Elaine Mai, Holly Johnson, Jay Tibbitts. Mechanistic pharmacokinetic/pharmacodynamic modeling of in vivo tumor uptake, catabolism, and tumor response of trastuzumab maytansinoid conjugates.
Cancer chemotherapy and pharmacology.
2014 Nov; 74(5):969-80. doi:
10.1007/s00280-014-2561-2. [PMID: 25186956] - Thomas H Pillow, Janet Tien, Kathryn L Parsons-Reponte, Sunil Bhakta, Hao Li, Leanna R Staben, Guangmin Li, Josefa Chuh, Aimee Fourie-O'Donohue, Martine Darwish, Victor Yip, Luna Liu, Douglas D Leipold, Dian Su, Elmer Wu, Susan D Spencer, Ben-Quan Shen, Keyang Xu, Katherine R Kozak, Helga Raab, Richard Vandlen, Gail D Lewis Phillips, Richard H Scheller, Paul Polakis, Mark X Sliwkowski, John A Flygare, Jagath R Junutula. Site-specific trastuzumab maytansinoid antibody-drug conjugates with improved therapeutic activity through linker and antibody engineering.
Journal of medicinal chemistry.
2014 Oct; 57(19):7890-9. doi:
10.1021/jm500552c. [PMID: 25191794] - Brendan Bender, Douglas D Leipold, Keyang Xu, Ben-Quan Shen, Jay Tibbitts, Lena E Friberg. A mechanistic pharmacokinetic model elucidating the disposition of trastuzumab emtansine (T-DM1), an antibody-drug conjugate (ADC) for treatment of metastatic breast cancer.
The AAPS journal.
2014 Sep; 16(5):994-1008. doi:
10.1208/s12248-014-9618-3. [PMID: 24917179] - Vincent Ribrag, Jehan Dupuis, Herve Tilly, Franck Morschhauser, Fabrice Laine, Roch Houot, Corinne Haioun, Christiane Copie, Andrea Varga, John Lambert, Laurence Hatteville, Samira Ziti-Ljajic, Anne Caron, Sandrine Payrard, Bertrand Coiffier. A dose-escalation study of SAR3419, an anti-CD19 antibody maytansinoid conjugate, administered by intravenous infusion once weekly in patients with relapsed/refractory B-cell non-Hodgkin lymphoma.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2014 Jan; 20(1):213-20. doi:
10.1158/1078-0432.ccr-13-0580. [PMID: 24132920] - Dan Lu, Amita Joshi, Bei Wang, Steve Olsen, Joo-Hee Yi, Ian E Krop, Howard A Burris, Sandhya Girish. An integrated multiple-analyte pharmacokinetic model to characterize trastuzumab emtansine (T-DM1) clearance pathways and to evaluate reduced pharmacokinetic sampling in patients with HER2-positive metastatic breast cancer.
Clinical pharmacokinetics.
2013 Aug; 52(8):657-72. doi:
10.1007/s40262-013-0060-y. [PMID: 23553425] - Naomi Pode-Shakked, Rachel Shukrun, Michal Mark-Danieli, Peter Tsvetkov, Sarit Bahar, Sara Pri-Chen, Ronald S Goldstein, Eithan Rom-Gross, Yoram Mor, Edward Fridman, Karen Meir, Amos Simon, Marcus Magister, Naftali Kaminski, Victor S Goldmacher, Orit Harari-Steinberg, Benjamin Dekel. The isolation and characterization of renal cancer initiating cells from human Wilms' tumour xenografts unveils new therapeutic targets.
EMBO molecular medicine.
2013 01; 5(1):18-37. doi:
10.1002/emmm.201201516. [PMID: 23239665] - Hans K Erickson, John M Lambert. ADME of antibody-maytansinoid conjugates.
The AAPS journal.
2012 Dec; 14(4):799-805. doi:
10.1208/s12248-012-9386-x. [PMID: 22875610] - John A Davis, Dan A Rock, Larry C Wienkers, Josh T Pearson. In vitro characterization of the drug-drug interaction potential of catabolites of antibody-maytansinoid conjugates.
Drug metabolism and disposition: the biological fate of chemicals.
2012 Oct; 40(10):1927-34. doi:
10.1124/dmd.112.046169. [PMID: 22752008] - P D Garzone, A J Atkinson. In search of physiologically based distribution volume estimates for macromolecules.
Clinical pharmacology and therapeutics.
2012 Oct; 92(4):419-21. doi:
10.1038/clpt.2012.156. [PMID: 22992670] - Ben-Quan Shen, Daniela Bumbaca, Ola Saad, Qin Yue, Cinthia V Pastuskovas, S Cyrus Khojasteh, Jay Tibbitts, Surinder Kaur, Bei Wang, Yu-Waye Chu, Patricia M LoRusso, Sandhya Girish. Catabolic fate and pharmacokinetic characterization of trastuzumab emtansine (T-DM1): an emphasis on preclinical and clinical catabolism.
Current drug metabolism.
2012 Sep; 13(7):901-10. doi:
10.2174/138920012802138598. [PMID: 22475269] - Simona Lapusan, Maria B Vidriales, Xavier Thomas, Stephane de Botton, Anne Vekhoff, Ruoping Tang, Charles Dumontet, Rodica Morariu-Zamfir, John M Lambert, Marie-Laure Ozoux, Philippe Poncelet, Jesus F San Miguel, Ollivier Legrand, Daniel J DeAngelo, Francis J Giles, Jean-Pierre Marie. Phase I studies of AVE9633, an anti-CD33 antibody-maytansinoid conjugate, in adult patients with relapsed/refractory acute myeloid leukemia.
Investigational new drugs.
2012 Jun; 30(3):1121-31. doi:
10.1007/s10637-011-9670-0. [PMID: 21519855] - Hans K Erickson, Gail D Lewis Phillips, Douglas D Leipold, Carmela A Provenzano, Elaine Mai, Holly A Johnson, Bert Gunter, Charlene A Audette, Manish Gupta, Jan Pinkas, Jay Tibbitts. The effect of different linkers on target cell catabolism and pharmacokinetics/pharmacodynamics of trastuzumab maytansinoid conjugates.
Molecular cancer therapeutics.
2012 May; 11(5):1133-42. doi:
10.1158/1535-7163.mct-11-0727. [PMID: 22408268] - Manish Gupta, Patricia M Lorusso, Bei Wang, Joo-Hee Yi, Howard A Burris, Muralidhar Beeram, Shanu Modi, Yu-Waye Chu, Samuel Agresta, Barbara Klencke, Amita Joshi, Sandhya Girish. Clinical implications of pathophysiological and demographic covariates on the population pharmacokinetics of trastuzumab emtansine, a HER2-targeted antibody-drug conjugate, in patients with HER2-positive metastatic breast cancer.
Journal of clinical pharmacology.
2012 May; 52(5):691-703. doi:
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Nature biotechnology.
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Chemical communications (Cambridge, England).
2011 Oct; 47(38):10752-4. doi:
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Bioconjugate chemistry.
2011 Apr; 22(4):717-27. doi:
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Cancer research.
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Cancer research.
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Cancer chemotherapy and pharmacology.
2008 Oct; 62(5):911-9. doi:
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International journal of oncology.
2007 Apr; 30(4):927-35. doi:
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Journal of pharmaceutical sciences.
2005 Apr; 94(4):788-97. doi:
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Journal of mass spectrometry : JMS.
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