neratinib (BioDeep_00000732907)
代谢物信息卡片
Neratinib (HKI-272)
化学式: C30H29ClN6O3 (556.1989554)
中文名称: 来那替尼
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCOC1=C(C=C2C(=C1)N=CC(=C2NC3=CC(=C(C=C3)OCC4=CC=CC=N4)Cl)C#N)NC(=O)C=CCN(C)C
InChI: InChI=1S/C30H29ClN6O3/c1-4-39-28-16-25-23(15-26(28)36-29(38)9-7-13-37(2)3)30(20(17-32)18-34-25)35-21-10-11-27(24(31)14-21)40-19-22-8-5-6-12-33-22/h5-12,14-16,18H,4,13,19H2,1-3H3,(H,34,35)(H,36,38)/b9-7+
描述信息
L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01E - Protein kinase inhibitors > L01EH - Human epidermal growth factor receptor 2 (her2) tyrosine kinase inhibitors
C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C163760 - HER2-targeting Agent
C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor
C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor > C159156 - HER2 Inhibitor
同义名列表
2 个代谢物同义名
数据库引用编号
7 个数据库交叉引用编号
- ChEBI: CHEBI:61397
- KEGGdrug: D08950
- PubChem: 9915743
- DrugBank: DB11828
- ChEMBL: CHEMBL180022
- CAS: 698387-09-6
- CAS: 876310-02-0
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
- Liting Guo, Weiwei Shao, Chenfei Zhou, Hui Yang, Liu Yang, Qu Cai, Junqing Wang, Yan Shi, Lei Huang, Jun Zhang. Neratinib for HER2-positive breast cancer with an overlooked option.
Molecular medicine (Cambridge, Mass.).
2023 10; 29(1):134. doi:
10.1186/s10020-023-00736-0. [PMID: 37803271] - Sabrina Ninck, Vivek Halder, Jan H Krahn, Daniela Beisser, Sarah Resch, Isobel Dodds, René Scholtysik, Jenny Bormann, Leonard Sewald, Mainak D Gupta, Geronimo Heilmann, Deepak D Bhandari, Kyoko Morimoto, Pierre Buscaill, Bettina Hause, Renier A L van der Hoorn, Farnusch Kaschani, Markus Kaiser. Chemoproteomics Reveals the Pan-HER Kinase Inhibitor Neratinib To Target an Arabidopsis Epoxide Hydrolase Related to Phytohormone Signaling.
ACS chemical biology.
2023 Apr; ?(?):. doi:
10.1021/acschembio.2c00322. [PMID: 37115018] - Linzhou Yin, Pengyu Liu, Yue Jin, Zunxi Ning, Yiren Yang, Huiyuan Gao. Ferroptosis-related small-molecule compounds in cancer therapy: Strategies and applications.
European journal of medicinal chemistry.
2022 Dec; 244(?):114861. doi:
10.1016/j.ejmech.2022.114861. [PMID: 36332549] - Majed Alrobaian, Sagar Suman Panda, Obaid Afzal, Imran Kazmi, Manal A Alossaimi, Fahad A Al-Abbasi, Waleed H Almalki, Kriti Soni, Ozair Alam, Md Naushad Alam, Rehan A Rub, Mahfoozur Rahman, Sarwar Beg. Development of a Validated Bioanalytical UPLC-MS/MS Method for Quantification of Neratinib: A Recent Application to Pharmacokinetic Studies in Rat Plasma.
Journal of chromatographic science.
2022 Jul; 60(6):551-558. doi:
10.1093/chromsci/bmab089. [PMID: 34230967] - Paul Dent, Laurence Booth, Andrew Poklepovic, Daniel Von Hoff, Jennifer Martinez, Yong Zhou, John F Hancock. Osimertinib-resistant NSCLC cells activate ERBB2 and YAP/TAZ and are killed by neratinib.
Biochemical pharmacology.
2021 08; 190(?):114642. doi:
10.1016/j.bcp.2021.114642. [PMID: 34077739] - Thidarath Rattanaburee, Tanotnon Tanawattanasuntorn, Tienthong Thongpanchang, Varomyalin Tipmanee, Potchanapond Graidist. Trans-(-)-Kusunokinin: A Potential Anticancer Lignan Compound against HER2 in Breast Cancer Cell Lines?.
Molecules (Basel, Switzerland).
2021 Jul; 26(15):. doi:
10.3390/molecules26154537. [PMID: 34361688] - Tanveer A Wani, Ahmed H Bakheit, Seema Zargar, Zahi Saad Alanazi, Abdulrahman A Al-Majed. Influence of antioxidant flavonoids quercetin and rutin on the in-vitro binding of neratinib to human serum albumin.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
2021 Feb; 246(?):118977. doi:
10.1016/j.saa.2020.118977. [PMID: 33017787] - Paul Dent, Laurence Booth, Andrew Poklepovic, Jennifer Martinez, Daniel Von Hoff, John F Hancock. Neratinib degrades MST4 via autophagy that reduces membrane stiffness and is essential for the inactivation of PI3K, ERK1/2, and YAP/TAZ signaling.
Journal of cellular physiology.
2020 11; 235(11):7889-7899. doi:
10.1002/jcp.29443. [PMID: 31912905] - Xiaoyun Liu, Dan Feng, Mingyue Zheng, Yongmei Cui, Dafang Zhong. Characterization of covalent binding of tyrosine kinase inhibitors to plasma proteins.
Drug metabolism and pharmacokinetics.
2020 Oct; 35(5):456-465. doi:
10.1016/j.dmpk.2020.07.002. [PMID: 32847720] - Yong Joo Park, Hyoung-Tae An, Jong-Sung Park, Ogyi Park, Alexander J Duh, Kwangmeyung Kim, Kyu Hyuck Chung, Kang Choon Lee, Yumin Oh, Seulki Lee. Tyrosine kinase inhibitor neratinib attenuates liver fibrosis by targeting activated hepatic stellate cells.
Scientific reports.
2020 09; 10(1):14756. doi:
10.1038/s41598-020-71688-2. [PMID: 32901093] - Paul Dent, Laurence Booth, Andrew Poklepovic, Daniel Von Hoff, John F Hancock. Enhanced signaling via ERBB3/PI3K plays a compensatory survival role in pancreatic tumor cells exposed to [neratinib + valproate].
Cellular signalling.
2020 04; 68(?):109525. doi:
10.1016/j.cellsig.2020.109525. [PMID: 31911180] - Tanveer A Wani, Ahmed H Bakheit, Seema Zargar, Humaira Rizwana, Abdulrahman A Al-Majed. Evaluation of competitive binding interaction of neratinib and tamoxifen to serum albumin in multidrug therapy.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.
2020 Feb; 227(?):117691. doi:
10.1016/j.saa.2019.117691. [PMID: 31699587] - Jame Abraham, Albert J Montero, Rachel C Jankowitz, Mohamad Adham Salkeni, Jan H Beumer, Brian F Kiesel, Fanny Piette, Laura M Adamson, Rebecca J Nagy, Richard B Lanman, Jeff Sperinde, Weidong Huang, Carmen J Allegra, Ashok Srinivasan, Ying Wang, Katherine L Pogue-Geile, Peter C Lucas, Samuel A Jacobs. Safety and Efficacy of T-DM1 Plus Neratinib in Patients With Metastatic HER2-Positive Breast Cancer: NSABP Foundation Trial FB-10.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology.
2019 10; 37(29):2601-2609. doi:
10.1200/jco.19.00858. [PMID: 31442103] - Gwendolen Lorch, Karthigayini Sivaprakasam, Victoria Zismann, Nieves Perdigones, Tania Contente-Cuomo, Alexandra Nazareno, Salvatore Facista, Shukmei Wong, Kevin Drenner, Winnie S Liang, Joseph M Amann, Sara L Sinicropi-Yao, Michael J Koenig, Krista La Perle, Timothy G Whitsett, Muhammed Murtaza, Jeffrey M Trent, David P Carbone, William P D Hendricks. Identification of Recurrent Activating HER2 Mutations in Primary Canine Pulmonary Adenocarcinoma.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2019 10; 25(19):5866-5877. doi:
10.1158/1078-0432.ccr-19-1145. [PMID: 31431454] - Paul Dent, Laurence Booth, Jane L Roberts, Junchen Liu, Andrew Poklepovic, Alshad S Lalani, David Tuveson, Jennifer Martinez, John F Hancock. Neratinib inhibits Hippo/YAP signaling, reduces mutant K-RAS expression, and kills pancreatic and blood cancer cells.
Oncogene.
2019 07; 38(30):5890-5904. doi:
10.1038/s41388-019-0849-8. [PMID: 31253872] - Hadir M Maher, Nourah Z Alzoman, Shereen M Shehata, Ashwag O Abahussain. Comparative pharmacokinetic profiles of selected irreversible tyrosine kinase inhibitors, neratinib and pelitinib, with apigenin in rat plasma by UPLC-MS/MS.
Journal of pharmaceutical and biomedical analysis.
2017 Apr; 137(?):258-267. doi:
10.1016/j.jpba.2017.01.039. [PMID: 28167419] - Kiana Keyvanjah, Daniel DiPrimeo, Ai Li, Mohammad Obaidi, Dennis Swearingen, Alvin Wong. Pharmacokinetics of neratinib during coadministration with lansoprazole in healthy subjects.
British journal of clinical pharmacology.
2017 03; 83(3):554-561. doi:
10.1111/bcp.13132. [PMID: 27628584] - Brian F Kiesel, Robert A Parise, Alvin Wong, Kiana Keyvanjah, Samuel Jacobs, Jan H Beumer. LC-MS/MS assay for the quantitation of the tyrosine kinase inhibitor neratinib in human plasma.
Journal of pharmaceutical and biomedical analysis.
2017 Feb; 134(?):130-136. doi:
10.1016/j.jpba.2016.11.035. [PMID: 27907855] - Yoshihiro Shibata, Masato Chiba. The role of extrahepatic metabolism in the pharmacokinetics of the targeted covalent inhibitors afatinib, ibrutinib, and neratinib.
Drug metabolism and disposition: the biological fate of chemicals.
2015 Mar; 43(3):375-84. doi:
10.1124/dmd.114.061424. [PMID: 25504185] - Csilla Hegedüs, Krisztina Truta-Feles, Géza Antalffy, György Várady, Katalin Német, Csilla Ozvegy-Laczka, György Kéri, László Orfi, Gergely Szakács, Jeffrey Settleman, András Váradi, Balázs Sarkadi. Interaction of the EGFR inhibitors gefitinib, vandetanib, pelitinib and neratinib with the ABCG2 multidrug transporter: implications for the emergence and reversal of cancer drug resistance.
Biochemical pharmacology.
2012 Aug; 84(3):260-7. doi:
10.1016/j.bcp.2012.04.010. [PMID: 22548830] - Richat Abbas, Bruce A Hug, Cathie Leister, Daryl Sonnichsen. A double-blind, randomized, multiple-dose, parallel-group study to characterize the occurrence of diarrhea following two different dosing regimens of neratinib, an irreversible pan-ErbB receptor tyrosine kinase inhibitor.
Cancer chemotherapy and pharmacology.
2012 Jul; 70(1):191-9. doi:
10.1007/s00280-012-1857-3. [PMID: 22418773] - Richat Abbas, Bruce A Hug, Cathie Leister, Jaime Burns, Daryl Sonnichsen. Pharmacokinetics of oral neratinib during co-administration of ketoconazole in healthy subjects.
British journal of clinical pharmacology.
2011 Apr; 71(4):522-7. doi:
10.1111/j.1365-2125.2010.03845.x. [PMID: 21395644] - Appavu Chandrasekaran, Li Shen, Susan Lockhead, Aram Oganesian, Jianyao Wang, JoAnn Scatina. Reversible covalent binding of neratinib to human serum albumin in vitro.
Drug metabolism letters.
2010 Dec; 4(4):220-7. doi:
10.2174/187231210792928206. [PMID: 20690900] - Bruce Hug, Richat Abbas, Cathie Leister, Jaime Burns, Daryl Sonnichsen. A single-dose, crossover, placebo- and moxifloxacin-controlled study to assess the effects of neratinib (HKI-272) on cardiac repolarization in healthy adult subjects.
Clinical cancer research : an official journal of the American Association for Cancer Research.
2010 Aug; 16(15):4016-23. doi:
10.1158/1078-0432.ccr-10-0280. [PMID: 20647478] - Jianyao Wang, Xiao Xian Li-Chan, Jim Atherton, Lin Deng, Robert Espina, Linning Yu, Peter Horwatt, Steven Ross, Susan Lockhead, Syed Ahmad, Appavu Chandrasekaran, Aram Oganesian, Joann Scatina, Abdul Mutlib, Rasmy Talaat. Characterization of HKI-272 covalent binding to human serum albumin.
Drug metabolism and disposition: the biological fate of chemicals.
2010 Jul; 38(7):1083-93. doi:
10.1124/dmd.110.032292. [PMID: 20400660] - . .
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