N-Desmethyltamoxifen (BioDeep_00001875917)

Main id: BioDeep_00000011254

 


代谢物信息卡片


N-Desmethyltamoxifen

化学式: C25H27NO (357.20925320000003)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 6.58%

分子结构信息

SMILES: CCC(=C(C1=CC=CC=C1)C2=CC=C(C=C2)OCCNC)C3=CC=CC=C3
InChI: InChI=1S/C25H27NO/c1-3-24(20-10-6-4-7-11-20)25(21-12-8-5-9-13-21)22-14-16-23(17-15-22)27-19-18-26-2/h4-17,26H,3,18-19H2,1-2H3/b25-24-

描述信息

C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent

同义名列表

1 个代谢物同义名

N-Desmethyltamoxifen



数据库引用编号

8 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)

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

  • Yung-Yi Cheng, Elise T Tuzo, Jeffrey W Dalley, Tung-Hu Tsai. Dose-dependent effects of Hedyotis diffusa extract on the pharmacokinetics of tamoxifen, 4-hydroxytamoxifen, and N-desmethyltamoxifen. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Jan; 145(?):112466. doi: 10.1016/j.biopha.2021.112466. [PMID: 34839255]
  • Milena Gusella, Felice Pasini, Barbara Corso, Laura Bertolaso, Giovanni De Rosa, Cristina Falci, Yasmina Modena, Carmen Barile, Donatella Da Corte Z, AnnaPaola Fraccon, Silvia Toso, Elisabetta Cretella, Antonella Brunello, Caterina Modonesi, Romana Segati, Cristina Oliani, Nadia Minicuci, Roberto Padrini. Predicting steady-state endoxifen plasma concentrations in breast cancer patients by CYP2D6 genotyping or phenotyping. Which approach is more reliable?. Pharmacology research & perspectives. 2020 10; 8(5):e00646. doi: 10.1002/prp2.646. [PMID: 32813313]
  • João Paulo Bianchi Ximenez, Jurandyr Moreira de Andrade, Maria Paula Marques, Eduardo Barbosa Coelho, Guilherme Suarez-Kurtz, Vera Lucia Lanchote. Hormonal status affects plasma exposure of tamoxifen and its main metabolites in tamoxifen-treated breast cancer patients. BMC pharmacology & toxicology. 2019 12; 20(Suppl 1):81. doi: 10.1186/s40360-019-0358-y. [PMID: 31852530]
  • Janet Chollet, Fred Mermelstein, Stephen C Rocamboli, David R Friend. Vaginal tamoxifen for treatment of vulvar and vaginal atrophy: Pharmacokinetics and local tolerance in a rabbit model over 28 days. International journal of pharmaceutics. 2019 Oct; 570(?):118691. doi: 10.1016/j.ijpharm.2019.118691. [PMID: 31518632]
  • Lesley J Mills, W Matthew Henderson, Saro Jayaraman, Ruth E Gutjahr-Gobell, Gerald E Zaroogian, Doranne Borsay Horowitz, Susan C Laws. Approaches for predicting effects of unintended environmental exposure to an endocrine active pharmaceutical, tamoxifen. Environmental toxicology. 2016 Dec; 31(12):1834-1850. doi: 10.1002/tox.22184. [PMID: 26303313]
  • Alan K Fotoohi, Hazhar Karim, Pierre Lafolie, Anton Pohanka, Jennie Östervall, Thomas Hatschek, Sigurd Vitols. Pronounced Interindividual But Not Intraindividual Variation in Tamoxifen and Metabolite Levels in Plasma During Adjuvant Treatment of Women With Early Breast Cancer. Therapeutic drug monitoring. 2016 Apr; 38(2):239-45. doi: 10.1097/ftd.0000000000000257. [PMID: 26485084]
  • Marina V Antunes, Tatiana Aparecida da Fontoura Timm, Vanessa de Oliveira, Dilana E Staudt, Suziane Raymundo, Gustavo Gössling, Jorge V Biazús, José A Cavalheiro, Daniela D Rosa, Pierre Wallemacq, Vincent Haufroid, Rafael Linden, Gilberto Schwartsmann. Influence of CYP2D6 and CYP3A4 Phenotypes, Drug Interactions, and Vitamin D Status on Tamoxifen Biotransformation. Therapeutic drug monitoring. 2015 Dec; 37(6):733-44. doi: 10.1097/ftd.0000000000000212. [PMID: 25853922]
  • Samy A F Morad, Myles C Cabot. Tamoxifen regulation of sphingolipid metabolism--Therapeutic implications. Biochimica et biophysica acta. 2015 Sep; 1851(9):1134-45. doi: 10.1016/j.bbalip.2015.05.001. [PMID: 25964209]
  • Samy A F Morad, Su-Fern Tan, David J Feith, Mark Kester, David F Claxton, Thomas P Loughran, Brian M Barth, Todd E Fox, Myles C Cabot. Modification of sphingolipid metabolism by tamoxifen and N-desmethyltamoxifen in acute myelogenous leukemia--Impact on enzyme activity and response to cytotoxics. Biochimica et biophysica acta. 2015 Jul; 1851(7):919-28. doi: 10.1016/j.bbalip.2015.03.001. [PMID: 25769964]
  • Marina Venzon Antunes, Suziane Raymundo, Vanessa de Oliveira, Dilana Elisabeth Staudt, Gustavo Gössling, Giovana Piva Peteffi, Jorge Villanova Biazús, José Antônio Cavalheiro, Marie Tre-Hardy, Arnaud Capron, Vincent Haufroid, Pierre Wallemacq, Gilberto Schwartsmann, Rafael Linden. Ultra-high performance liquid chromatography tandem mass spectrometric method for the determination of tamoxifen, N-desmethyltamoxifen, 4-hydroxytamoxifen and endoxifen in dried blood spots--development, validation and clinical application during breast cancer adjuvant therapy. Talanta. 2015 Jan; 132(?):775-84. doi: 10.1016/j.talanta.2014.10.040. [PMID: 25476377]
  • Juan Peris-Vicente, Enrique Ochoa-Aranda, Devasish Bose, Josep Esteve-Romero. Determination of tamoxifen and its main metabolites in plasma samples from breast cancer patients by micellar liquid chromatography. Talanta. 2015 Jan; 131(?):535-40. doi: 10.1016/j.talanta.2014.07.093. [PMID: 25281137]
  • Philipp Y Maximov, Russell E McDaniel, Daphne J Fernandes, Valeriy R Korostyshevskiy, Puspanjali Bhatta, Thomas E Mürdter, David A Flockhart, V Craig Jordan. Simulation with cells in vitro of tamoxifen treatment in premenopausal breast cancer patients with different CYP2D6 genotypes. British journal of pharmacology. 2014 Dec; 171(24):5624-35. doi: 10.1111/bph.12864. [PMID: 25073551]
  • Cécile Arellano, Ben Allal, Anwar Goubaa, Henri Roché, Etienne Chatelut. An UPLC-MS/MS method for separation and accurate quantification of tamoxifen and its metabolites isomers. Journal of pharmaceutical and biomedical analysis. 2014 Nov; 100(?):254-261. doi: 10.1016/j.jpba.2014.07.033. [PMID: 25173109]
  • Alice I Nichols, Shannon Lubaczewski, Yali Liang, Kyle Matschke, Gabriel Braley, Tanya Ramey. Open-label, 2-period sequential drug interaction study to evaluate the effect of a 100-mg dose of desvenlafaxine on the pharmacokinetics of tamoxifen when coadministered in healthy postmenopausal female subjects. International journal of clinical pharmacology and therapeutics. 2014 10; 52(10):830-41. doi: 10.5414/cp201958. [PMID: 25138680]
  • Ernst A Lien, Håvard Søiland, Steinar Lundgren, Turid Aas, Vidar M Steen, Gunnar Mellgren, Jennifer Gjerde. Serum concentrations of tamoxifen and its metabolites increase with age during steady-state treatment. Breast cancer research and treatment. 2013 Sep; 141(2):243-8. doi: 10.1007/s10549-013-2677-9. [PMID: 23996142]
  • Marina Venzon Antunes, Daniela Dornelles Rosa, Tamyris Dos Santos Viana, Huander Andreolla, Tiago Ozelame Fontanive, Rafael Linden. Sensitive HPLC-PDA determination of tamoxifen and its metabolites N-desmethyltamoxifen, 4-hydroxytamoxifen and endoxifen in human plasma. Journal of pharmaceutical and biomedical analysis. 2013 Mar; 76(?):13-20. doi: 10.1016/j.jpba.2012.12.005. [PMID: 23291438]
  • Casey Lynnette Overby, Emily Beth Devine, Peter Tarczy-Hornoch, Ira J Kalet. Deriving rules and assertions from pharmacogenomics knowledge resources in support of patient drug metabolism efficacy predictions. Journal of the American Medical Informatics Association : JAMIA. 2012 Sep; 19(5):840-50. doi: 10.1136/amiajnl-2011-000405. [PMID: 22539082]
  • Marina V Antunes, Rafael Linden, Tamyris V Santos, Pierre Wallemacq, Vincent Haufroid, Jean-François Classen, Huander Andreolla, Nathalia Costa, Tiago O Fontanive, Daniela D Rosa. Endoxifen levels and its association with CYP2D6 genotype and phenotype: evaluation of a southern Brazilian population under tamoxifen pharmacotherapy. Therapeutic drug monitoring. 2012 Aug; 34(4):422-31. doi: 10.1097/ftd.0b013e318260b46e. [PMID: 22777153]
  • 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]
  • T Langenegger, P Wahl, D Schiesser, B Thürlimann. Plasma levels of tamoxifen, N-desmethyl tamoxifen and anastrozole in a patient with metastatic breast cancer and chronic hemodialysis. Breast cancer research and treatment. 2006 Nov; 100(2):177-81. doi: 10.1007/s10549-006-9243-7. [PMID: 16688477]
  • J Gjerde, E R Kisanga, M Hauglid, P I Holm, G Mellgren, E A Lien. Identification and quantification of tamoxifen and four metabolites in serum by liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 2005 Jul; 1082(1):6-14. doi: 10.1016/j.chroma.2005.01.004. [PMID: 16038189]
  • Brooke Ratliff, Eric C Dietze, Gregory R Bean, Cassandra Moore, Sam Wanko, Victoria L Seewaldt. Re: Active tamoxifen metabolite plasma concentrations after coadministration of tamoxifen and the selective serotonin reuptake inhibitor paroxetine. Journal of the National Cancer Institute. 2004 Jun; 96(11):883; author reply 884-5. doi: 10.1093/jnci/djh170. [PMID: 15173275]
  • Lisa Gallicchio, Gwyn Lord, Katherine Tkaczuk, Malcolm Danton, Lynn M Lewis, Chang K Lim, Jodi A Flaws. Association of tamoxifen (TAM) and TAM metabolite concentrations with self-reported side effects of TAM in women with breast cancer. Breast cancer research and treatment. 2004 May; 85(1):89-97. doi: 10.1023/b:brea.0000021050.92539.b0. [PMID: 15039600]
  • Elton R Kisanga, Jennifer Gjerde, Aliana Guerrieri-Gonzaga, Francesca Pigatto, Adriana Pesci-Feltri, Chris Robertson, Davide Serrano, Giuseppe Pelosi, Andrea Decensi, Ernst A Lien. Tamoxifen and metabolite concentrations in serum and breast cancer tissue during three dose regimens in a randomized preoperative trial. Clinical cancer research : an official journal of the American Association for Cancer Research. 2004 Apr; 10(7):2336-43. doi: 10.1158/1078-0432.ccr-03-0538. [PMID: 15073109]
  • Vered Stearns, Michael D Johnson, James M Rae, Alan Morocho, Antonella Novielli, Pankaj Bhargava, Daniel F Hayes, Zeruesenay Desta, David A Flockhart. Active tamoxifen metabolite plasma concentrations after coadministration of tamoxifen and the selective serotonin reuptake inhibitor paroxetine. Journal of the National Cancer Institute. 2003 Dec; 95(23):1758-64. doi: 10.1093/jnci/djg108. [PMID: 14652237]
  • Hetal R Sheth, Gwyn Lord, Katherine Tkaczuk, Malcolm Danton, Lynn M Lewis, Patricia Langenberg, Chang K Lim, Jodi Anne Flaws. Aging may be associated with concentrations of tamoxifen and its metabolites in breast cancer patients. Journal of women's health (2002). 2003 Oct; 12(8):799-808. doi: 10.1089/154099903322447765. [PMID: 14588130]
  • A Guerrieri-Gonzaga, L Baglietto, H Johansson, B Bonanni, C Robertson, M T Sandri, L Canigiula, C Lampreda, S Diani, E A Lien, A Decensi. Correlation between tamoxifen elimination and biomarker recovery in a primary prevention trial. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2001 Sep; 10(9):967-70. doi: NULL. [PMID: 11535549]
  • M K Gill-Sharma, N Balasinor, P Parte, M Aleem, H S Juneja. Effects of tamoxifen metabolites on fertility of male rat. Contraception. 2001 Feb; 63(2):103-9. doi: 10.1016/s0010-7824(01)00178-0. [PMID: 11292475]
  • S Mandlekar, V Hebbar, K Christov, A N Kong. Pharmacodynamics of tamoxifen and its 4-hydroxy and N-desmethyl metabolites: activation of caspases and induction of apoptosis in rat mammary tumors and in human breast cancer cell lines. Cancer research. 2000 Dec; 60(23):6601-6. doi: NULL. [PMID: 11118041]
  • J M Sanders, L T Burka, M D Shelby, R R Newbold, M L Cunningham. Determination of tamoxifen and metabolites in serum by capillary electrophoresis using a nonaqueous buffer system. Journal of chromatography. B, Biomedical sciences and applications. 1997 Jul; 695(1):181-5. doi: 10.1016/s0378-4347(97)00099-6. [PMID: 9271143]
  • A M Davies, E A Martin, R M Jones, C K Lim, L L Smith, I N White. Peroxidase activation of tamoxifen and toremifene resulting in DNA damage and covalently bound protein adducts. Carcinogenesis. 1995 Mar; 16(3):539-45. doi: 10.1093/carcin/16.3.539. [PMID: 7697811]
  • E Berman, M McBride, W Tong. Comparative activity of tamoxifen and N-desmethyltamoxifen in human multidrug resistant leukemia cell lines. Leukemia. 1994 Jul; 8(7):1191-6. doi: . [PMID: 8035611]
  • K M Fried, I W Wainer. Direct determination of tamoxifen and its four major metabolites in plasma using coupled column high-performance liquid chromatography. Journal of chromatography. B, Biomedical applications. 1994 May; 655(2):261-8. doi: 10.1016/0378-4347(94)00054-9. [PMID: 8081472]
  • Y P Dragan, S Fahey, K Street, J Vaughan, V C Jordan, H C Pitot. Studies of tamoxifen as a promoter of hepatocarcinogenesis in female Fischer F344 rats. Breast cancer research and treatment. 1994; 31(1):11-25. doi: 10.1007/bf00689673. [PMID: 7981451]
  • M J Millward, E A Lien, A Robinson, B M Cantwell. High-dose (480 mg/day) tamoxifen with etoposide: a study of a potential multi-drug resistance modulator. Oncology. 1994 Jan; 51(1):79-83. doi: 10.1159/000227315. [PMID: 8265108]
  • S R Johnston, B P Haynes, N P Sacks, J A McKinna, L J Griggs, M Jarman, M Baum, I E Smith, M Dowsett. Effect of oestrogen receptor status and time on the intra-tumoural accumulation of tamoxifen and N-desmethyltamoxifen following short-term therapy in human primary breast cancer. Breast cancer research and treatment. 1993 Dec; 28(3):241-50. doi: 10.1007/bf00666585. [PMID: 8018953]
  • S P Robinson, S M Langan-Fahey, D A Johnson, V C Jordan. Metabolites, pharmacodynamics, and pharmacokinetics of tamoxifen in rats and mice compared to the breast cancer patient. Drug metabolism and disposition: the biological fate of chemicals. 1991 Jan; 19(1):36-43. doi: NULL. [PMID: 1673419]
  • S M Langan-Fahey, D C Tormey, V C Jordan. Tamoxifen metabolites in patients on long-term adjuvant therapy for breast cancer. European journal of cancer (Oxford, England : 1990). 1990; 26(8):883-8. doi: 10.1016/0277-5379(90)90191-u. [PMID: 2145931]
  • M C Etienne, G Milano, J L Fischel, M Frenay, E François, J L Formento, J Gioanni, M Namer. Tamoxifen metabolism: pharmacokinetic and in vitro study. British journal of cancer. 1989 Jul; 60(1):30-5. doi: 10.1038/bjc.1989.214. [PMID: 2803912]
  • C Kikuta, R Schmid. Specific high-performance liquid chromatographic analysis of tamoxifen and its major metabolites by 'on-line' extraction and post-column photochemical reaction. Journal of pharmaceutical and biomedical analysis. 1989; 7(3):329-37. doi: 10.1016/0731-7085(89)80100-1. [PMID: 2488634]
  • P H Slee, D De Vos, D Chapman, D Stevenson. The bioavailability of Tamoplex (tamoxifen). Part 3. A steady-state study in breast cancer patients. Pharmaceutisch weekblad. Scientific edition. 1988 Feb; 10(1):22-5. doi: 10.1007/bf01966431. [PMID: 3353207]
  • P J Guelen, D Stevenson, R J Briggs, D de Vos. The bioavailability of Tamoplex (tamoxifen). Part 2. A single dose cross-over study in healthy male volunteers. Methods and findings in experimental and clinical pharmacology. 1987 Oct; 9(10):685-90. doi: NULL. [PMID: 3441162]
  • C Murphy, T Fotsis, P Pantzar, H Adlercreutz, F Martin. Analysis of tamoxifen and its metabolites in human plasma by gas chromatography-mass spectrometry (GC-MS) using selected ion monitoring (SIM). Journal of steroid biochemistry. 1987 May; 26(5):547-55. doi: 10.1016/0022-4731(87)90006-9. [PMID: 3586671]
  • G Milano, M C Etienne, M Frenay, R Khater, J L Formento, N Renee, J L Moll, M Francoual, M Berto, M Namer. Optimised analysis of tamoxifen and its main metabolites in the plasma and cytosol of mammary tumours. British journal of cancer. 1987 May; 55(5):509-12. doi: 10.1038/bjc.1987.103. [PMID: 3606944]
  • C Benz, D Gandara, B Miller, T Drakes, S Monroe, B Wilbur, M DeGregorio. Chemoendocrine therapy with prolonged estrogen priming in advanced breast cancer: endocrine pharmacokinetics and toxicity. Cancer treatment reports. 1987 Mar; 71(3):283-9. doi: . [PMID: 3493069]
  • M Nieder, H Jaeger. Quantification of tamoxifen and N-desmethyltamoxifen in human plasma by high-performance liquid chromatography, photochemical reaction and fluorescence detection, and its application to biopharmaceutic investigations. Journal of chromatography. 1987 Jan; 413(?):207-17. doi: 10.1016/0378-4347(87)80228-1. [PMID: 3558670]
  • J G McVie, G P Simonetti, D Stevenson, R J Briggs, P J Guelen, D de Vos. The bioavailability of Tamoplex (tamoxifen). Part 1. A pilot study. Methods and findings in experimental and clinical pharmacology. 1986 Aug; 8(8):505-12. doi: NULL. [PMID: 3747644]
  • C A O'Brian, R M Liskamp, D H Solomon, I B Weinstein. Triphenylethylenes: a new class of protein kinase C inhibitors. Journal of the National Cancer Institute. 1986 Jun; 76(6):1243-6. doi: . [PMID: 3458960]
  • K Soininen, T Kleimola, I Elomaa, M Salmo, P Rissanen. The steady-state pharmacokinetics of tamoxifen and its metabolites in breast cancer patients. The Journal of international medical research. 1986; 14(3):162-5. doi: 10.1177/030006058601400309. [PMID: 3522312]
  • C P Daniel, S J Gaskell, R I Nicholson. The measurement of tamoxifen and metabolites in the rat and relationship to the response of DMBA-induced mammary tumours. European journal of cancer & clinical oncology. 1984 Jan; 20(1):137-43. doi: 10.1016/0277-5379(84)90045-2. [PMID: 6420159]
  • V C Jordan, R R Bain, R R Brown, B Gosden, M A Santos. Determination and pharmacology of a new hydroxylated metabolite of tamoxifen observed in patient sera during therapy for advanced breast cancer. Cancer research. 1983 Mar; 43(3):1446-50. doi: NULL. [PMID: 6825112]
  • R R Brown, R Bain, V C Jordan. Determination of tamoxifen and metabolites in human serum by high-performance liquid chromatography with post-column fluorescence activation. Journal of chromatography. 1983 Feb; 272(2):351-8. doi: 10.1016/s0378-4347(00)86138-1. [PMID: 6833432]
  • V C Jordan. Metabolites of tamoxifen in animals and man: identification, pharmacology, and significance. Breast cancer research and treatment. 1982; 2(2):123-38. doi: 10.1007/bf01806449. [PMID: 6184101]
  • P Daniel, S J Gaskell, H Bishop, C Campbell, R I Nicholson. Determination of tamoxifen and biologically active metabolites in human breast tumours and plasma. European journal of cancer & clinical oncology. 1981 Nov; 17(11):1183-9. doi: NULL. [PMID: 7199465]
  • J S Patterson, R S Settatree, H K Adam, J V Kemp. Serum concentrations of tamoxifen and major metabolite during long-term nolvadex therapy, correlated with clinical response. European journal of cancer. 1980; Suppl 1(?):89-92. doi: NULL. [PMID: 7318875]
  • P Wilkinson, G Ribeiro, H Adam, J Patterson. Clinical pharmacology of tamoxifen and N-desmethyltamoxifen in patients with advanced breast cancer. Cancer chemotherapy and pharmacology. 1980; 5(2):109-11. doi: 10.1007/bf00435413. [PMID: 7471314]