ST 19:2;O3 (BioDeep_00000016688)

 

Secondary id: BioDeep_00000001275, BioDeep_00000002634, BioDeep_00000002966, BioDeep_00000014795, BioDeep_00001868515, BioDeep_00001868862, BioDeep_00001869450


代谢物信息卡片


(3S,7R,8R,9S,10R,13S,14S)-3,7-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one

化学式: C19H28O3 (304.2038338)
中文名称: 11-氧雄甾酮, 6,17-二羟基-6b,17b-雄甾-4-烯-3-酮, 11beta-羟基睾酮, 11-氧噻吩乙醇酮, 雄甾-5-烯-3beta,7beta-二醇-17-酮, 4-羟基-睾酮
谱图信息: 最多检出来源 Homo sapiens(blood) 0.22%

分子结构信息

SMILES: C1C(=O)C[C@]2([H])CC[C@@]3([H])[C@]4([H])CC[C@H](O)[C@@]4(C)CC[C@]3([H])[C@@]2(C)C1=O
InChI: InChI=1S/C19H28O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,16,21-22H,3-10H2,1-2H3/t11-,12-,13-,16-,18+,19-/m0/s1

描述信息

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
A 17beta-hydroxy steroid that is testosterone bearing an additional hydroxy substituent at the 6beta-position.
C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor
C274 - Antineoplastic Agent > C129818 - Antineoplastic Hormonal/Endocrine Agent > C481 - Antiestrogen
C274 - Antineoplastic Agent > C163758 - Targeted Therapy Agent > C1740 - Aromatase Inhibitor
C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor
C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist

同义名列表

55 个代谢物同义名

3alpha-Hydroxy-5alpha-androstane-11,17-dione; 3alpha-hydroxy-5alpha-Androstan-11,17-dione; Androstane-11,17-dione,3-hydroxy-, (3a,5a)-; 5alpha-Androstan-3alpha-ol-11,17-dione; 11-Ketoandrosterone; ST 19:2;O3; 6beta,17beta-dihydroxyandrost-4-en-3-one; 6beta-hydroxytestosterone; 6 β hydroxy testosterone; 3beta,17beta-dihydroxyandrost-4-en-3-one; 3-keto-androst-4ene-2beta 17beta-diol; 2beta-hydroxy-testosterone; 1beta,17beta-dihydroxyandrost-4-en-3-one; 1beta-hydroxytestosterone; 5alpha-androstan-16alpha-hydroxy-3,17dione; 5alpha-androstan-16alpha-ol-3,17-dione; 5beta-androstan-16alpha-hydroxy-3,17dione; 5beta-androstan-16alpha-ol-3,17-dione; 17beta-hydroxy-5beta-androstane-3,11-dione; 5beta-Androstane-17beta-ol-3,11-dione; 11-Keto-5beta-dihydrotestosterone; 16alpha,17beta-dihydroxyandrost-4-en-3-one; 4-androstene-16alpha,17beta-diol-3-one; 16alpha-Hydroxytestosterone; Androst-4-en-3-one,11,17-dihydroxy-, (11b,17b)-; 11beta,17beta-Dihydroxy-4-androsten-3-one; 4-androstene-11beta,17beta-diol-3-one; 11beta-Hydroxytestosterone; 3alpha-hydroxy-5beta-androstane-11,17-dione; 5beta-androstan-3-ol-11,17-dione; 11-Oxo etiocholanolone; 11-Ketoetiocholanolone; 17beta-hydroxyandrostan-3,11-dione; 11-Ketodihydrotestosterone; Adrenosterone-M; 11beta-hydroxyandrostan-3,17-dione; 11betaOH-5alpha-androstanedione; 17beta-hydroxy-5alpha-androstan-1,3-dione; 17-hydroxy-androstan-1,3-dione; 3beta,6alpha-dihydroxy-5alpha-androst-9(11)-en-17-one; (3S,7R,8R,9S,10R,13S,14S)-3,7-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-one; 7b-Hydroxydehydroepiandrosterone; 4-Hydroxy Testosterone; 4-Hydroxytestosterone; 7a-Hydroxydehydroepiandrosterone; 3a,16-Dihydroxyandrostenone; 3a,16b-Dihydroxyandrostenone; 3a,16a-Dihydroxyandrostenone; 16-Oxoandrostenediol; 17beta,19-dihydroxyandrost-4-en-3-one; 19-hydroxy-testosterone; 7alpha,17beta-dihydroxyandrost-4-en-3-one; 7alpha-Hydroxytestosterone; 3beta,16alpha-dihydroxy-5-androsten-17-one; 16alpha-Hydroxydehydroepiandrosterone



数据库引用编号

99 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(6)

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)

4 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

  • Patrick Caron, Véronique Turcotte, Chantal Guillemette. A quantitative analysis of total and free 11-oxygenated androgens and its application to human serum and plasma specimens using liquid-chromatography tandem mass spectrometry. Journal of chromatography. A. 2021 Aug; 1650(?):462228. doi: 10.1016/j.chroma.2021.462228. [PMID: 34090133]
  • Donna Elizabeth Sunny, Elke Hammer, Till Ittermann, Elisabeth Luise Krüger, Stephanie Hübner, Michaela Friederike Hartmann, Stefan Alexander Wudy, Uwe Völker, Matthias Heckmann. Fetal Zone Steroids and Estrogen Show Sex Specific Effects on Oligodendrocyte Precursor Cells in Response to Oxidative Damage. International journal of molecular sciences. 2021 Jun; 22(12):. doi: 10.3390/ijms22126586. [PMID: 34205405]
  • Paavo V H Raittinen, Heimo Syvälä, Teuvo L J Tammela, Merja R Häkkinen, Pauliina Ilmonen, Seppo Auriola, Teemu J Murtola. Atorvastatin induces adrenal androgen downshift in men with prostate cancer: A post Hoc analysis of a pilot adaptive Randomised clinical trial. EBioMedicine. 2021 Jun; 68(?):103432. doi: 10.1016/j.ebiom.2021.103432. [PMID: 34144486]
  • Stefano DE Luca, Eleonora Amante, Cristian Fiori, Giorgio Alleva, Eugenio Alladio, Federico Marini, Diletta Garrou, Matteo Manfredi, Daniele Amparore, Enrico Checcucci, Serena Pruner, Alberto Salomone, Roberto M Scarpa, Marco Vincenti, Francesco Porpiglia. Prospective evaluation of urinary steroids and prostate carcinoma-induced deviation: preliminary results. Minerva urology and nephrology. 2021 02; 73(1):98-106. doi: 10.23736/s2724-6051.19.03529-x. [PMID: 31833333]
  • Takashi Yazawa, Hiroyuki Inaba, Yoshitaka Imamichi, Toshio Sekiguchi, Junsuke Uwada, Mohammad Sayful Islam, Makoto Orisaka, Daisuke Mikami, Takanori Ida, Takahiro Sato, Yoshimichi Miyashiro, Satoru Takahashi, Md Rafiqul Islam Khan, Nobuo Suzuki, Akihiro Umezawa, Takeshi Kitano. Profiles of 5α-Reduced Androgens in Humans and Eels: 5α-Dihydrotestosterone and 11-Ketodihydrotestosterone Are Active Androgens Produced in Eel Gonads. Frontiers in endocrinology. 2021; 12(?):657360. doi: 10.3389/fendo.2021.657360. [PMID: 33833737]
  • Liyan Wang, Tingting Zhao, Yunxiang Wang, Banglian Hu, Jianfei Tao, Jinshan Ke, Tingfei Wei, Guangbo Ge, Qiang Meng, Changyuan Wang, Qi Liu, Huijun Sun, Jingjing Wu, Yanwei Chen. In vitro Measurement and In vivo Prediction of Time-Dependent Inhibitory Effects of Three Tyrosine Kinase Inhibitors on CYP3A Activity. Current drug metabolism. 2021; 22(10):802-810. doi: 10.2174/1389200222666210902130319. [PMID: 34473615]
  • Yao Fu, Xiaoxiao Tian, Lingling Han, Yilin Li, Ying Peng, Jiang Zheng. Mechanism-based inactivation of cytochrome P450 2D6 by Notopterol. Chemico-biological interactions. 2020 May; 322(?):109053. doi: 10.1016/j.cbi.2020.109053. [PMID: 32198085]
  • Mengjun Shi, Yiping Cui, Cunyu Liu, Changqin Li, Zhenhua Liu, Wen-Yi Kang. CYPs-mediated drug-drug interactions on psoralidin, isobavachalcone, neobavaisoflavone and daidzein in rats liver microsomes. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2020 Feb; 136(?):111027. doi: 10.1016/j.fct.2019.111027. [PMID: 31870919]
  • L I Velikanova, Z R Shafigullina, N V Vorokhobina, E V Malevanaya. Gas Chromatography-Mass Spectrometry Analysis of Urinary Steroid Metabolomics for Detection of Early Signs of Adrenal Neoplasm Malignancy in Patients with Cushing's Syndrome. Bulletin of experimental biology and medicine. 2019 Sep; 167(5):676-680. doi: 10.1007/s10517-019-04597-8. [PMID: 31630306]
  • Micaela B Ruiz, Gabina V Eguizábal, Daniel P Villarreal, Juan M Busso, Abel G López. Inhibitory action of thymol on fecal microbial activity in Tamandua tetradactyla and its effect on glucocorticoid metabolite measurement. General and comparative endocrinology. 2019 09; 280(?):91-96. doi: 10.1016/j.ygcen.2019.04.015. [PMID: 31002827]
  • Wahid Ali Khan, Gaffar Sarwar Zaman, Sultan Alouffi, Mohd Wajid Ali Khan. Depression and its related parameters increased the production of autoantibodies against 16α-hydroxyestrone-albumin complex in systemic lupus erythematosus. International immunopharmacology. 2019 Jun; 71(?):215-223. doi: 10.1016/j.intimp.2019.03.036. [PMID: 30925322]
  • Xavier de la Torre, Daniel Jardines, Davide Curcio, Cristiana Colamonici, Francesco Botrè. Isotope ratio mass spectrometry in antidoping analysis: The use of endogenous reference compounds. Rapid communications in mass spectrometry : RCM. 2019 Mar; 33(6):579-586. doi: 10.1002/rcm.8377. [PMID: 30589473]
  • Annekathrin Martina Keiler, Oliver Zierau, Sylvi Wolf, Patrick Diel, Wilhelm Schänzer, Günter Vollmer, David Machalz, Gerhard Wolber, Maria Kristina Parr. Androgen- and estrogen-receptor mediated activities of 4-hydroxytestosterone, 4-hydroxyandrostenedione and their human metabolites in yeast based assays. Toxicology letters. 2018 Aug; 292(?):39-45. doi: 10.1016/j.toxlet.2018.04.026. [PMID: 29702199]
  • K Adamcová, L Kolátorová, T Chlupáčová, M Šimková, H Jandíková, A Pařízek, L Stárka, M Dušková. Changes to fetal steroidogenesis caused by maternal smoking. Physiological research. 2017 09; 66(Suppl 3):S375-S386. doi: 10.33549/physiolres.933728. [PMID: 28948822]
  • Michael W O'Reilly, Punith Kempegowda, Carl Jenkinson, Angela E Taylor, Jonathan L Quanson, Karl-Heinz Storbeck, Wiebke Arlt. 11-Oxygenated C19 Steroids Are the Predominant Androgens in Polycystic Ovary Syndrome. The Journal of clinical endocrinology and metabolism. 2017 03; 102(3):840-848. doi: 10.1210/jc.2016-3285. [PMID: 27901631]
  • Ann Kathryn Korkidakis, Robert L Reid. Testosterone in Women: Measurement and Therapeutic Use. Journal of obstetrics and gynaecology Canada : JOGC = Journal d'obstetrique et gynecologie du Canada : JOGC. 2017 03; 39(3):124-130. doi: 10.1016/j.jogc.2017.01.006. [PMID: 28343552]
  • Therina du Toit, Liezl M Bloem, Jonathan L Quanson, Riaan Ehlers, Antonio M Serafin, Amanda C Swart. Profiling adrenal 11β-hydroxyandrostenedione metabolites in prostate cancer cells, tissue and plasma: UPC2-MS/MS quantification of 11β-hydroxytestosterone, 11keto-testosterone and 11keto-dihydrotestosterone. The Journal of steroid biochemistry and molecular biology. 2017 02; 166(?):54-67. doi: 10.1016/j.jsbmb.2016.06.009. [PMID: 27345701]
  • Ji-Zong Jiang, Bao-Hua Yang, Li-Li Ji, Li Yang, Yu-Chang Mao, Zhuo-Han Hu, Zheng-Tao Wang, Chang-Hong Wang. Metabolic-induced cytotoxicity of diosbulbin B in CYP3A4-expressing cells. Toxicology in vitro : an international journal published in association with BIBRA. 2017 Feb; 38(?):59-66. doi: 10.1016/j.tiv.2016.11.006. [PMID: 27836570]
  • Masayuki Tsujimoto, Chie Agawa, Shinya Ueda, Takayoshi Yamane, Haruna Kitayama, Aya Terao, Tomoya Fukuda, Tetsuya Minegaki, Kohshi Nishiguchi. Inhibitory Effects of Juices Prepared from Individual Vegetables on CYP3A4 Activity in Recombinant CYP3A4 and LS180 Cells. Biological & pharmaceutical bulletin. 2017; 40(9):1561-1565. doi: 10.1248/bpb.b17-00116. [PMID: 28867739]
  • Mari Hashimoto, Kaoru Kobayashi, Mana Yamazaki, Yasuhiro Kazuki, Shoko Takehara, Mitsuo Oshimura, Kan Chiba. Cyp3a deficiency enhances androgen receptor activity and cholesterol synthesis in the mouse prostate. The Journal of steroid biochemistry and molecular biology. 2016 10; 163(?):121-8. doi: 10.1016/j.jsbmb.2016.04.018. [PMID: 27137100]
  • Fu-Chun Yang, Yi-Lung Chen, Sen-Lin Tang, Chang-Ping Yu, Po-Hsiang Wang, Wael Ismail, Chia-Hsiang Wang, Jiun-Yan Ding, Cheng-Yu Yang, Chia-Ying Yang, Yin-Ru Chiang. Integrated multi-omics analyses reveal the biochemical mechanisms and phylogenetic relevance of anaerobic androgen biodegradation in the environment. The ISME journal. 2016 08; 10(8):1967-83. doi: 10.1038/ismej.2015.255. [PMID: 26872041]
  • Ajeeth K Pingili, Shyamala Thirunavukkarasu, Mehmet Kara, David D Brand, Akemi Katsurada, Dewan S A Majid, L Gabriel Navar, Frank J Gonzalez, Kafait U Malik. 6β-Hydroxytestosterone, a Cytochrome P450 1B1-Testosterone-Metabolite, Mediates Angiotensin II-Induced Renal Dysfunction in Male Mice. Hypertension (Dallas, Tex. : 1979). 2016 May; 67(5):916-26. doi: 10.1161/hypertensionaha.115.06936. [PMID: 26928804]
  • Yuyong Ke, Renaud Gonthier, Fernand Labrie. The conversion of 16β hydroxyldehydroepiandrosterone in human serum. Steroids. 2016 May; 109(?):50-5. doi: 10.1016/j.steroids.2016.02.007. [PMID: 26896786]
  • Anaïs Michaut, Dounia Le Guillou, Caroline Moreau, Simon Bucher, Mitchell R McGill, Sophie Martinais, Thomas Gicquel, Isabelle Morel, Marie-Anne Robin, Hartmut Jaeschke, Bernard Fromenty. A cellular model to study drug-induced liver injury in nonalcoholic fatty liver disease: Application to acetaminophen. Toxicology and applied pharmacology. 2016 Feb; 292(?):40-55. doi: 10.1016/j.taap.2015.12.020. [PMID: 26739624]
  • Ajeeth K Pingili, Mehmet Kara, Nayaab S Khan, Anne M Estes, Zongtao Lin, Wei Li, Frank J Gonzalez, Kafait U Malik. 6β-hydroxytestosterone, a cytochrome P450 1B1 metabolite of testosterone, contributes to angiotensin II-induced hypertension and its pathogenesis in male mice. Hypertension (Dallas, Tex. : 1979). 2015 Jun; 65(6):1279-87. doi: 10.1161/hypertensionaha.115.05396. [PMID: 25870196]
  • Xi-feng Zhang, Ju Liu, Feng Ye, Sen-guo Ji, Ni Zhang, Ru-sen Cao, Ling He, Jiang-chuan Wu, Xing-fu Li. Effects of triptolide on the pharmacokinetics of cyclophosphamide in rats: a possible role of cytochrome P3A4 inhibition. Chinese journal of integrative medicine. 2014 Jul; 20(7):534-9. doi: 10.1007/s11655-014-1710-0. [PMID: 24420925]
  • L Máčová, M Bičíková, H Zamrazilová, M Hill, H Kazihnitková, B Sedláčková, L Stárka. Reduced levels of circulating 7alpha-hydroxy-dehydroepiandrosterone in treated adolescent obese patients. Physiological research. 2014; 63(1):95-101. doi: 10.33549/physiolres.932540. [PMID: 24182335]
  • Jeffrey C Sivils, Tiffany M Ancrum, Lisa J Bain. LOSS of Mrp1 alters detoxification enzyme expression in a tissue- and hormonal-status-specific manner. Journal of applied toxicology : JAT. 2013 Aug; 33(8):766-73. doi: 10.1002/jat.2727. [PMID: 22522787]
  • Peter N Laver, André Ganswindt, Stefanie B Ganswindt, Kathleen A Alexander. Non-invasive monitoring of glucocorticoid metabolites in banded mongooses (Mungos mungo) in response to physiological and biological challenges. General and comparative endocrinology. 2012 Nov; 179(2):178-83. doi: 10.1016/j.ygcen.2012.08.011. [PMID: 22926328]
  • Thomas Piper, Andreas Thomas, Mario Thevis, Martial Saugy. Investigations on hydrogen isotope ratios of endogenous urinary steroids: reference-population-based thresholds and proof-of-concept. Drug testing and analysis. 2012 Sep; 4(9):717-27. doi: 10.1002/dta.1416. [PMID: 22991188]
  • André Ganswindt, Charlotte Muilwijk, Monique Engelkes, Stefanie Muenscher, Henk Bertschinger, Monique Paris, Rupert Palme, Elissa Z Cameron, Nigel C Bennett, Fredrik Dalerum. Validation of noninvasive monitoring of adrenocortical endocrine activity in ground-feeding aardwolves (Proteles cristata): exemplifying the influence of consumption of inorganic material for fecal steroid analysis. Physiological and biochemical zoology : PBZ. 2012 Mar; 85(2):194-9. doi: 10.1086/664591. [PMID: 22418711]
  • Herbert J Tobias, Ying Zhang, Richard J Auchus, J Thomas Brenna. Detection of synthetic testosterone use by novel comprehensive two-dimensional gas chromatography combustion-isotope ratio mass spectrometry. Analytical chemistry. 2011 Sep; 83(18):7158-65. doi: 10.1021/ac2015849. [PMID: 21846122]
  • Man Ho Choi, Ju-Yeon Moon, Sung-Hee Cho, Bong Chul Chung, Eun Jig Lee. Metabolic alteration of urinary steroids in pre- and post-menopausal women, and men with papillary thyroid carcinoma. BMC cancer. 2011 Aug; 11(?):342. doi: 10.1186/1471-2407-11-342. [PMID: 21824401]
  • Yonglong Han, Xiangle Meng, Dan Li, Zhiyong Zhou, Qi Yu, Yan Li, Cheng Guo. [In vitro inhibition of five traditional Chinese medicine injections on rat liver microsomal CYP3A]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 Feb; 36(4):492-5. doi: . [PMID: 21598550]
  • Yogesh Kumar Katare, Alexander P Scott, Alyson J Laframboise, Weiming Li, Zena Alyasha'e, Christopher B Caputo, Stephen J Loeb, Barbara Zielinski. Release of free and conjugated forms of the putative pheromonal steroid 11-oxo-etiocholanolone by reproductively mature male round goby (Neogobius melanostomus Pallas, 1814). Biology of reproduction. 2011 Feb; 84(2):288-98. doi: 10.1095/biolreprod.110.086546. [PMID: 20944082]
  • Marie Bicikova, Richard Hampl, Martin Hill, Daniela Ripova, Pavel Mohr, Zdenek Putz. Neuro- and immunomodulatory steroids and other biochemical markers in drug-naive schizophrenia patients and the effect of treatment with atypical antipsychotics. Neuro endocrinology letters. 2011; 32(2):141-7. doi: . [PMID: 21552193]
  • Yassar Farooq, Gordon C K Roberts. Kinetics of electron transfer between NADPH-cytochrome P450 reductase and cytochrome P450 3A4. The Biochemical journal. 2010 Dec; 432(3):485-93. doi: 10.1042/bj20100744. [PMID: 20879989]
  • Furong Qiu, Rong Zhang, Guangji Wang, Chenglu Gao, Jianguo Sun, Jian Jiang, Yueming Ma. Activation of CYP3A-mediated testosterone 6β-hydroxylation by tanshinone IIA and midazolam 1-hydroxylation by cryptotanshinone in human liver microsomes. Xenobiotica; the fate of foreign compounds in biological systems. 2010 Dec; 40(12):800-6. doi: 10.3109/00498254.2010.519062. [PMID: 20964620]
  • Pieter Van Renterghem, Peter Van Eenoo, Pierre-Edouard Sottas, Martial Saugy, Frans Delbeke. Subject-based steroid profiling and the determination of novel biomarkers for DHT and DHEA misuse in sports. Drug testing and analysis. 2010 Nov; 2(11-12):582-8. doi: 10.1002/dta.206. [PMID: 21204290]
  • Marie-Odile M Chelini, Emma Otta, Clarissa Yamakita, Rupert Palme. Sex differences in the excretion of fecal glucocorticoid metabolites in the Syrian hamster. Journal of comparative physiology. B, Biochemical, systemic, and environmental physiology. 2010 Aug; 180(6):919-25. doi: 10.1007/s00360-010-0467-9. [PMID: 20336462]
  • Birgit Flauger, Konstanze Krueger, Hartmut Gerhards, Erich Möstl. Simplified method to measure glucocorticoid metabolites in faeces of horses. Veterinary research communications. 2010 Feb; 34(2):185-95. doi: 10.1007/s11259-010-9344-y. [PMID: 20182914]
  • Monica Mazzarino, Maria Cristina Braganò, Francesco Donati, Xavier de la Torre, Francesco Botrè. Effects of propyphenazone and other non-steroidal anti-inflammatory agents on the synthetic and endogenous androgenic anabolic steroids urinary excretion and/or instrumental detection. Analytica chimica acta. 2010 Jan; 657(1):60-8. doi: 10.1016/j.aca.2009.10.022. [PMID: 19951758]
  • Lance Brooker, Maria Kristina Parr, Adam Cawley, Ulrich Flenker, Christopher Howe, Rymantas Kazlauskas, Wilhelm Schänzer, Adrian George. Development of criteria for the detection of adrenosterone administration by gas chromatography-mass spectrometry and gas chromatography-combustion-isotope ratio mass spectrometry for doping control. Drug testing and analysis. 2009 Nov; 1(11-12):587-95. doi: 10.1002/dta.108. [PMID: 20355175]
  • Noura Meklat, Jean-Claude Tabet, Jacques de Ceaurriz. Urine ratio of tetrahydrocortisol to tetrahydrodeoxycortisol to screen for the systemic administration of cortisone and hydrocortisone. Forensic science international. 2009 Mar; 185(1-3):e13-7. doi: 10.1016/j.forsciint.2008.12.011. [PMID: 19185436]
  • C Buisson, C Mongongu, C Frelat, M Jean-Baptiste, J de Ceaurriz. Isotope ratio mass spectrometry analysis of the oxidation products of the main and minor metabolites of hydrocortisone and cortisone for antidoping controls. Steroids. 2009 Mar; 74(3):393-7. doi: 10.1016/j.steroids.2008.11.001. [PMID: 19056411]
  • Jeremy W Tomlinson, Joanne Finney, Christopher Gay, Beverly A Hughes, Susan V Hughes, Paul M Stewart. Impaired glucose tolerance and insulin resistance are associated with increased adipose 11beta-hydroxysteroid dehydrogenase type 1 expression and elevated hepatic 5alpha-reductase activity. Diabetes. 2008 Oct; 57(10):2652-60. doi: 10.2337/db08-0495. [PMID: 18633104]
  • M Nováková, R Palme, H Kutalová, L Janský, D Frynta. The effects of sex, age and commensal way of life on levels of fecal glucocorticoid metabolites in spiny mice (Acomys cahirinus). Physiology & behavior. 2008 Sep; 95(1-2):187-93. doi: 10.1016/j.physbeh.2008.05.017. [PMID: 18586285]
  • Esther G van de Kerkhof, Inge A M de Graaf, Anna-Lena B Ungell, Geny M M Groothuis. Induction of metabolism and transport in human intestine: validation of precision-cut slices as a tool to study induction of drug metabolism in human intestine in vitro. Drug metabolism and disposition: the biological fate of chemicals. 2008 Mar; 36(3):604-13. doi: 10.1124/dmd.107.018820. [PMID: 18094037]
  • Lyubomir G Nashev, Charlie Chandsawangbhuwana, Zoltan Balazs, Atanas G Atanasov, Bernhard Dick, Felix J Frey, Michael E Baker, Alex Odermatt. Hexose-6-phosphate dehydrogenase modulates 11beta-hydroxysteroid dehydrogenase type 1-dependent metabolism of 7-keto- and 7beta-hydroxy-neurosteroids. PloS one. 2007 Jun; 2(6):e561. doi: 10.1371/journal.pone.0000561. [PMID: 17593962]
  • Maxie Kohler, Maria K Parr, Georg Opfermann, Mario Thevis, Nils Schlörer, Franz-Josef Marner, Wilhelm Schänzer. Metabolism of 4-hydroxyandrostenedione and 4-hydroxytestosterone: Mass spectrometric identification of urinary metabolites. Steroids. 2007 Mar; 72(3):278-86. doi: 10.1016/j.steroids.2006.11.018. [PMID: 17207827]
  • T L Klug, E Bågeman, C Ingvar, C Rose, H Jernström. Moderate coffee and alcohol consumption improves the estrogen metabolite profile in adjuvant treated breast cancer patients: a pilot study comparing pre- and post-operative levels. Molecular genetics and metabolism. 2006 Dec; 89(4):381-9. doi: 10.1016/j.ymgme.2006.08.005. [PMID: 16978896]
  • Yoshihiro Uesawa, Kiminori Mohri. The use of heat treatment to eliminate drug interactions due to grapefruit juice. Biological & pharmaceutical bulletin. 2006 Nov; 29(11):2274-8. doi: 10.1248/bpb.29.2274. [PMID: 17077528]
  • Toshiyuki Shimizu, Kei Akimoto, Takuya Yoshimura, Takuro Niwa, Kaoru Kobayashi, Michio Tsunoo, Kan Chiba. Autoinduction of MKC-963 [(R)-1-(1-cyclohexylethylamino)-4-phenylphthalazine] metabolism in healthy volunteers and its retrospective evaluation using primary human hepatocytes and cDNA-expressed enzymes. Drug metabolism and disposition: the biological fate of chemicals. 2006 Jun; 34(6):950-4. doi: 10.1124/dmd.105.007997. [PMID: 16531475]
  • Thomas M Polasek, John O Miners. Quantitative prediction of macrolide drug-drug interaction potential from in vitro studies using testosterone as the human cytochrome P4503A substrate. European journal of clinical pharmacology. 2006 Mar; 62(3):203-8. doi: 10.1007/s00228-005-0091-x. [PMID: 16416302]
  • Hanspeter W Steinmetz, Werner Kaumanns, Illona Dix, Michael Heistermann, Mark Fox, Franz-Josef Kaup. Coat condition, housing condition and measurement of faecal cortisol metabolites--a non-invasive study about alopecia in captive rhesus macaques (Macaca mulatta). Journal of medical primatology. 2006 Feb; 35(1):3-11. doi: 10.1111/j.1600-0684.2005.00141.x. [PMID: 16430489]
  • Kazuhiko Hanada, Rie Ogawa, Kishin Son, Yuuki Sasaki, Akashi Kikkawa, Shiho Ichihara, Hiroyasu Ogata. Effects of indoxylsulfate on the in vitro hepatic metabolism of various compounds using human liver microsomes and hepatocytes. Nephron. Physiology. 2006; 103(4):p179-86. doi: 10.1159/000092919. [PMID: 16645322]
  • Ralf Peter Meyer, Christoph Eugen Hagemeyer, Rolf Knoth, Michel Rene Kaufmann, Benedikt Volk. Anti-epileptic drug phenytoin enhances androgen metabolism and androgen receptor expression in murine hippocampus. Journal of neurochemistry. 2006 Jan; 96(2):460-72. doi: 10.1111/j.1471-4159.2005.03555.x. [PMID: 16336225]
  • Boaz Robinzon, Russell A Prough. Interactions between dehydroepiandrosterone and glucocorticoid metabolism in pig kidney: nuclear and microsomal 11beta-hydroxysteroid dehydrogenases. Archives of biochemistry and biophysics. 2005 Oct; 442(1):33-40. doi: 10.1016/j.abb.2005.07.010. [PMID: 16137639]
  • John Dulos, Monique A J van der Vleuten, Annemieke Kavelaars, Cobi J Heijnen, Annemieke M Boots. CYP7B expression and activity in fibroblast-like synoviocytes from patients with rheumatoid arthritis: regulation by proinflammatory cytokines. Arthritis and rheumatism. 2005 Mar; 52(3):770-8. doi: 10.1002/art.20950. [PMID: 15751070]
  • Luboslav Stárka, Richard Hampl, Miroslav Hanus, Michaela Matousková, Martin Hill. Plasma levels of 7-hydroxymetabolites of dehydroepiandrosterone in healthy Central European aging men. Clinical chemistry and laboratory medicine. 2005; 43(11):1218-22. doi: 10.1515/cclm.2005.211. [PMID: 16232089]
  • Jakub Hert, Martin Hill, Richard Hampl. Gas chromatographic-mass spectrometric identification of 16alpha-hydroxy-dehydroepiandrosterone in human seminal plasma. Steroids. 2004 Oct; 69(11-12):773-7. doi: 10.1016/j.steroids.2004.05.017. [PMID: 15579330]
  • Almut Schulze, Barbara Nicke, Patricia H Warne, Simon Tomlinson, Julian Downward. The transcriptional response to Raf activation is almost completely dependent on Mitogen-activated Protein Kinase Kinase activity and shows a major autocrine component. Molecular biology of the cell. 2004 Jul; 15(7):3450-63. doi: 10.1091/mbc.e03-11-0807. [PMID: 15090615]
  • Marie Bicíková, Daniela Rípová, Martin Hill, Roman Jirák, Helena Havlíková, Jaroslava Tallová, Richard Hampl. Plasma levels of 7-hydroxylated dehydroepiandrosterone (DHEA) metabolites and selected amino-thiols as discriminatory tools of Alzheimer's disease and vascular dementia. Clinical chemistry and laboratory medicine. 2004 May; 42(5):518-24. doi: 10.1515/cclm.2004.088. [PMID: 15202788]
  • Marie-Agnès Pelissier, Catherine Trap, Marie-Irène Malewiak, Robert Morfin. Antioxidant effects of dehydroepiandrosterone and 7alpha-hydroxy-dehydroepiandrosterone in the rat colon, intestine and liver. Steroids. 2004 Feb; 69(2):137-44. doi: 10.1016/j.steroids.2003.12.006. [PMID: 15013692]
  • B H Jung, S W Bai, B C Chung. Endogenous urinary steroids in premenopausal women with uterine leiomyomas. International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics. 2004 Jan; 84(1):55-60. doi: 10.1016/s0020-7292(03)00336-9. [PMID: 14698830]
  • Ivan Sterzl, Richard Hampl, Martin Hill, Pavlína Hrdá, Petr Matucha. Immunomodulatory cytokines in human seminal plasma correlate with immunomodulatory steroids. Steroids. 2003 Oct; 68(9):725-31. doi: 10.1016/s0039-128x(03)00114-4. [PMID: 14625004]
  • 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]
  • Taekrho Kim, Shellie M Callahan, Kishor M Wasan, Lane J Brunner. Effect of high-density lipoprotein associated cyclosporine on hepatic metabolism and renal function. PDA journal of pharmaceutical science and technology. 2003 Sep; 57(5):341-50. doi: . [PMID: 14677627]
  • Boaz Robinzon, Kristy K Michael, Sharon L Ripp, Stephen J Winters, Russell A Prough. Glucocorticoids inhibit interconversion of 7-hydroxy and 7-oxo metabolites of dehydroepiandrosterone: a role for 11beta-hydroxysteroid dehydrogenases?. Archives of biochemistry and biophysics. 2003 Apr; 412(2):251-8. doi: 10.1016/s0003-9861(03)00056-0. [PMID: 12667489]
  • Richard Hampl, Michal Pohanka, Martin Hill, Luboslav Stárka. The content of four immunomodulatory steroids and major androgens in human semen. The Journal of steroid biochemistry and molecular biology. 2003 Feb; 84(2-3):307-16. doi: 10.1016/s0960-0760(03)00044-x. [PMID: 12711017]
  • Michal Pohanka, Richard Hampl, Ivan Sterzl, Luboslav Stárka. Steroid hormones in human semen with particular respect to dehydroepiandrosterone and its immunomodulatory metabolites. Endocrine regulations. 2002 Jun; 36(2):79-86. doi: . [PMID: 12207557]
  • Andrew A Shaw, Stephen D Hall, Michael R Franklin, Raymond E Galinsky. The influence of L-glutamine on the depression of hepatic cytochrome P450 activity in male rats caused by total parenteral nutrition. Drug metabolism and disposition: the biological fate of chemicals. 2002 Feb; 30(2):177-82. doi: 10.1124/dmd.30.2.177. [PMID: 11792688]
  • M Hill, O Lapcík, H Havlíková, R Morfin, R Hampl. 7-Hydroxydehydroepiandrosterone epimers in human serum and saliva. Comparison of gas chromatography-mass spectrometry and radioimmunoassay. Journal of chromatography. A. 2001 Nov; 935(1-2):297-307. doi: 10.1016/s0021-9673(01)01106-2. [PMID: 11762781]
  • N I Bahr, R Palme, U Möhle, J K Hodges, M Heistermann. Comparative aspects of the metabolism and excretion of cortisol in three individual nonhuman primates. General and comparative endocrinology. 2000 Mar; 117(3):427-38. doi: 10.1006/gcen.1999.7431. [PMID: 10764553]
  • R B Ibrahim, J G Wilson, M E Thorsby, D J Edwards. Effect of buprenorphine on CYP3A activity in rat and human liver microsomes. Life sciences. 2000 Feb; 66(14):1293-8. doi: 10.1016/s0024-3205(00)00436-7. [PMID: 10755464]
  • O Lapcík, R Hampl, M Hill, L Stárka. Immunoassay of 7-hydroxysteroids: 2. Radioimmunoassay of 7alpha-hydroxy-dehydroepiandrosterone. The Journal of steroid biochemistry and molecular biology. 1999 Dec; 71(5-6):231-7. doi: 10.1016/s0960-0760(99)00145-4. [PMID: 10704912]
  • W Goymann, E Möstl, T Van't Hof, M L East, H Hofer. Noninvasive fecal monitoring of glucocorticoids in spotted hyenas, Crocuta crocuta. General and comparative endocrinology. 1999 Jun; 114(3):340-8. doi: 10.1006/gcen.1999.7268. [PMID: 10336822]
  • B Wallner, E Möstl, J Dittami, H Prossinger. Fecal glucocorticoids document stress in female Barbary macaques (Macaca sylvanus). General and comparative endocrinology. 1999 Jan; 113(1):80-6. doi: 10.1006/gcen.1998.7183. [PMID: 9882546]
  • I A Glass, R C Lam, T Chang, E Roitman, L J Shapiro, C H Shackleton. Steroid sulphatase deficiency is the major cause of extremely low oestriol production at mid-pregnancy: a urinary steroid assay for the discrimination of steroid sulphatase deficiency from other causes. Prenatal diagnosis. 1998 Aug; 18(8):789-800. doi: . [PMID: 9742566]
  • S Attal-Khémis, V Dalmeyda, J L Michot, M Roudier, R Morfin. Increased total 7 alpha-hydroxy-dehydroepiandrosterone in serum of patients with Alzheimer's disease. The journals of gerontology. Series A, Biological sciences and medical sciences. 1998 Mar; 53(2):B125-32. doi: 10.1093/gerona/53a.2.b125. [PMID: 9520908]
  • S Attal-Khémis, V Dalmeyda, R Morfin. Change of 7alpha-hydroxy-dehydroepiandrosterone levels in serum of mice treated by cytochrome P450-modifying agents. Life sciences. 1998; 63(17):1543-53. doi: 10.1016/s0024-3205(98)00421-4. [PMID: 9808065]
  • N Tagawa, S Kusuda, Y Kobayashi. C16 hydroxylation of 3beta-hydroxy-delta5-steroids during the early neonatal period. Biological & pharmaceutical bulletin. 1997 Dec; 20(12):1295-9. doi: 10.1248/bpb.20.1295. [PMID: 9448107]
  • C J Newton. Estrogen receptor blockade by the pure antiestrogen, ZM 182780, induces death of pituitary tumour cells. The Journal of steroid biochemistry and molecular biology. 1995 Dec; 55(3-4):327-36. doi: 10.1016/0960-0760(95)00191-3. [PMID: 8541229]
  • M D Green, E M Oturu, T R Tephly. Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates. Drug metabolism and disposition: the biological fate of chemicals. 1994 Sep; 22(5):799-805. doi: NULL. [PMID: 7835232]
  • B H Mason, I M Holdaway, S J Skinner, R G Kay. The relationship of urinary and plasma androgens to steroid receptors and menopausal status in breast cancer patients and their influence on survival. Breast cancer research and treatment. 1994; 32(2):203-12. doi: 10.1007/bf00665771. [PMID: 7865850]
  • R K Brantley, J C Wingfield, A H Bass. Sex steroid levels in Porichthys notatus, a fish with alternative reproductive tactics, and a review of the hormonal bases for male dimorphism among teleost fishes. Hormones and behavior. 1993 Sep; 27(3):332-47. doi: 10.1006/hbeh.1993.1025. [PMID: 8225257]
  • M Kodama, T Kodama, R Totani, Y Aso. The regularity of intersteroidal relations in urine as related to the law of mass action. In vivo (Athens, Greece). 1991 Mar; 5(2):127-36. doi: NULL. [PMID: 1837484]
  • K Hirato, T Yanaihara. Serum steroid hormone levels in neonates born from the mother with placental sulfatase deficiency. Endocrinologia japonica. 1990 Oct; 37(5):731-9. doi: 10.1507/endocrj1954.37.731. [PMID: 2150812]
  • I Mayer, B Borg, R Schulz. Seasonal changes in and effect of castration/androgen replacement on the plasma levels of five androgens in the male three-spined stickleback, Gasterosteus aculeatus L. General and comparative endocrinology. 1990 Jul; 79(1):23-30. doi: 10.1016/0016-6480(90)90084-y. [PMID: 2354778]
  • D E Kime, L O Larsen. Effect of gonadectomy and hypophysectomy on plasma steroid levels in male and female lampreys (Lampetra fluviatilis, L.). General and comparative endocrinology. 1987 Nov; 68(2):189-96. doi: 10.1016/0016-6480(87)90028-1. [PMID: 2962897]
  • H Vanderstichele, W Eechaute, E Lacroix, I Leusen. Influence of neonatal androgenization on the testicular steroidogenesis in the adult rat. Journal of steroid biochemistry. 1987 Oct; 28(4):421-7. doi: 10.1016/0022-4731(87)91060-0. [PMID: 2959818]
  • R C Cochran. Serum androgens during the annual reproductive cycle of the male mummichog, Fundulus heteroclitus. General and comparative endocrinology. 1987 Jan; 65(1):141-8. doi: 10.1016/0016-6480(87)90233-4. [PMID: 3803896]
  • S T Chan, W S Yeung. A new method for the simultaneous determination of androstenedione, testosterone, 11-oxotestosterone and 11 beta-OH-testosterone in fish plasma using combined techniques of Celite chromatography and radioimmunoassay. Journal of steroid biochemistry. 1986 Dec; 25(6):1013-21. doi: 10.1016/0022-4731(86)90338-9. [PMID: 3795949]
  • R Schulz. In vitro metabolism of steroid hormones in the liver and in blood cells of male rainbow trout (Salmo gairdneri Richardson). General and comparative endocrinology. 1986 Nov; 64(2):312-9. doi: 10.1016/0016-6480(86)90019-5. [PMID: 3557096]
  • E A Zbella, J Ilekis, A Scommegna, R Benveniste. Competitive studies with dehydroepiandrosterone sulfate and 16 alpha-hydroxydehydroepiandrosterone sulfate in cultured human choriocarcinoma JEG-3 cells: effect on estrone, 17 beta-estradiol, and estriol secretion. The Journal of clinical endocrinology and metabolism. 1986 Sep; 63(3):751-7. doi: 10.1210/jcem-63-3-751. [PMID: 2942557]
  • R Schlaghecke, H K Kley, H L Krüskemper. The measurement of 11 beta, 17 beta-dihydroxy-4-androsten-3-one (11 beta-hydroxytestosterone) by radioimmunoassay in human plasma. Journal of clinical chemistry and clinical biochemistry. Zeitschrift fur klinische Chemie und klinische Biochemie. 1986 Aug; 24(8):577-81. doi: 10.1515/cclm.1986.24.8.577. [PMID: 3760788]
  • T Akiyama, M Hashino, E Kawamura, T Kosaki, T Yanaihara, T Nakayama, H Mori. [Determination of serum 16 alpha-hydroxydehydroepiandrosterone, 16 alpha-hydroxyestrone and estriol by gas chromatography-mass spectrometry and their perinatal movement]. Nihon Sanka Fujinka Gakkai zasshi. 1986 Apr; 38(4):505-12. doi: . [PMID: 2939158]
  • H V Henning, H Ludwig-Köhn. Neutral steroid metabolites in body fluids of patients with uremia and after renal transplantation. Contributions to nephrology. 1986; 50(?):153-66. doi: 10.1159/000412996. [PMID: 3542370]
  • P M Rosenblum, L Yamada, I P Callard, G V Callard. Validation of radioimmunoassay systems for the measurement of 11-keto- and 11 beta-hydroxytestosterone in teleost blood. Comparative biochemistry and physiology. B, Comparative biochemistry. 1985; 82(4):659-65. doi: 10.1016/0305-0491(85)90504-8. [PMID: 4092434]