Toremifene (BioDeep_00000003186)

 

Secondary id: BioDeep_00000406047

human metabolite blood metabolite Chemicals and Drugs


代谢物信息卡片


(2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine

化学式: C26H28ClNO (405.18593080000005)
中文名称: 托瑞米芬
谱图信息: 最多检出来源 Homo sapiens(blood) 28.57%

分子结构信息

SMILES: CN(C)CCOC1=CC=C(C=C1)C(=C(CCCl)C2=CC=CC=C2)C3=CC=CC=C3
InChI: InChI=1S/C26H28ClNO/c1-28(2)19-20-29-24-15-13-23(14-16-24)26(22-11-7-4-8-12-22)25(17-18-27)21-9-5-3-6-10-21/h3-16H,17-20H2,1-2H3/b26-25-

描述信息

Toremifene is only found in individuals that have used or taken this drug. It is a first generation nonsteroidal selective estrogen receptor modulator (SERM) that is structurally related to tamoxifen. Like tamoxifen, it is an estrogen agonist for bone tissue and cholesterol metabolism but is antagonistic on mammary and uterine tissue. [PubChem]Toremifene is a nonsteroidal triphenylethylene derivative. Toremifene binds to estrogen receptors and may exert estrogenic, antiestrogenic, or both activities, depending upon the duration of treatment, animal species, gender, target organ, or endpoint selected. The antitumor effect of toremifene in breast cancer is believed to be mainly due to its antiestrogenic effects, in other words, its ability to compete with estrogen for binding sites in the cancer, blocking the growth-stimulating effects of estrogen in the tumor. Toremifene may also inhibit tumor growth through other mechanisms, such as induction of apoptosis, regulation of oncogene expression, and growth factors.
L - Antineoplastic and immunomodulating agents > L02 - Endocrine therapy > L02B - Hormone antagonists and related agents > L02BA - Anti-estrogens
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D020847 - Estrogen Receptor Modulators
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C1821 - Selective Estrogen Receptor Modulator
C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials
C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist
D050071 - Bone Density Conservation Agents
D000970 - Antineoplastic Agents
C1892 - Chemopreventive Agent
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS

同义名列表

10 个代谢物同义名

(2-{4-[(1Z)-4-chloro-1,2-diphenylbut-1-en-1-yl]phenoxy}ethyl)dimethylamine; 2-[4-(4-chloro-1,2-diphenylbut-1-enyl)phenoxy]-N,N-dimethylethanamine; Toremifene citrate (1:1); Toremifene, (e)-isomer; Citrate, toremifene; Toremifene Citrate; Toremifenum; Toremifene; Toremifeno; Fareston



数据库引用编号

20 个数据库交叉引用编号

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)

1 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

  • Wenxia Wang, Xiao'an Liu. Comparison of effects of tamoxifen and Toremifene on hepatic function and serum lipids in breast cancer patients during adjuvant endocrine therapy. Anti-cancer drugs. 2024 Jan; ?(?):. doi: 10.1097/cad.0000000000001572. [PMID: 38241197]
  • Yuechong Li, Zixi Deng, Yingjiao Wang, Songjie Shen. Lipid changes during endocrine therapy in early-stage breast cancer patients: A real-world study. Lipids in health and disease. 2024 Jan; 23(1):9. doi: 10.1186/s12944-024-02002-6. [PMID: 38191454]
  • Sheng Han, Heng Li, Weixiong Chen, Li Yang, Xiankun Tong, Jianping Zuo, Youhong Hu. Discovery of potent ebola entry inhibitors with (3S,4aS,8aS)-2-(3-amino-2-hydroxypropyl) decahydroisoquinoline-3-carboxamide scaffold. European journal of medicinal chemistry. 2022 Oct; 240(?):114608. doi: 10.1016/j.ejmech.2022.114608. [PMID: 35872393]
  • Weihang Zhou, Yiwei Jiang, Yaqian Xu, Yaohui Wang, Xiaowei Ma, Liheng Zhou, Yanping Lin, Yan Wang, Ziping Wu, Min Li, Wenjin Yin, Jinsong Lu. Comparison of adverse drug reactions between tamoxifen and toremifene in breast cancer patients with different CYP2D6 genotypes: A propensity-score matched cohort study. International journal of cancer. 2022 05; 150(10):1664-1676. doi: 10.1002/ijc.33919. [PMID: 34957551]
  • Dandan Song, Yingying Hu, Biyu Diao, Rongrong Miao, Baodan Zhang, Yangjun Cai, Hanqian Zeng, Yuru Zhang, Xiaoqu Hu. Effects of Tamoxifen vs. Toremifene on fatty liver development and lipid profiles in breast Cancer. BMC cancer. 2021 Jul; 21(1):798. doi: 10.1186/s12885-021-08538-5. [PMID: 34246237]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • William R Martin, Feixiong Cheng. Repurposing of FDA-Approved Toremifene to Treat COVID-19 by Blocking the Spike Glycoprotein and NSP14 of SARS-CoV-2. Journal of proteome research. 2020 11; 19(11):4670-4677. doi: 10.1021/acs.jproteome.0c00397. [PMID: 32907334]
  • Zongbi Yi, Binliang Liu, Xiaoying Sun, Guohua Rong, Wenna Wang, Hui Li, Xiuwen Guan, Lixi Li, Jingtong Zhai, Chunxiao Li, Haili Qian, Fei Ma, Binghe Xu. Safety and efficacy of sirolimus combined with endocrine therapy in patients with advanced hormone receptor-positive breast cancer and the exploration of biomarkers. Breast (Edinburgh, Scotland). 2020 Aug; 52(?):17-22. doi: 10.1016/j.breast.2020.04.004. [PMID: 32335491]
  • Irina N Gaisina, Norton P Peet, Letitia Wong, Adam M Schafer, Han Cheng, Manu Anantpadma, Robert A Davey, Gregory R J Thatcher, Lijun Rong. Discovery and Structural Optimization of 4-(Aminomethyl)benzamides as Potent Entry Inhibitors of Ebola and Marburg Virus Infections. Journal of medicinal chemistry. 2020 07; 63(13):7211-7225. doi: 10.1021/acs.jmedchem.0c00463. [PMID: 32490678]
  • Tao He, Wenhao Yang, Xinyi Zhang, Ping Li, Dandan Yang, Yunhao Wu, Yuan Fan, Mengya Xiang, Qianqian Huang, Jing Chen, Runke Zhou, Qing Lv, Jie Chen. Comparative effectiveness of tamoxifen, toremifene, letrozole, anastrozole, and exemestane on lipid profiles in breast cancer patients: A network meta-analysis. Medicine. 2020 Jan; 99(2):e18550. doi: 10.1097/md.0000000000018550. [PMID: 31914031]
  • Zhi Xu, Shi-Jia Zhao, Yi Liu. 1,2,3-Triazole-containing hybrids as potential anticancer agents: Current developments, action mechanisms and structure-activity relationships. European journal of medicinal chemistry. 2019 Dec; 183(?):111700. doi: 10.1016/j.ejmech.2019.111700. [PMID: 31546197]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Faraz Shaikh, Yuguang Zhao, Luis Alvarez, Maria Iliopoulou, Christopher Lohans, Christopher J Schofield, Sergi Padilla-Parra, Shirley W I Siu, Elizabeth E Fry, Jingshan Ren, David I Stuart. Structure-Based in Silico Screening Identifies a Potent Ebolavirus Inhibitor from a Traditional Chinese Medicine Library. Journal of medicinal chemistry. 2019 03; 62(6):2928-2937. doi: 10.1021/acs.jmedchem.8b01328. [PMID: 30785281]
  • Keisei Anan, Shoshu Mitsuyama, Yasuhiro Yanagita, Morihiko Kimura, Hiroyoshi Doihara, Kansei Komaki, Mikihiro Kusama, Tadashi Ikeda. [Follicle-Stimulating Hormone and Estradiol Levels in Japanese Women Treated with Toremifene and Anastrozole for Two Years - A Retrospective Analysis of Data from a Prospective Randomized Trial]. Gan to kagaku ryoho. Cancer & chemotherapy. 2018 Dec; 45(12):1725-1728. doi: . [PMID: 30587728]
  • J-Pablo Salvador, Ester Vila-Roca, Núria Monfort, Rosa Ventura, M-Pilar Marco. New approach based on immunochemical techniques for monitoring of selective estrogen receptor modulators (SERMs) in human urine. Journal of pharmaceutical and biomedical analysis. 2018 Jul; 156(?):147-152. doi: 10.1016/j.jpba.2018.04.027. [PMID: 29704771]
  • Tadahiko Shien, Hiroyoshi Doihara, Nobuaki Sato, Keisei Anan, Kansei Komaki, Keisuke Miyauchi, Yasuhiro Yanagita, Tomomi Fujisawa, Shoshu Mitsuyama, Chizuko Kanbayashi, Mikihiro Kusama, Morihiko Kimura, Hiromitsu Jinno, Muneaki Sano, Tadashi Ikeda. Serum lipid and bone metabolism effects of Toremifene vs. Letrozole as adjuvant therapy for postmenopausal early breast cancer patients: results of a multicenter open randomized study. Cancer chemotherapy and pharmacology. 2018 02; 81(2):269-275. doi: 10.1007/s00280-017-3491-6. [PMID: 29196963]
  • Yi Zeng, Kai Huang, Weiwei Huang. The effect analysis of CYP2D6 gene polymorphism in the toremifene and tamoxifen treatment in patient with breast cancer. Pakistan journal of pharmaceutical sciences. 2017 May; 30(3(Special)):1095-1098. doi: . [PMID: 28671087]
  • Elizabeth A Nelson, Julie Dyall, Thomas Hoenen, Alyson B Barnes, Huanying Zhou, Janie Y Liang, Julia Michelotti, William H Dewey, Lisa Evans DeWald, Richard S Bennett, Patrick J Morris, Rajarshi Guha, Carleen Klumpp-Thomas, Crystal McKnight, Yu-Chi Chen, Xin Xu, Amy Wang, Emma Hughes, Scott Martin, Craig Thomas, Peter B Jahrling, Lisa E Hensley, Gene G Olinger, Judith M White. The phosphatidylinositol-3-phosphate 5-kinase inhibitor apilimod blocks filoviral entry and infection. PLoS neglected tropical diseases. 2017 04; 11(4):e0005540. doi: 10.1371/journal.pntd.0005540. [PMID: 28403145]
  • Evelien Gerits, Valerie Defraine, Katleen Vandamme, Kaat De Cremer, Katrijn De Brucker, Karin Thevissen, Bruno P A Cammue, Serge Beullens, Maarten Fauvart, Natalie Verstraeten, Jan Michiels. Repurposing Toremifene for Treatment of Oral Bacterial Infections. Antimicrobial agents and chemotherapy. 2017 03; 61(3):. doi: 10.1128/aac.01846-16. [PMID: 27993858]
  • María E Fernández-Suárez, Joan C Escolà-Gil, Oscar Pastor, Alberto Dávalos, Francisco Blanco-Vaca, Miguel A Lasunción, Javier Martínez-Botas, Diego Gómez-Coronado. Clinically used selective estrogen receptor modulators affect different steps of macrophage-specific reverse cholesterol transport. Scientific reports. 2016 09; 6(?):32105. doi: 10.1038/srep32105. [PMID: 27601313]
  • Young-Joo Yang, Kang Mo Kim, Ji Hyun An, Dan Bi Lee, Ju Hyun Shim, Young-Suk Lim, Han Chu Lee, Yung Sang Lee, Jin-Hee Ahn, Kyung Hae Jung, Sung-Bae Kim. Clinical significance of fatty liver disease induced by tamoxifen and toremifene in breast cancer patients. Breast (Edinburgh, Scotland). 2016 Aug; 28(?):67-72. doi: 10.1016/j.breast.2016.04.017. [PMID: 27240168]
  • Tetsuya Fujimura, Satoru Takahashi, Haruki Kume, Tomohiko Urano, Kenichi Takayama, Yuta Yamada, Motofumi Suzuki, Hiroshi Fukuhara, Tohru Nakagawa, Satoshi Inoue, Yukio Homma. Toremifene, a selective estrogen receptor modulator, significantly improved biochemical recurrence in bone metastatic prostate cancer: a randomized controlled phase II a trial. BMC cancer. 2015 Nov; 15(?):836. doi: 10.1186/s12885-015-1871-z. [PMID: 26526623]
  • Miyuki Watanabe, Noriko Watanabe, Sakiko Maruyama, Takashi Kawashiro. Comparative metabolic study between two selective estrogen receptor modulators, toremifene and tamoxifen, in human liver microsomes. Drug metabolism and pharmacokinetics. 2015 Oct; 30(5):325-33. doi: 10.1016/j.dmpk.2015.05.004. [PMID: 26423799]
  • Annabel Braem, Kaat De Cremer, Nicolas Delattin, Katrijn De Brucker, Bram Neirinck, Katleen Vandamme, Johan A Martens, Jan Michiels, Jef Vleugels, Bruno P A Cammue, Karin Thevissen. Novel anti-infective implant substrates: controlled release of antibiofilm compounds from mesoporous silica-containing macroporous titanium. Colloids and surfaces. B, Biointerfaces. 2015 Feb; 126(?):481-8. doi: 10.1016/j.colsurfb.2014.12.054. [PMID: 25601097]
  • Kaat De Cremer, Nicolas Delattin, Katrijn De Brucker, Annelies Peeters, Soña Kucharíková, Evelien Gerits, Natalie Verstraeten, Jan Michiels, Patrick Van Dijck, Bruno P A Cammue, Karin Thevissen. Oral administration of the broad-spectrum antibiofilm compound toremifene inhibits Candida albicans and Staphylococcus aureus biofilm formation in vivo. Antimicrobial agents and chemotherapy. 2014 Dec; 58(12):7606-10. doi: 10.1128/aac.03869-14. [PMID: 25288093]
  • Kenichi Sakurai, Shigeru Fujisaki, Saki Nagashima, Tetsuyo Maeda, Ryouichi Tomita, Shuhei Suzuki, Yukiko Hara, Tomohiro Hirano, Katsuhisa Enomoto, Sadao Amano. [Indoleamine 2,3-dioxygenase activity during toremifene therapy for aromatase inhibitor-resistant metastatic breast cancer]. Gan to kagaku ryoho. Cancer & chemotherapy. 2014 Oct; 41(10):1286-8. doi: . [PMID: 25335719]
  • Morihiko Kimura, Takeshi Tominaga, Izo Kimijima, Yuichi Takatsuka, Shigemitsu Takashima, Yasuo Nomura, Fujio Kasumi, Akihiro Yamaguchi, Norikazu Masuda, Shinzaburo Noguchi, Nobuoki Eshima. Phase III randomized trial of toremifene versus tamoxifen for Japanese postmenopausal patients with early breast cancer. Breast cancer (Tokyo, Japan). 2014 May; 21(3):275-83. doi: 10.1007/s12282-012-0394-6. [PMID: 22968626]
  • Nicolas Delattin, Katrijn De Brucker, Katleen Vandamme, Els Meert, Arnaud Marchand, Patrick Chaltin, Bruno P A Cammue, Karin Thevissen. Repurposing as a means to increase the activity of amphotericin B and caspofungin against Candida albicans biofilms. The Journal of antimicrobial chemotherapy. 2014 Apr; 69(4):1035-44. doi: 10.1093/jac/dkt449. [PMID: 24284780]
  • Charles L Vogel, Mary Ann Johnston, Christi Capers, Deborah Braccia. Toremifene for breast cancer: a review of 20 years of data. Clinical breast cancer. 2014 Feb; 14(1):1-9. doi: 10.1016/j.clbc.2013.10.014. [PMID: 24439786]
  • Yuji Kawamura, Hiroyuki Hayashi, Yasushi Kurata, Kazuyuki Hiratsuka, Kenichi Masumura, Takehiko Nohmi. Evaluation of the genotoxicity of tamoxifen in the liver and kidney of F344 gpt delta transgenic rat in 3-week and 13-week repeated dose studies. Toxicology. 2013 Oct; 312(?):56-62. doi: 10.1016/j.tox.2013.07.014. [PMID: 23907062]
  • Monica Mazzarino, Mariangela Biava, Xavier de la Torre, Ilaria Fiacco, Francesco Botrè. Characterization of the biotransformation pathways of clomiphene, tamoxifen and toremifene as assessed by LC-MS/(MS) following in vitro and excretion studies. Analytical and bioanalytical chemistry. 2013 Jun; 405(16):5467-87. doi: 10.1007/s00216-013-6961-7. [PMID: 23604525]
  • Feng Chi, Rong Wu, Yuecan Zeng, Rui Xing, Yang Liu, Zhaoguo Xu. Effects of toremifene versus tamoxifen on breast cancer patients: a meta-analysis. Breast cancer (Tokyo, Japan). 2013 Apr; 20(2):111-22. doi: 10.1007/s12282-012-0430-6. [PMID: 23266963]
  • Juhyun Kim, Christopher C Coss, Christina M Barrett, Michael L Mohler, Casey E Bohl, Chien-Ming Li, Yali He, Karen A Veverka, James T Dalton. Role and pharmacologic significance of cytochrome P-450 2D6 in oxidative metabolism of toremifene and tamoxifen. International journal of cancer. 2013 Mar; 132(6):1475-85. doi: 10.1002/ijc.27794. [PMID: 22915089]
  • Matthew R Smith, Ronald A Morton, K Gary Barnette, Paul R Sieber, S Bruce Malkowicz, Domingo Rodriguez, Michael L Hancock, Mitchell S Steiner. Toremifene to reduce fracture risk in men receiving androgen deprivation therapy for prostate cancer. The Journal of urology. 2013 Jan; 189(1 Suppl):S45-50. doi: 10.1016/j.juro.2012.11.016. [PMID: 23234631]
  • Luigi Gennari, Daniela Merlotti, Konstantinos Stolakis, Ranuccio Nuti. Pharmacokinetic evaluation of toremifene and its clinical implications for the treatment of osteoporosis. Expert opinion on drug metabolism & toxicology. 2012 Apr; 8(4):505-13. doi: 10.1517/17425255.2012.665873. [PMID: 22356442]
  • Monica Mazzarino, Maria Cristina Braganò, Xavier de la Torre, Francesco Molaioni, Francesco Botrè. Relevance of the selective oestrogen receptor modulators tamoxifen, toremifene and clomiphene in doping field: endogenous steroids urinary profile after multiple oral doses. Steroids. 2011 Nov; 76(12):1400-6. doi: 10.1016/j.steroids.2011.06.005. [PMID: 21745489]
  • Keisei Anan, Shoshu Mitsuyama, Yasuhiro Yanagita, Morihiko Kimura, Hiroyoshi Doihara, Kansei Komaki, Mikihiro Kusama, Tadashi Ikeda. Effects of toremifene and anastrozole on serum lipids and bone metabolism in postmenopausal females with estrogen receptor-positive breast cancer: the results of a 2-year multicenter open randomized study. Breast cancer research and treatment. 2011 Aug; 128(3):775-81. doi: 10.1007/s10549-011-1608-x. [PMID: 21638048]
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