3-Hydroxytamoxifen (Droloxifene) (BioDeep_00000009816)

human metabolite Endogenous blood metabolite Volatile Flavor Compounds

代谢物信息卡片

3-[(1E)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol

化学式: C26H29NO2 (387.2198174)
中文名称: 屈洛昔芬
谱图信息: 最多检出来源 Homo sapiens(blood) 98.04%

分子结构信息

SMILES: CCC(=C(C1=CC=C(C=C1)OCCN(C)C)C2=CC(=CC=C2)O)C3=CC=CC=C3
InChI: InChI=1S/C26H29NO2/c1-4-25(20-9-6-5-7-10-20)26(22-11-8-12-23(28)19-22)21-13-15-24(16-14-21)29-18-17-27(2)3/h5-16,19,28H,4,17-18H2,1-3H3/b26-25+

描述信息

3-Hydroxytamoxifen (Droloxifene) is only found in individuals that have used or taken Tamoxifen. 3-Hydroxytamoxifen (Droloxifene) is a metabolite of Tamoxifen. 3-hydroxytamoxifen (droloxifene) belongs to the family of Stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
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
D020011 - Protective Agents > D000975 - Antioxidants
D000970 - Antineoplastic Agents
C1892 - Chemopreventive Agent
Same as: D03911

同义名列表

9 个代谢物同义名

3-[(1E)-1-{4-[2-(dimethylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl]phenol; 3-Hydroxytamoxifen (Droloxifene); 3-Hydroxytamoxifen citrate; Meta-hydroxytamoxifen; Droloxifene citrate; 3-Hydroxytamoxifen; DTXSID20274463; Droloxifene; Droloxifene

数据库引用编号

13 个数据库交叉引用编号

ChEBI: CHEBI:34731
KEGG: C14296
PubChem: 3033767
PubChem: 5377
HMDB: HMDB0013868
Metlin: METLIN69947
ChEMBL: CHEMBL487
chemspider: 2298372
CAS: 82413-20-5
PMhub: MS000023635
PubChem: 17395296
NIKKAJI: J33.138D
KNApSAcK: 34731

分类词条

Stilbenes

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

9606 - Homo sapiens: -

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

Huixiao Hong, William S Branham, Hui Wen Ng, Carrie L Moland, Stacey L Dial, Hong Fang, Roger Perkins, Daniel Sheehan, Weida Tong. Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein. Toxicological sciences : an official journal of the Society of Toxicology. 2015 Feb; 143(2):333-48. doi: 10.1093/toxsci/kfu231. [PMID: 25349334]
Yong Huang, Yu Shen, Ying Feng, Lin Cao, Ying Leng. Anti-implantation effect of droloxifene in rats and its relationship with anti-estrogenic activity. Acta pharmacologica Sinica. 2005 Oct; 26(10):1243-7. doi: 10.1111/j.1745-7254.2005.00191.x. [PMID: 16174441]
Balazs Antus, Shanying Liu, Yousheng Yao, Hequn Zou, Erwei Song, Jens Lutz, Uwe Heemann. Effects of progesterone and selective oestrogen receptor modulators on chronic allograft nephropathy in rats. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2005 Feb; 20(2):329-35. doi: 10.1093/ndt/gfh602. [PMID: 15618244]
Ellen W Seely, K Bridget Brosnihan, Xavier Jeunemaitre, Kyoko Okamura, Gordon H Williams, Norman K Hollenberg, David M Herrington. Effects of conjugated oestrogen and droloxifene on the renin-angiotensin system, blood pressure and renal blood flow in postmenopausal women. Clinical endocrinology. 2004 Mar; 60(3):315-21. doi: 10.1046/j.1365-2265.2004.01980.x. [PMID: 15008996]
B A John, R R Brodie, G A Baldock, A McBurney, L F Chasseaud, P Jank, A Von Nieciecki. Pharmacokinetics and metabolism of the anti-oestrogen droloxifene in female human subjects. Xenobiotica; the fate of foreign compounds in biological systems. 2002 Aug; 32(8):699-713. doi: 10.1080/00498250210143029. [PMID: 12296990]
Matthieu Gutman, Steeve Couillard, Jenny Roy, Fernand Labrie, Bernard Candas, Claude Labrie. Comparison of the effects of EM-652 (SCH57068), tamoxifen, toremifene, droloxifene, idoxifene, GW-5638 and raloxifene on the growth of human ZR-75-1 breast tumors in nude mice. International journal of cancer. 2002 May; 99(2):273-8. doi: 10.1002/ijc.10302. [PMID: 11979444]
D M Herrington, K B Brosnihan, B E Pusser, E W Seely, P M Ridker, N Rifai, D B MacLean. Differential effects of E and droloxifene on C-reactive protein and other markers of inflammation in healthy postmenopausal women. The Journal of clinical endocrinology and metabolism. 2001 Sep; 86(9):4216-22. doi: 10.1210/jcem.86.9.7799. [PMID: 11549652]
Y Leng, Z P Gu, L Cao. Apoptosis induced by droloxifene and C-myc, Bax, Bcl-2 protein expression in corpus luteum of pregnant rats. Acta pharmacologica Sinica. 2001 Apr; 22(4):327-34. doi: . [PMID: 11742585]
E Marqusee, L E Braverman, J E Lawrence, J S Carroll, E W Seely. The effect of droloxifene and estrogen on thyroid function in postmenopausal women. The Journal of clinical endocrinology and metabolism. 2000 Nov; 85(11):4407-10. doi: 10.1210/jcem.85.11.6975. [PMID: 11095487]
D M Herrington, B E Pusser, W A Riley, T Y Thuren, K B Brosnihan, E A Brinton, D B MacLean. Cardiovascular effects of droloxifene, a new selective estrogen receptor modulator, in healthy postmenopausal women. Arteriosclerosis, thrombosis, and vascular biology. 2000 Jun; 20(6):1606-12. doi: 10.1161/01.atv.20.6.1606. [PMID: 10845879]
Q Qu, H Zheng, J Dahllund, A Laine, N Cockcroft, Z Peng, M Koskinen, K Hemminki, L Kangas, K Väänänen, P Härkönen. Selective estrogenic effects of a novel triphenylethylene compound, FC1271a, on bone, cholesterol level, and reproductive tissues in intact and ovariectomized rats. Endocrinology. 2000 Feb; 141(2):809-20. doi: 10.1210/endo.141.2.7342. [PMID: 10650964]
L A Fitzpatrick. Selective estrogen receptor modulators and phytoestrogens: new therapies for the postmenopausal women. Mayo Clinic proceedings. 1999 Jun; 74(6):601-7. doi: 10.4065/74.6.601. [PMID: 10377937]
B W Day, V A Tyurin, Y Y Tyurina, M Liu, J A Facey, G Carta, E R Kisin, R K Dubey, V E Kagan. Peroxidase-catalyzed pro- versus antioxidant effects of 4-hydroxytamoxifen: enzyme specificity and biochemical sequelae. Chemical research in toxicology. 1999 Jan; 12(1):28-37. doi: 10.1021/tx980137r. [PMID: 9894015]
J P O'Donnell, N B Khosla, D K Dalvie. Metabolism of droloxifene in the CD-1 mouse, Fischer-344 rat and cynomolgus monkey. Xenobiotica; the fate of foreign compounds in biological systems. 1998 Feb; 28(2):153-66. doi: 10.1080/004982598239650. [PMID: 9522440]
H Z Ke, H K Chen, H A Simmons, H Qi, D T Crawford, C M Pirie, K L Chidsey-Frink, Y F Ma, W S Jee, D D Thompson. Comparative effects of droloxifene, tamoxifen, and estrogen on bone, serum cholesterol, and uterine histology in the ovariectomized rat model. Bone. 1997 Jan; 20(1):31-9. doi: 10.1016/s8756-3282(96)00313-4. [PMID: 8988345]
J Ziegler. Raloxifene, retinoids, and lavender: 'me too' tamoxifen alternatives under study. Journal of the National Cancer Institute. 1996 Aug; 88(16):1100-2. doi: 10.1093/jnci/88.16.1100. [PMID: 8757185]
S I Helle, G B Anker, M Tally, K Hall, P E Lønning. Influence of droloxifene on plasma levels of insulin-like growth factor (IGF)-I, Pro-IGF-IIE, insulin-like growth factor binding protein (IGFBP)-1 and IGFBP-3 in breast cancer patients. The Journal of steroid biochemistry and molecular biology. 1996 Feb; 57(3-4):167-71. doi: 10.1016/0960-0760(95)00257-x. [PMID: 8645625]
J Dalski, M Görlich. Steroid hormone levels in patients with advanced breast cancer during therapy with droloxifene: a pilot study. Tumori. 1996 Jan; 82(1):45-7. doi: 10.1177/030089169608200109. [PMID: 8623503]
S I Helle, P E Lønning. Insulin-like growth factors in breast cancer. Acta oncologica (Stockholm, Sweden). 1996; 35 Suppl 5(?):19-22. doi: 10.3109/02841869609083963. [PMID: 9142960]
D A Tess, R O Cole, S M Toler. Sensitive method for the quantitation of droloxifene in plasma and serum by high-performance liquid chromatography employing fluorimetric detection. Journal of chromatography. B, Biomedical applications. 1995 Dec; 674(2):253-60. doi: 10.1016/0378-4347(95)00305-3. [PMID: 8788154]
H Z Ke, H K Chen, H Qi, C M Pirie, H A Simmons, Y F Ma, W S Jee, D D Thompson. Effects of droloxifene on prevention of cancellous bone loss and bone turnover in the axial skeleton of aged, ovariectomized rats. Bone. 1995 Nov; 17(5):491-6. doi: 10.1016/8756-3282(95)00346-2. [PMID: 8579962]
J Geisler, D Ekse, S Hösch, P E Lønning. Influence of droloxifene (3-hydroxytamoxifen), 40 mg daily, on plasma gonadotrophins, sex hormone binding globulin and estrogen levels in postmenopausal breast cancer patients. The Journal of steroid biochemistry and molecular biology. 1995 Nov; 55(2):193-5. doi: 10.1016/0960-0760(95)00163-t. [PMID: 7495698]
J Geisler, H Haarstad, S Gundersen, N Raabe, S Kvinnsland, P E Lønning. Influence of treatment with the anti-oestrogen 3-hydroxytamoxifen (droloxifene) on plasma sex hormone levels in postmenopausal patients with breast cancer. The Journal of endocrinology. 1995 Aug; 146(2):359-63. doi: 10.1677/joe.0.1460359. [PMID: 7561649]
H Z Ke, H A Simmons, C M Pirie, D T Crawford, D D Thompson. Droloxifene, a new estrogen antagonist/agonist, prevents bone loss in ovariectomized rats. Endocrinology. 1995 Jun; 136(6):2435-41. doi: 10.1210/endo.136.6.7750465. [PMID: 7750465]
E A Lien, G Anker, P E Lønning, P M Ueland. Determination of droloxifene and two metabolites in serum by high-pressure liquid chromatography. Therapeutic drug monitoring. 1995 Jun; 17(3):259-65. doi: 10.1097/00007691-199506000-00008. [PMID: 7624922]
H Aoyagi. [The diverse effects of hormonal therapeutic agents on the proliferations of human breast cancer cell lines, MCF-7 and its variants]. Nihon Naibunpi Gakkai zasshi. 1995 Jan; 71(1):39-52. doi: 10.1507/endocrine1927.71.1_39. [PMID: 7895864]
G Sydow, V Wunderlich. Effects of tamoxifen, droloxifene and 17 beta-estradiol on Rauscher mouse leukemogenesis. Cancer letters. 1994 Jul; 82(1):89-94. doi: 10.1016/0304-3835(94)90150-3. [PMID: 8033074]
Y Tanaka, M Sekiguchi, T Sawamoto, T Hata, Y Esumi, S Sugai, S Ninomiya. Pharmacokinetics of droloxifene in mice, rats, monkeys, premenopausal and postmenopausal patients. European journal of drug metabolism and pharmacokinetics. 1994 Jan; 19(1):47-58. doi: 10.1007/bf03188823. [PMID: 7957452]
H Wiseman, C Smith, B Halliwell, M Cannon, H R Arnstein, M S Lennard. Droloxifene (3-hydroxytamoxifen) has membrane antioxidant ability: potential relevance to its mechanism of therapeutic action in breast cancer. Cancer letters. 1992 Sep; 66(1):61-8. doi: 10.1016/0304-3835(92)90281-y. [PMID: 1451097]
S Kvinnsland. Droloxifene, a new antiestrogen. Hormonal influences in postmenopausal breast cancer patients. American journal of clinical oncology. 1991; 14 Suppl 2(?):S46-51. doi: 10.1097/00000421-199112002-00010. [PMID: 1962597]
O Abe, K Enomoto, K Fujiwara, M Izuo, Y Iino, T Tominaga, K Hayashi, O Takatani, N Kugai, M Yoshida. [Phase I study of FK 435]. Gan no rinsho. Japan journal of cancer clinics. 1990 Jul; 36(8):903-13. doi: NULL. [PMID: 2195179]
M Dietel, R Löser, P Röhlke, W Jonat, A Niendorf, D Gerding, A Kohr, F Hölzel, H Arps. Effect of continuous vs intermittent application of 3-OH-tamoxifen or tamoxifen on the proliferation of the human breast cancer cell line MCF-7 M1. Journal of cancer research and clinical oncology. 1989; 115(1):36-40. doi: 10.1007/bf00391597. [PMID: 2921271]