4-Hydroxytamoxifen (BioDeep_00000002412)
Secondary id: BioDeep_00001868268
human metabolite Endogenous blood metabolite
代谢物信息卡片
4-[(1Z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol
化学式: C26H29NO2 (387.2198)
中文名称: 4-羟基三苯氧胺(Z异构体), (Z)-4-羟基它莫西芬, 4-羟基三苯氧胺
谱图信息:
最多检出来源 Homo sapiens(blood) 17.23%
分子结构信息
SMILES: CCC(=C(C1=CC=C(C=C1)O)C2=CC=C(C=C2)OCCN(C)C)C3=CC=CC=C3
InChI: InChI=1S/C26H29NO2/c1-4-25(20-8-6-5-7-9-20)26(21-10-14-23(28)15-11-21)22-12-16-24(17-13-22)29-19-18-27(2)3/h5-17,28H,4,18-19H2,1-3H3/b26-25-
描述信息
4-Hydroxytamoxifen (Afimoxifene) is a metabolite of Tamoxifen. Afimoxifene (4-hydroxytamoxifen) is a selective estrogen receptor modulator which is the active metabolite of tamoxifen. Afimoxifene is a transdermal gel formulation and is being developed by Ascend Therapeutics, Inc. under the trademark TamoGel. (Wikipedia)
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D020847 - Estrogen Receptor Modulators
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D004965 - Estrogen Antagonists
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
C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist
D000970 - Antineoplastic Agents
C1892 - Chemopreventive Agent
同义名列表
20 个代谢物同义名
4-[(1Z)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol; 4-(1-(4-(2-(Dimethylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol; 4-Hydroxytamoxifen, (Z)-isomer; 4-Hydroxytamoxifen, (e)-isomer; (E/Z)-4-hydroxy Tamoxifen; trans-4-Hydroxytamoxifen; Tamoxifen metabolite b; 4-Monohydroxytamoxifen; Para-hydroxytamoxifen; 4-OHT hydrotamoxifen; 4-Hydroxy-tamoxifen; 4-Hydroxytamoxifen; 4-hydroxytamoxifen; Hydroxytamoxifen; (Z)-Afimoxifene; 4oh-Tamoxifen; Afimoxifene; Tamogel; 4-OHT; Hydroxytamoxifen
数据库引用编号
20 个数据库交叉引用编号
- ChEBI: CHEBI:44616
- KEGG: C05011
- KEGGdrug: D06551
- PubChem: 449459
- PubChem: 63062
- HMDB: HMDB0060530
- Metlin: METLIN708
- DrugBank: DB04468
- ChEMBL: CHEMBL489
- Wikipedia: Afimoxifene
- chemspider: 395987
- CAS: 65213-48-1
- CAS: 68047-06-3
- CAS: 68392-35-8
- CAS: 1077-29-8
- PMhub: MS000002544
- PubChem: 7494
- PDB-CCD: OHT
- NIKKAJI: J370.403C
- KNApSAcK: 44616
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
2 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(2)
- Tamoxifen Action Pathway:
4-Hydroxytamoxifen + Phosphoadenosine phosphosulfate ⟶ 4-Hydroxytamoxifen sulfate + Adenosine 3',5'-diphosphate - Tamoxifen Metabolism Pathway:
4-Hydroxytamoxifen + Phosphoadenosine phosphosulfate ⟶ 4-Hydroxytamoxifen sulfate + Adenosine 3',5'-diphosphate
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
- Kazuki Nishimoto, Nobuyuki Okahashi, Masaharu Maruyama, Yoshihiro Izumi, Kohta Nakatani, Yuki Ito, Junko Iida, Takeshi Bamba, Fumio Matsuda. Lipidome and metabolome analyses reveal metabolic alterations associated with MCF-7 apoptosis upon 4-hydroxytamoxifen treatment.
Scientific reports.
2023 10; 13(1):18549. doi:
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10.1016/j.jpba.2012.12.005. [PMID: 23291438] - 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:
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International journal of pharmaceutics.
2012 Oct; 436(1-2):574-81. doi:
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Breast cancer research and treatment.
2012 Jun; 133(2):793-8. doi:
10.1007/s10549-012-2000-1. [PMID: 22388692] - Gregory A Ellis, Nicholas A McGrath, Michael J Palte, Ronald T Raines. Ribonuclease-Activated Cancer Prodrug.
ACS medicinal chemistry letters.
2012 Feb; 3(4):268-272. doi:
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Phytotherapy research : PTR.
2012 Feb; 26(2):303-7. doi:
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Die Pharmazie.
2012 Feb; 67(2):124-30. doi:
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Molecular endocrinology (Baltimore, Md.).
2011 Dec; 25(12):2029-40. doi:
10.1210/me.2011-1145. [PMID: 22052998] - Cheng Li, Minhee Kim, HongSeok Choi, JunShik Choi. Effects of baicalein on the pharmacokinetics of tamoxifen and its main metabolite, 4-hydroxytamoxifen, in rats: possible role of cytochrome P450 3A4 and P-glycoprotein inhibition by baicalein.
Archives of pharmacal research.
2011 Nov; 34(11):1965-72. doi:
10.1007/s12272-011-1117-9. [PMID: 22139696] - Pengzhi Dong, Tao Xie, Xiaoye Zhou, Wenquan Hu, Yuanli Chen, Yajun Duan, Xiaoju Li, Jihong Han. Induction of macrophage scavenger receptor type BI expression by tamoxifen and 4-hydroxytamoxifen.
Atherosclerosis.
2011 Oct; 218(2):435-42. doi:
10.1016/j.atherosclerosis.2011.06.048. [PMID: 21820658] - Sheelendra Pratap Singh, Wahajuddin, Mushir M Ali, Kanchan Kohli, Girish Kumar Jain. Liquid chromatography-mass spectrometry method for the quantification of tamoxifen and its metabolite 4-hydroxytamoxifen in rat plasma: application to interaction study with biochanin A (an isoflavone).
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.
2011 Oct; 879(27):2845-51. doi:
10.1016/j.jchromb.2011.07.036. [PMID: 21890435] - P Bourassa, S Dubeau, Ghulam M Maharvi, Abdul H Fauq, T J Thomas, H A Tajmir-Riahi. Locating the binding sites of anticancer tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen on bovine serum albumin.
European journal of medicinal chemistry.
2011 Sep; 46(9):4344-53. doi:
10.1016/j.ejmech.2011.07.005. [PMID: 21777996] - Cheng Li, Sung-Cil Lim, Jin Kim, Jun-Shik Choi. Effects of myricetin, an anticancer compound, on the bioavailability and pharmacokinetics of tamoxifen and its main metabolite, 4-hydroxytamoxifen, in rats.
European journal of drug metabolism and pharmacokinetics.
2011 Sep; 36(3):175-82. doi:
10.1007/s13318-011-0036-y. [PMID: 21442417] - P Bourassa, S Dubeau, Ghulam M Maharvi, Abdul H Fauq, T J Thomas, H A Tajmir-Riahi. Binding of antitumor tamoxifen and its metabolites 4-hydroxytamoxifen and endoxifen to human serum albumin.
Biochimie.
2011 Jul; 93(7):1089-101. doi:
10.1016/j.biochi.2011.03.006. [PMID: 21439346] - Na Li, Weiwei Jiang, Kaifeng Rao, Mei Ma, Zijian Wang, Satyanarayanan Senthik Kumaran. Estrogen-related receptor gamma disruption of source water and drinking water treatment processes extracts.
Journal of environmental sciences (China).
2011; 23(2):301-6. doi:
10.1016/s1001-0742(10)60406-8. [PMID: 21517005] - Minji Kim, Lucy Erin O'Brien, Sang-Ho Kwon, Keith E Mostov. STAT1 is required for redifferentiation during Madin-Darby canine kidney tubulogenesis.
Molecular biology of the cell.
2010 Nov; 21(22):3926-33. doi:
10.1091/mbc.e10-02-0112. [PMID: 20861313] - Emily L Rickert, Sean Oriana, Cori Hartman-Frey, Xinghua Long, Timothy T Webb, Kenneth P Nephew, Ross V Weatherman. Synthesis and characterization of fluorescent 4-hydroxytamoxifen conjugates with unique antiestrogenic properties.
Bioconjugate chemistry.
2010 May; 21(5):903-10. doi:
10.1021/bc900461h. [PMID: 20420372] - Giorgia Urbinati, Davide Audisio, Véronique Marsaud, Vincent Plassat, Silvia Arpicco, Brigitte Sola, Elias Fattal, Jack-Michel Renoir. Therapeutic potential of new 4-hydroxy-tamoxifen-loaded pH-gradient liposomes in a multiple myeloma experimental model.
Pharmaceutical research.
2010 Feb; 27(2):327-39. doi:
10.1007/s11095-009-0023-z. [PMID: 20033476] - Cheul-Seong Kim, Sang-Jun Choi, Chi-Young Park, Cheng Li, Jun-Shik Choi. Effects of silybinin on the pharmacokinetics of tamoxifen and its active metabolite, 4-hydroxytamoxifen in rats.
Anticancer research.
2010 Jan; 30(1):79-85. doi:
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Anti-cancer drugs.
2009 Aug; 20(7):584-8. doi:
10.1097/cad.0b013e32832d6834. [PMID: 19491656] - Yukimasa Takeda, Xiaohui Liu, Miho Sumiyoshi, Ayami Matsushima, Miki Shimohigashi, Yasuyuki Shimohigashi. Placenta expressing the greatest quantity of bisphenol A receptor ERR{gamma} among the human reproductive tissues: Predominant expression of type-1 ERRgamma isoform.
Journal of biochemistry.
2009 Jul; 146(1):113-22. doi:
10.1093/jb/mvp049. [PMID: 19304792] - Marcelo F Montenegro, Lisandra R Pessa, Valéria A Gomes, Zeruesenay Desta, David A Flockhart, Jose E Tanus-Santos. Assessment of vascular effects of tamoxifen and its metabolites on the rat perfused hindquarter vascular bed.
Basic & clinical pharmacology & toxicology.
2009 May; 104(5):400-7. doi:
10.1111/j.1742-7843.2009.00377.x. [PMID: 19413660] - Deo Prakash Pandey, Rosamaria Lappano, Lidia Albanito, Antonio Madeo, Marcello Maggiolini, Didier Picard. Estrogenic GPR30 signalling induces proliferation and migration of breast cancer cells through CTGF.
The EMBO journal.
2009 Mar; 28(5):523-32. doi:
10.1038/emboj.2008.304. [PMID: 19153601] - Sarah A Scott, Paige E Selvy, Jason R Buck, Hyekyung P Cho, Tracy L Criswell, Ashley L Thomas, Michelle D Armstrong, Carlos L Arteaga, Craig W Lindsley, H Alex Brown. Design of isoform-selective phospholipase D inhibitors that modulate cancer cell invasiveness.
Nature chemical biology.
2009 Feb; 5(2):108-17. doi:
10.1038/nchembio.140. [PMID: 19136975] - Jun-Shik Choi, Keon Wook Kang. Enhanced tamoxifen bioavailability after oral administration of tamoxifen in rats pretreated with naringin.
Archives of pharmacal research.
2008 Dec; 31(12):1631-6. doi:
10.1007/s12272-001-2161-7. [PMID: 19099234] - Y Xu, Y Sun, L Yao, L Shi, Y Wu, T Ouyang, J Li, T Wang, Z Fan, T Fan, B Lin, L He, P Li, Y Xie. Association between CYP2D6 *10 genotype and survival of breast cancer patients receiving tamoxifen treatment.
Annals of oncology : official journal of the European Society for Medical Oncology.
2008 Aug; 19(8):1423-1429. doi:
10.1093/annonc/mdn155. [PMID: 18407954] - A Ushmorov, M D Hogarty, X Liu, H Knauss, K M Debatin, C Beltinger. N-myc augments death and attenuates protective effects of Bcl-2 in trophically stressed neuroblastoma cells.
Oncogene.
2008 May; 27(24):3424-34. doi:
10.1038/sj.onc.1211017. [PMID: 18193081] - Sang-Chul Shin, Yong-Ji Piao, Jun-Shik Choi. Effects of morin on the bioavailability of tamoxifen and its main metabolite, 4-hydroxytamoxifen, in rats.
In vivo (Athens, Greece).
2008 May; 22(3):391-5. doi:
NULL. [PMID: 18610753] - Yongji Piao, Sang-Chul Shin, Jun-Shik Choi. Effects of oral kaempferol on the pharmacokinetics of tamoxifen and one of its metabolites, 4-hydroxytamoxifen, after oral administration of tamoxifen to rats.
Biopharmaceutics & drug disposition.
2008 May; 29(4):245-9. doi:
10.1002/bdd.593. [PMID: 18338336] - B Pinto, A Bertoli, C Noccioli, S Garritano, D Reali, L Pistelli. Estradiol-antagonistic activity of phenolic compounds from leguminous plants.
Phytotherapy research : PTR.
2008 Mar; 22(3):362-6. doi:
10.1002/ptr.2327. [PMID: 18167044] - Tohru Kimura, Maya Tomooka, Noriko Yamano, Kazushige Murayama, Shogo Matoba, Hiroki Umehara, Yoshiakira Kanai, Toru Nakano. AKT signaling promotes derivation of embryonic germ cells from primordial germ cells.
Development (Cambridge, England).
2008 Mar; 135(5):869-79. doi:
10.1242/dev.013474. [PMID: 18216173] - Miriam B Buck, Janet K Coller, Thomas E Mürdter, Michel Eichelbaum, Cornelius Knabbe. TGFbeta2 and TbetaRII are valid molecular biomarkers for the antiproliferative effects of tamoxifen and tamoxifen metabolites in breast cancer cells.
Breast cancer research and treatment.
2008 Jan; 107(1):15-24. doi:
10.1007/s10549-007-9526-7. [PMID: 18043895] - J Gjerde, M Hauglid, H Breilid, S Lundgren, J E Varhaug, E R Kisanga, G Mellgren, V M Steen, E A Lien. Effects of CYP2D6 and SULT1A1 genotypes including SULT1A1 gene copy number on tamoxifen metabolism.
Annals of oncology : official journal of the European Society for Medical Oncology.
2008 Jan; 19(1):56-61. doi:
10.1093/annonc/mdm434. [PMID: 17947222] - Robert Mansel, Amit Goyal, Elisabeth Le Nestour, Valérie Masini-Etévé, Katharine O'Connell. A phase II trial of Afimoxifene (4-hydroxytamoxifen gel) for cyclical mastalgia in premenopausal women.
Breast cancer research and treatment.
2007 Dec; 106(3):389-97. doi:
10.1007/s10549-007-9507-x. [PMID: 17351746] - Caroline G Roberts, Ebru Gurisik, Trevor J Biden, Robert L Sutherland, Alison J Butt. Synergistic cytotoxicity between tamoxifen and the plant toxin persin in human breast cancer cells is dependent on Bim expression and mediated by modulation of ceramide metabolism.
Molecular cancer therapeutics.
2007 Oct; 6(10):2777-85. doi:
10.1158/1535-7163.mct-07-0374. [PMID: 17913853] - Kin-Chuen Leung, Jesena Brce, Nathan Doyle, Heather J Lee, Gary M Leong, Klara Sjögren, Ken K Y Ho. Regulation of growth hormone signaling by selective estrogen receptor modulators occurs through suppression of protein tyrosine phosphatases.
Endocrinology.
2007 May; 148(5):2417-23. doi:
10.1210/en.2006-1305. [PMID: 17272397] - Kim Leblanc, Emilie Sexton, Sophie Parent, Geoffroy Bélanger, Marie-Claude Déry, Virginie Boucher, Eric Asselin. Effects of 4-hydroxytamoxifen, raloxifene and ICI 182 780 on survival of uterine cancer cell lines in the presence and absence of exogenous estrogens.
International journal of oncology.
2007 Feb; 30(2):477-87. doi:
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Arthritis and rheumatism.
2007 Jan; 56(1):334-44. doi:
10.1002/art.22328. [PMID: 17195237] - Hua-Jun He, Tie-Nian Zhu, Yi Xie, Jinshui Fan, Sutapa Kole, Satya Saxena, Michel Bernier. Pyrrolidine dithiocarbamate inhibits interleukin-6 signaling through impaired STAT3 activation and association with transcriptional coactivators in hepatocytes.
The Journal of biological chemistry.
2006 Oct; 281(42):31369-79. doi:
10.1074/jbc.m603762200. [PMID: 16926159] - Jane L Limer, Alicia T Parkes, Valerie Speirs. Differential response to phytoestrogens in endocrine sensitive and resistant breast cancer cells in vitro.
International journal of cancer.
2006 Aug; 119(3):515-21. doi:
10.1002/ijc.21863. [PMID: 16506217] - Young Chai Lim, Lang Li, Zeruesenay Desta, Qianqian Zhao, James M Rae, David A Flockhart, Todd C Skaar. Endoxifen, a secondary metabolite of tamoxifen, and 4-OH-tamoxifen induce similar changes in global gene expression patterns in MCF-7 breast cancer cells.
The Journal of pharmacology and experimental therapeutics.
2006 Aug; 318(2):503-12. doi:
10.1124/jpet.105.100511. [PMID: 16690721] - Sang-Chul Shin, Jun-Shik Choi, Xiuguo Li. Enhanced bioavailability of tamoxifen after oral administration of tamoxifen with quercetin in rats.
International journal of pharmaceutics.
2006 Apr; 313(1-2):144-9. doi:
10.1016/j.ijpharm.2006.01.028. [PMID: 16516418] - Bo Zhao, Seiji Maruo, Andrew Cooper, Michael R Chase, Eric Johannsen, Elliott Kieff, Ellen Cahir-McFarland. RNAs induced by Epstein-Barr virus nuclear antigen 2 in lymphoblastoid cell lines.
Proceedings of the National Academy of Sciences of the United States of America.
2006 Feb; 103(6):1900-5. doi:
10.1073/pnas.0510612103. [PMID: 16446431] - Daniel R Croft, Michael F Olson. Conditional regulation of a ROCK-estrogen receptor fusion protein.
Methods in enzymology.
2006; 406(?):541-53. doi:
10.1016/s0076-6879(06)06042-3. [PMID: 16472686] - Clara B S Lau, Tony C Y Ho, Terry W L Chan, Stephen C F Kim. Use of dong quai (Angelica sinensis) to treat peri- or postmenopausal symptoms in women with breast cancer: is it appropriate?.
Menopause (New York, N.Y.).
2005 Nov; 12(6):734-40. doi:
10.1097/01.gme.0000184419.65943.01. [PMID: 16278617] - Elton Richard Kisanga, Gunnar Mellgren, Ernst A Lien. Excretion of hydroxylated metabolites of tamoxifen in human bile and urine.
Anticancer research.
2005 Nov; 25(6C):4487-92. doi:
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Oncogene.
2005 Sep; 24(43):6465-81. doi:
10.1038/sj.onc.1208802. [PMID: 16007182] - Jing Jin, James R Woodgett. Chronic activation of protein kinase Bbeta/Akt2 leads to multinucleation and cell fusion in human epithelial kidney cells: events associated with tumorigenesis.
Oncogene.
2005 Aug; 24(35):5459-70. doi:
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Journal of chromatography. A.
2005 Jul; 1082(1):6-14. doi:
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