Dihydrodiethylstilbestrol (BioDeep_00000001794)

   

human metabolite blood metabolite


代谢物信息卡片


4-[4-(4-hydroxyphenyl)hexan-3-yl]phenol

化学式: C18H22O2 (270.1619712)
中文名称: 己烷雌酚
谱图信息: 最多检出来源 Mentha canadensis(plant) 4.35%

分子结构信息

SMILES: CCC(C(CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
InChI: InChI=1S/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3

描述信息

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens
D000970 - Antineoplastic Agents

同义名列表

9 个代谢物同义名

4-[4-(4-hydroxyphenyl)hexan-3-yl]phenol; 4,4-(1,2-Diethylethylene)Diphenol; Hexestrol, (r*,r*)-(+-)-isomer; Hexestrol, (R-(r*,r*))-isomer; Hexestrol, (S-(r*,r*))-isomer; Hexestrol, (r*,s*)-isomer; Dihydrodiethylstilbestrol; hexestrol; Exestrol



数据库引用编号

14 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

  • 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]
  • 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]
  • Ovokeroye Akpojevwe Abafe, Pumza M Gatyeni, Tlou Chokwe. Development and validation of a confirmatory method for the determination of stilbene estrogens in ostrich serum. Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 2018 Mar; 35(3):458-466. doi: 10.1080/19440049.2017.1411617. [PMID: 29210606]
  • Mosotho J George, Ljiljana Marjanovic, D Bradley G Williams. Picogram-level quantification of some growth hormones in bovine urine using mixed-solvent bubble-in-drop single drop micro-extraction. Talanta. 2015 Nov; 144(?):445-50. doi: 10.1016/j.talanta.2015.06.070. [PMID: 26452846]
  • Iraida G Syasina, Nikita A Shved. Hexestrol- and nonylphenol-induced differential vitellogenin synthesis in female and male barfin plaice Liopsetta pinnifasciata. Environmental toxicology and pharmacology. 2015 Mar; 39(2):597-605. doi: 10.1016/j.etap.2015.01.014. [PMID: 25682006]
  • Huixiao Hong, William S Branham, Stacey L Dial, Carrie L Moland, Hong Fang, Jie Shen, Roger Perkins, Daniel Sheehan, Weida Tong. Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities. Chemical research in toxicology. 2012 Nov; 25(11):2553-66. doi: 10.1021/tx3003406. [PMID: 23013281]
  • Shuyu Nong, Fuhua Lin, Xiaojia Huang, Dongxing Yuan. Preparation of a stir bar sorptive extraction coating based on molecularly imprinted polymer and its application in the extraction of dienestrol and hexestrol in complicated samples. Se pu = Chinese journal of chromatography. 2012 Nov; 30(11):1133-42. doi: 10.3724/sp.j.1123.2012.08034. [PMID: 23451515]
  • Qisheng Zhong, Yufei Hu, Yuling Hu, Gongke Li. Dynamic liquid-liquid-solid microextraction based on molecularly imprinted polymer filaments on-line coupling to high performance liquid chromatography for direct analysis of estrogens in complex samples. Journal of chromatography. A. 2012 Jun; 1241(?):13-20. doi: 10.1016/j.chroma.2012.04.017. [PMID: 22554413]
  • Karol L Thompson, Kylie Haskins, Barry A Rosenzweig, Sharron Stewart, Jun Zhang, David Peters, Alan Knapton, Rodney Rouse, Daniel Mans, Thomas Colatsky. Comparison of the diagnostic accuracy of di-22:6-bis(monoacylglycerol)phosphate and other urinary phospholipids for drug-induced phospholipidosis or tissue injury in the rat. International journal of toxicology. 2012 Jan; 31(1):14-24. doi: 10.1177/1091581811430167. [PMID: 22267869]
  • George Kaklamanos, Georgios Theodoridis, Themistoklis Dabalis. Determination of anabolic steroids in bovine urine by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Aug; 877(23):2330-6. doi: 10.1016/j.jchromb.2009.03.033. [PMID: 19375394]
  • Zhao-Xia Wu, Xiao-Hua Wang, Hong-Zhu Deng. [Effects of Yi Fu Ning soft gelatin capsules on reproductive endocrine-immune function of ovariectomized rats]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2009 Jul; 32(7):1083-6. doi: NULL. [PMID: 19873736]
  • Kathrin Schmidt, Carolin Stachel, Petra Gowik. Development and in-house validation of an LC-MS/MS method for the determination of stilbenes and resorcylic acid lactones in bovine urine. Analytical and bioanalytical chemistry. 2008 Jun; 391(4):1199-210. doi: 10.1007/s00216-008-1943-x. [PMID: 18363048]
  • Elisabete Silva, Martin Scholze, Andreas Kortenkamp. Activity of xenoestrogens at nanomolar concentrations in the E-Screen assay. Environmental health perspectives. 2007 Dec; 115 Suppl 1(?):91-7. doi: 10.1289/ehp.9363. [PMID: 18174956]
  • Toshinobu Tokumoto, Mika Tokumoto, Peter Thomas. Interactions of diethylstilbestrol (DES) and DES analogs with membrane progestin receptor-alpha and the correlation with their nongenomic progestin activities. Endocrinology. 2007 Jul; 148(7):3459-67. doi: 10.1210/en.2006-1694. [PMID: 17446184]
  • Antoni Rúbies, Albert Cabrera, Francesc Centrich. Determination of synthetic hormones in animal urine by high-performance liquid chromatography/mass spectrometry. Journal of AOAC International. 2007 Mar; 90(2):626-32. doi: 10.1093/jaoac/90.2.626. [PMID: 17474533]
  • Mireia Urpi-Sarda, Raul Zamora-Ros, Rosa Lamuela-Raventos, Antonio Cherubini, Olga Jauregui, Rafael de la Torre, Maria Isabel Covas, Ramon Estruch, Walter Jaeger, Cristina Andres-Lacueva. HPLC-tandem mass spectrometric method to characterize resveratrol metabolism in humans. Clinical chemistry. 2007 Feb; 53(2):292-9. doi: 10.1373/clinchem.2006.071936. [PMID: 17170057]
  • Ercole Cavalieri, Eleanor Rogan. Catechol quinones of estrogens in the initiation of breast, prostate, and other human cancers: keynote lecture. Annals of the New York Academy of Sciences. 2006 Nov; 1089(?):286-301. doi: 10.1196/annals.1386.042. [PMID: 17261777]
  • Titus Alfred Makudali Msagati, Mathew Muzi Nindi. The use of liquid membranes in the multi-residue extraction of stilbenes in a variety of biological matrices and their detection with LC-ES-MS. Annali di chimica. 2006 Nov; 96(11-12):635-46. doi: 10.1002/adic.200690066. [PMID: 17217168]
  • ChuanLai Xu, ChiFang Peng, Liqiang Liu, Liying Wang, ZhengYu Jin, XiaoGang Chu. Determination of hexoestrol residues in animal tissues based on enzyme-linked immunosorbent assay and comparison with liquid chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2006 Jun; 41(3):1029-36. doi: 10.1016/j.jpba.2006.01.016. [PMID: 16497468]
  • Shuhei Ishikura, Kengo Matsumoto, Masaharu Sanai, Kenji Horie, Toshiyuki Matsunaga, Kazuo Tajima, Ossama El-Kabbani, Akira Hara. Molecular cloning of a novel type of rat cytoplasmic 17beta-hydroxysteroid dehydrogenase distinct from the type 5 isozyme. Journal of biochemistry. 2006 Jun; 139(6):1053-63. doi: 10.1093/jb/mvj109. [PMID: 16788056]
  • Muhammad Saeed, Sandra J Gunselman, Sheila Higginbotham, Eleanor Rogan, Ercole Cavalieri. Formation of the depurinating N3adenine and N7guanine adducts by reaction of DNA with hexestrol-3',4'-quinone or enzyme-activated 3'-hydroxyhexestrol. Implications for a unifying mechanism of tumor initiation by natural and synthetic estrogens. Steroids. 2005 Jan; 70(1):37-45. doi: 10.1016/j.steroids.2004.09.012. [PMID: 15610895]
  • Leslie C Dickson, James D MacNeil, JoAnn Reid, Adrian C E Fesser. Validation of screening method for residues of diethylstilbestrol, dienestrol, hexestrol, and zeranol in bovine urine using immunoaffinity chromatography and gas chromatography/mass spectrometry. Journal of AOAC International. 2003 Jul; 86(4):631-9. doi: . [PMID: 14509418]
  • R Todd Stravitz, Arun J Sanyal. Drug-induced steatohepatitis. Clinics in liver disease. 2003 May; 7(2):435-51. doi: 10.1016/s1089-3261(03)00027-8. [PMID: 12879993]
  • Yuliya Dobrydneva, Roy L Williams, John A Katzenellenbogen, Paul H Ratz, Peter F Blackmore. Diethylstilbestrol and tetrahydrochrysenes are calcium channel blockers in human platelets: relationship to the stilbene pharmacophore. Thrombosis research. 2003 Apr; 110(1):23-31. doi: 10.1016/s0049-3848(03)00110-5. [PMID: 12877905]
  • Ercole L Cavalieri, Eeanor G Rogan. A unified mechanism in the initiation of cancer. Annals of the New York Academy of Sciences. 2002 Apr; 959(?):341-54. doi: 10.1111/j.1749-6632.2002.tb02105.x. [PMID: 11976208]
  • A Berson, V De Beco, P Lettéron, M A Robin, C Moreau, J El Kahwaji, N Verthier, G Feldmann, B Fromenty, D Pessayre. Steatohepatitis-inducing drugs cause mitochondrial dysfunction and lipid peroxidation in rat hepatocytes. Gastroenterology. 1998 Apr; 114(4):764-74. doi: 10.1016/s0016-5085(98)70590-6. [PMID: 9516397]
  • G G Kuiper, B Carlsson, K Grandien, E Enmark, J Häggblad, S Nilsson, J A Gustafsson. Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology. 1997 Mar; 138(3):863-70. doi: 10.1210/endo.138.3.4979. [PMID: 9048584]
  • A G Reznikov, S V Varga, L V Chaikovskaya, L V Tarasenko, L I Polyakova. Endocrine mechanisms of suppressive effect of low dose estrogen-antiandrogen treatment on androgen-dependent organs of male rats. Journal of endocrinological investigation. 1996 Nov; 19(10):654-8. doi: 10.1007/bf03349034. [PMID: 9007695]
  • F van Bambeke, M P Mingeot-Leclercq, R Brasseur, P M Tulkens, A Schanck. Aminoglycoside antibiotics prevent the formation of non-bilayer structures in negatively-charged membranes. Comparative studies using fusogenic (bis(beta-diethylaminoethylether)hexestrol) and aggregating (spermine) agents. Chemistry and physics of lipids. 1996 Mar; 79(2):123-35. doi: 10.1016/0009-3084(95)02520-0. [PMID: 8640900]
  • H Wiseman, B Halliwell. Carcinogenic antioxidants. Diethylstilboestrol, hexoestrol and 17 alpha-ethynyloestradiol. FEBS letters. 1993 Oct; 332(1-2):159-63. doi: 10.1016/0014-5793(93)80504-n. [PMID: 8405434]
  • H Ohishi, M Ogawa. Structure-activity relationship of 3,3'-dihydroxy-alpha,beta-diethyldiphenylethane and its related compounds. Chemical & pharmaceutical bulletin. 1993 Jun; 41(6):1157-9. doi: 10.1248/cpb.41.1157. [PMID: 8396501]
  • F Martinez-Azorin, J A Teruel, F Fernandez-Belda, J C Gomez-Fernandez. Effect of diethylstilbestrol and related compounds on the Ca(2+)-transporting ATPase of sarcoplasmic reticulum. The Journal of biological chemistry. 1992 Jun; 267(17):11923-9. doi: . [PMID: 1318306]
  • L L Ignatenko, G D Mataradze, A F Buniatian, V B Rozen. [Sex differences in the accumulation of estrogen receptors in nuclei of liver cells and increase of angiotensinogen concentration in the blood of rats after administration of low doses of synthetic estrogens]. Biulleten' eksperimental'noi biologii i meditsiny. 1990 Dec; 110(12):594-6. doi: . [PMID: 1964609]
  • R Bagnati, M G Castelli, L Airoldi, M Paleologo Oriundi, A Ubaldi, R Fanelli. Analysis of diethylstilbestrol, dienestrol and hexestrol in biological samples by immunoaffinity extraction and gas chromatography-negative-ion chemical ionization mass spectrometry. Journal of chromatography. 1990 May; 527(2):267-78. doi: 10.1016/s0378-4347(00)82111-8. [PMID: 2167323]
  • S Goldfarb, T D Pugh. Morphology and anatomic localization of renal microneoplasms and proximal tubule dysplasias induced by four different estrogens in the hamster. Cancer research. 1990 Jan; 50(1):113-9. doi: NULL. [PMID: 2152770]
  • E D Ramsey, J R Perkins, D E Games, J R Startin. Analysis of drug residues in tissue by combined supercritical-fluid extraction-supercritical-fluid chromatography-mass spectrometry-mass spectrometry. Journal of chromatography. 1989 Mar; 464(2):353-64. doi: 10.1016/s0021-9673(00)94253-5. [PMID: 2542348]
  • M P Mingeot-Leclercq, A Schanck, M F Ronveaux-Dupal, M Deleers, R Brasseur, J M Ruysschaert, G Laurent, P M Tulkens. Ultrastructural, physico-chemical and conformational study of the interactions of gentamicin and bis(beta-diethylaminoethylether) hexestrol with negatively-charged phospholipid layers. Biochemical pharmacology. 1989 Mar; 38(5):729-41. doi: 10.1016/0006-2952(89)90225-6. [PMID: 2539158]
  • C J Arts, P T Kemperman, H van den Berg. Oestrogen radioreceptor assay for multi-residue screening of bovine urine for oestrogenic anabolic compounds. Food additives and contaminants. 1989 Jan; 6(1):103-15. doi: 10.1080/02652038909373743. [PMID: 2536336]
  • J E Hart. Subacute toxicity of diethylstilboestrol and hexoestrol in the female rat, and the effects of clomiphene pretreatment. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1988 Mar; 26(3):227-32. doi: 10.1016/0278-6915(88)90123-8. [PMID: 2835297]
  • J Engel, H Schönenberger, F Lux, P Hilgard. Anticancer drugs: estrophilic cisplatin derivatives. Cancer treatment reviews. 1987 Dec; 14(3-4):275-83. doi: 10.1016/0305-7372(87)90018-1. [PMID: 2830970]
  • J E Hart. Vitamin K-dependent blood clotting changes in female rats treated with oestrogens. Thrombosis and haemostasis. 1987 Jun; 57(3):273-7. doi: 10.1055/s-0038-1651115. [PMID: 2821645]
  • J Hart. Hepatotoxicity of the synthetic oestrogen hexoestrol in the female rat. Archives of toxicology. 1986 Dec; 59(4):216-20. doi: 10.1007/bf00290541. [PMID: 3030234]
  • R H Van den Berg, E H Jansen, G Zomer, C Enkelaar-Willemsen, R Bothmiedema, R W Stephany. Identification of anabolic stilbene derivatives in bovine urine by high-performance liquid chromatography and off-line chemiluminescent immunochemical detection. Journal of chromatography. 1986 Jun; 360(2):449-51. doi: 10.1016/s0021-9673(00)91696-0. [PMID: 3016006]
  • A P Carter, J D Cottingham, S N Dixon, R J Heitzman. An improved radioimmunoassay for the anabolic agent hexoestrol, using a monoclonal antibody. Journal of veterinary pharmacology and therapeutics. 1985 Dec; 8(4):362-7. doi: 10.1111/j.1365-2885.1985.tb00968.x. [PMID: 3005606]
  • J G Liehr, A M Ballatore, B B Dague, A A Ulubelen. Carcinogenicity and metabolic activation of hexestrol. Chemico-biological interactions. 1985 Oct; 55(1-2):157-76. doi: 10.1016/s0009-2797(85)80125-3. [PMID: 2998630]
  • E H Jansen, R H van den Berg, H van Blitterswijk, R Both-Miedema, R W Stephany. A highly specific detection method for diethylstilbestrol in bovine urine by radioimmunoassay following high performance liquid chromatography. Food additives and contaminants. 1985 Oct; 2(4):271-81. doi: 10.1080/02652038509373556. [PMID: 2998898]
  • B Kessel, Y X Liu, X C Jia, A J Hsueh. Autocrine role of estrogens in the augmentation of luteinizing hormone receptor formation in cultured rat granulosa cells. Biology of reproduction. 1985 Jun; 32(5):1038-50. doi: 10.1095/biolreprod32.5.1038. [PMID: 2990583]
  • H Tobioka, R Kawashima. Hexestrol residues and metabolites in the tissues of wethers injected with hexestrol dicaprylate or hexestrol. Journal of animal science. 1985 Feb; 60(2):511-8. doi: 10.2527/jas1985.602511x. [PMID: 2985528]
  • K Y Hostetler, A S Pappu, J L Witztum. Diethylaminoethoxyhexestrol causes hypertriglyceridemia in guinea pigs. Biochimica et biophysica acta. 1985 Jan; 833(1):165-9. doi: 10.1016/0005-2760(85)90265-6. [PMID: 2981562]
  • M Nishikawa, K Seki, Y Matsuzawa, Y Minami, S Kawata, S Miyoshi, Y Imai, R Saitoh, S Noda, S Tamura. Effect of high doses of synthetic estrogen on lipid metabolism in castrated male rats. Lipids. 1984 Oct; 19(10):777-83. doi: 10.1007/bf02534471. [PMID: 6094942]
  • K Y Hostetler. Molecular studies of the induction of cellular phospholipidosis by cationic amphiphilic drugs. Federation proceedings. 1984 Aug; 43(11):2582-5. doi: NULL. [PMID: 6086409]
  • J J Li, S A Li. High incidence of hepatocellular carcinomas after synthetic estrogen administration in Syrian golden hamsters fed alpha-naphthoflavone: a new tumor model. Journal of the National Cancer Institute. 1984 Aug; 73(2):543-7. doi: 10.1093/jnci/73.2.543. [PMID: 6087011]
  • E H Jansen, R W Stephany. [Diethylstilbestrol in urine of slaughtered cattle]. Tijdschrift voor diergeneeskunde. 1984 May; 109(10):402-4. doi: NULL. [PMID: 6330929]
  • Y Tashiro, Y Watanabe, Y Enomoto. Experimental phospholipidosis induced by 4,4'-diethyl-aminoethoxyhexestrol. Morphological and biochemical interpretations. Acta pathologica japonica. 1983 Sep; 33(5):929-42. doi: ". [PMID: 6316720]
  • R J Heitzman. The absorption, distribution and excretion of anabolic agents. Journal of animal science. 1983 Jul; 57(1):233-8. doi: 10.2527/jas1983.571233x. [PMID: 6309728]
  • R J Heitzman, D J Harwood. Radioimmunoassay of hexoestrol residues in faeces, tissues and body fluids of bulls and steers. The Veterinary record. 1983 Feb; 112(6):120-3. doi: 10.1136/vr.112.6.120. [PMID: 6301136]
  • L Castagnetta, C D'Agostino, M Lo Casto, A Traina, R E Leake. Breast cancer: a comparison of response to endocrine therapy and oestrogen excretion patterns including unusual metabolites. British journal of cancer. 1981 Nov; 44(5):670-4. doi: 10.1038/bjc.1981.252. [PMID: 6274375]
  • D J Pope, A P Gilbert, D J Easter, R P Chan, J C Turner, S Gottfried, D V Parke. Bifluranol, a novel fluorinated bibenzyl anti-androgen, its chemistry and disposition in different animal species. The Journal of pharmacy and pharmacology. 1981 May; 33(5):297-301. doi: 10.1111/j.2042-7158.1981.tb13784.x. [PMID: 6116777]
  • S Higashi, Y Aizawa. Adrenal estrogens in relation to ovarian function. Japanese journal of pharmacology. 1980 Aug; 30(4):413-9. doi: 10.1254/jjp.30.413. [PMID: 6259393]
  • Y Matsuzawa, K Y Hostetler. Studies on drug-induced lipidosis: subcellular localization of phospholipid and cholesterol in the liver of rats treated with chloroquine or 4,4'-bis (diethylaminoethoxy)alpha, beta-diethyldiphenylethane. Journal of lipid research. 1980 Feb; 21(2):202-14. doi: 10.1016/s0022-2275(20)39826-6. [PMID: 6246184]
  • H Yoshida, M Shimada. [Clinical studies on serum lipids in the patients with tumor of the prostate gland. 2nd. Report. Changes of serum lipids and lipoprotein fractions during the treatment of estramustine phosphate disodium, hexestrol and diethylstilbestrol 4, 4-diphosphoric ester for the patients with prostatic cancer (author's transl)]. Nihon Hinyokika Gakkai zasshi. The japanese journal of urology. 1980 Jan; 71(1):59-69. doi: . [PMID: 6155501]
  • J B Dekanski. Anti-prostatic activity of bifluranol, a fluorinated bibenzyl. British journal of pharmacology. 1980; 71(1):11-6. doi: 10.1111/j.1476-5381.1980.tb10903.x. [PMID: 6258683]
  • H Galbraith, D G Dempster. Effect of hexoestrol on the response of finishing steers to treatment with trenbolone acetate. The Veterinary record. 1979 Sep; 105(12):283-4. doi: 10.1136/vr.105.12.283. [PMID: 516314]
  • W Frisch, R Lüllmann-Rauch. Differential effects of chloroquine and of several other amphiphilic cationic drugs upon rat choroid plexus. Acta neuropathologica. 1979 May; 46(3):203-8. doi: 10.1007/bf00690845. [PMID: 223364]
  • H Galbraith, H B Watson. Performance, blood and carcase characteristics of finishing steers treated with trenbolone acetate and hexoestrol. The Veterinary record. 1978 Jul; 103(2):28-31. doi: 10.1136/vr.103.2.28. [PMID: 685099]
  • C Wu. Estrogen induction of ornithine aminotransferase in rat kidney slices. Biochemical and biophysical research communications. 1978 Jun; 82(3):782-6. doi: 10.1016/0006-291x(78)90850-1. [PMID: 697772]
  • H B Tjiong, J Lepthin, H Debuch. Lysosomal phospholipids from rat liver after treatment with different drugs. Hoppe-Seyler's Zeitschrift fur physiologische Chemie. 1978 Jan; 359(1):63-9. doi: 10.1515/bchm.1978.359.1.63. [PMID: 627402]
  • K Pietrzik, C Hesse, D Hötzel. [Residue analysis of substances with estrogenic effects]. DTW. Deutsche tierarztliche Wochenschrift. 1976 May; 83(5):233-6. doi: NULL. [PMID: 776571]
  • A N Smirnov, O V Smirnova, V B Rozen. [Estradiol receptors in rat kidney, liver and uterus cytosol]. Doklady Akademii nauk SSSR. 1975 Jan; 220(1):244-7. doi: NULL. [PMID: 163175]
  • M Shirai, S Matsuda, S Mitsukawa, M Nakamura, K Yonezawa. Changes in plasma levels of FSH, LH and testosterone during anti-androgenic hormone therapy for patients with prostatic cancer. The Tohoku journal of experimental medicine. 1974 Oct; 114(2):145-58. doi: 10.1620/tjem.114.145. [PMID: 4612875]
  • J Frick. Improved plasma testosterone assay by competitive protein binding and clinical availability. Investigative urology. 1974 Jul; 12(1):27-9. doi: NULL. [PMID: 4835487]
  • Y Matsushita, K Hasegawa, R Sugimura, S Otomo, H Morii. Effect of calcitonin and hexestrol on urinary excretion of hydroxyproline in a patient with prostatic cancer and bone metastases. Endocrinologia japonica. 1974 Apr; 21(2):109-13. doi: 10.1507/endocrj1954.21.109. [PMID: 4408206]
  • T Taketomi, M Hayashi, N Kawamura, R Ichikawa. Abnormality in hepatic lipids of a patient having taken coralgil, (hexestrol bis (beta-diethylaminoethyl ether)) for a long period. The Japanese journal of experimental medicine. 1974 Apr; 44(2):133-43. doi: ". [PMID: 4366218]
  • A Yamamoto, K Seki, T Kitani, Y Matsuzawa, S Adachi. [Drug-induced lipidosis: formation of myeloid bodies (author's transl)]. Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme. 1974 Apr; 19(4):275-93. doi: ". [PMID: 4369542]
  • G B Koval'skiĭ. [Ovarian interstitial tissue in disordered sex hormone balance]. Arkhiv patologii. 1974; 36(2):53-8. doi: NULL. [PMID: 4155940]
  • Kh K Amineva, T B Zhuravleva. [Glandular hyperplasia of the endometrium in experimental hyperestrogenism]. Arkhiv patologii. 1974; 36(1):53-60. doi: NULL. [PMID: 4281295]
  • A M Serban, D Ioaniţiu. [Sterility and fertility in somatotropic hyperfunction]. Revue roumaine d'endocrinologie. 1973; 10(6):571-9. doi: NULL. [PMID: 4806817]
  • G D Braithwaite, R F Glascock, S Riazuddin. The effect of hexoestrol on calcium metabolism in the sheep. The British journal of nutrition. 1972 Sep; 28(2):269-73. doi: 10.1079/bjn19720034. [PMID: 4672324]
  • T Shikata, T Kanetaka, Y Endo, K Nagashima. Drug-induced generalized phospholipidosis. Acta pathologica japonica. 1972 Aug; 22(3):517-31. doi: 10.1111/j.1440-1827.1972.tb01849.x. [PMID: 4678598]
  • T Kitani, A Yamamoto, S Adachi, H Tako, T Imanaka. [Drug-induced lipidosis. IV. Morphological aspect of leukocytes and bone marrow cells in human cases and animal experiments induced by 4,4'-diethylaminoethoxy-hexestrol]. Nihon Ketsueki Gakkai zasshi : journal of Japan Haematological Society. 1972 Apr; 35(2):131-45. doi: . [PMID: 4350052]
  • S Adachi, Y Matsuzawa, T Yokomura, K Ishikawa, S Uhara. Studies on drug-induced lipodosis. V. Changes in the lipid composition of rat liver and spleen following the administration of 4,4'-diethylaminoethoxyhexestrol. Lipids. 1972 Jan; 7(1):1-7. doi: 10.1007/bf02531262. [PMID: 4335173]
  • A Yamamoto, S Adachi, K Ishikawa, T Yokomura, T Kitani. Studies on drug-induced lipidosis. 3. Lipid composition of the liver and some other tissues in clinical cases of 'Niemann-Pick-like syndrome' induced by 4,4'-diethylaminoethoxyhexestrol. Journal of biochemistry. 1971 Nov; 70(5):775-84. doi: 10.1093/oxfordjournals.jbchem.a129695. [PMID: 5144610]
  • M S Soloff, J E Creange, G O Potts. Unique estrogen-binding properties of rat pregnancy plasma. Endocrinology. 1971 Feb; 88(2):427-32. doi: 10.1210/endo-88-2-427. [PMID: 4322049]
  • S Imoto, S Hiraide, S Mitsutani, H Matsumoto, S Kaneko. [A case of drug-induced lipidosis with 'sea-blue histiocytes' in the bone marrow]. Naika hokan. Japanese archives of internal medicine. 1971; 18(3):83-108. doi: NULL. [PMID: 4935924]
  • T S Ermolova, L A Cherkasskiĭ. [Synestrol induced morphological changes in golden hamster kidneys]. Arkhiv patologii. 1970; 32(10):37-42. doi: NULL. [PMID: 5503769]
  • T S Ermolova, L A Cherkasskiĭ. [Morphogenesis of experimental renal tumors in golden hamsters]. Voprosy onkologii. 1970; 16(11):55-61. doi: NULL. [PMID: 5511344]
  • C A Hakim, M G Elder, D F Hawkins. Plasma factor IX levels in patients given hexoestrol or stilboestrol to suppress lactation. British medical journal. 1969 Oct; 4(5675):82-4. doi: 10.1136/bmj.4.5675.82. [PMID: 4898563]
  • K Uchida, M Kadowaki, K Miyata, T Miyake. Biphasic effect of estrogen on rat plasma cholesterol level and its interaction by androgen. Endocrinologia japonica. 1969 Feb; 16(1):211-4. doi: 10.1507/endocrj1954.16.211. [PMID: 5394329]
  • M D Serban, D Ioaniţiu, P Strihan, I Klepsch, E Stroe. [The hexestrol test in the diagnosis of primary amenorrhea]. Studii si cercetari de endocrinologie. 1969; 20(1):55-61. doi: NULL. [PMID: 5343646]
  • J A Brignone, C M de Brignone, A O Stoppani. [In vivo action of synthetic estrogens on the NADH2-oxidase system in rat organs]. Comptes rendus des seances de la Societe de biologie et de ses filiales. 1968; 162(8):1621-2. doi: NULL. [PMID: 4238202]
  • M D Serban, D Ioaniţiu. [Positive hexestrol test and subsequent pregnancy in a case of acromegaly]. Studii si cercetari de endocrinologie. 1968; 19(1):67-71. doi: NULL. [PMID: 5666400]
  • A Ia Olinia. [Excretion of hormones in patients with cancer of the breast after hormone loading with synestrol and cortisone]. Klinika i lechenie zlokachestvennykh novoobrazovanii. 1968; 11(?):93-104. doi: NULL. [PMID: 5725418]
  • K Uchida, M Kadowaki, K Miyata, T Miyake. [Biphasic effects of estrogens on the plasma cholesterol level in rats]. Nihon Naibunpi Gakkai zasshi. 1967 Jan; 42(10):1159-65. doi: 10.1507/endocrine1927.42.10_1159. [PMID: 6067756]
  • A M Serban. [Premises of the test of induced estrogenuria as a test of hypophyseal-ovarian function]. Studii si cercetari de endocrinologie. 1966; 17(3):253-5. doi: NULL. [PMID: 5950030]
  • A M Serban, D Ioaniţiu, E Stroe, I Klepsch. [Estrogenuria induced with hexestrol. Some results and deductions]. Studii si cercetari de endocrinologie. 1966; 17(4):359-68. doi: NULL. [PMID: 6010411]
  • V P Baskakova. [Conditioned reflex changes in the blood serum proteins under the effect of folliculin, synestrol, progesterone and testosteron-propionate]. Farmakologiia i toksikologiia. 1965 Sep; 28(5):566-8. doi: NULL. [PMID: 5875820]
  • A K KURALASOV. [ON CAUSES OF THE DEVELOPMENT OF RECURRENCE OF MAMMARY CANCER UNDER CONDITIONS OF HORMONE THERAPY]. Biulleten' eksperimental'noi biologii i meditsiny. 1964 Aug; 57(?):87-9. doi: NULL. [PMID: 14249888]
  • W L TRAXEL, V S LEQUIRE. IN VITRO ACTIVATION OF LIPOLYTIC ACTIVITY IN THE SERUM OF DOGS BY BILE SALTS. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1964 Jun; 116(?):388-92. doi: 10.3181/00379727-116-29256. [PMID: 14189146]
  • I K WANG, Y LIU, T C LI. [FEMALE SEX HORMONE THERAPY FOR PROSTATIC HYPERTROPHY]. Zhonghua wai ke za zhi [Chinese journal of surgery]. 1964 Mar; 12(?):295-9. doi: NULL. [PMID: 14173091]