Summary: 17 beta-Hydroxy-4-androsten-3-ones. Testosterone derivatives formed by the substitution of one or more hydroxyl groups in any position.

Top Publications

  1. Magnusson M, Sandström R. Quantitative analysis of eight testosterone metabolites using column switching and liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2004;18:1089-94 pubmed
    ..The formation rates of 16alpha-, 16beta-hydroxytestosterone and androstenedione were quantified, and 2beta-and 6beta-hydroxytestosterone were formed above the limits of detection. ..
  2. Vail R, Homann M, Hanna I, Zaks A. Preparative synthesis of drug metabolites using human cytochrome P450s 3A4, 2C9 and 1A2 with NADPH-P450 reductase expressed in Escherichia coli. J Ind Microbiol Biotechnol. 2005;32:67-74 pubmed
    ..Conversion yields of 29-93% were obtained from 1-L reactions, enabling isolation of 59 mg 6beta-hydroxytestosterone, 110 mg 4'-hydroxydiclofenac and 88 mg acetaminophen...
  3. Scarth J, Spencer H, Hudson S, Teale P, Gray B, Hillyer L. The application of in vitro technologies to study the metabolism of the androgenic/anabolic steroid stanozolol in the equine. Steroids. 2010;75:57-69 pubmed publisher
  4. Young B, Bryan M, Sower S, Scott A, Li W. 15alpha-hydroxytestosterone induction by GnRH I and GnRH III in Atlantic and Great Lakes sea lamprey (Petromyzon marinus L.). Gen Comp Endocrinol. 2004;136:276-81 pubmed
    ..These are the first data to show a response of a C19 steroid to GnRH stimulation in sea lamprey. ..
  5. Manavalan T, Teng Y, Litchfield L, Muluhngwi P, Al Rayyan N, Klinge C. Reduced expression of miR-200 family members contributes to antiestrogen resistance in LY2 human breast cancer cells. PLoS ONE. 2013;8:e62334 pubmed publisher
  6. Qiu F, Zhang R, Wang G, Gao C, Sun J, Jiang J, et al. Activation of CYP3A-mediated testosterone 6?-hydroxylation by tanshinone IIA and midazolam 1-hydroxylation by cryptotanshinone in human liver microsomes. Xenobiotica. 2010;40:800-6 pubmed publisher
    ..Additionally, these data allow for an accurate prediction of the magnitude and likelihood of Danshen-drug interactions. ..
  7. Corbin C, Mapes S, Marcos J, Shackleton C, Morrow D, Safe S, et al. Paralogues of porcine aromatase cytochrome P450: a novel hydroxylase activity is associated with the survival of a duplicated gene. Endocrinology. 2004;145:2157-64 pubmed
    ..It probably represents an evolutionary gain of function associated with fixation and the survival of the genes after CYP19 duplication. Novel activities and adaptive functions may exist among other duplicated vertebrate aromatases. ..
  8. Kim B, Kim D, Park R, Kwon K, Ryu D, Kim Y, et al. Effect of an extract of the root of Scutellaria baicalensis and its flavonoids on aflatoxin B1 oxidizing cytochrome P450 enzymes. Planta Med. 2001;67:396-9 pubmed
    ..These results demonstrated that the extract of the root of Scutellaria baicalensis has a specific inhibitory effect on CYP1A1/2 among CYP enzymes involved in AFB1 metabolism by rat and human microsomes. ..
  9. Soars M, Petullo D, Eckstein J, Kasper S, Wrighton S. An assessment of udp-glucuronosyltransferase induction using primary human hepatocytes. Drug Metab Dispos. 2004;32:140-8 pubmed
    ..The clinical relevance of the induction responses obtained in this study is unclear. ..

More Information


  1. Chottanapund S, van Duursen M, Navasumrit P, Hunsonti P, Timtavorn S, Ruchirawat M, et al. Effect of androgens on different breast cancer cells co-cultured with or without breast adipose fibroblasts. J Steroid Biochem Mol Biol. 2013;138:54-62 pubmed publisher
    ..The results suggest that androgens that cannot be aromatized, like DHT, may provide a perspective for treatment of breast cancer patients, especially those with triple negative breast cancer. ..
  2. Ayyanathan K, Lechner M, Bell P, Maul G, Schultz D, Yamada Y, et al. Regulated recruitment of HP1 to a euchromatic gene induces mitotically heritable, epigenetic gene silencing: a mammalian cell culture model of gene variegation. Genes Dev. 2003;17:1855-69 pubmed
    ..Thus, like variegation in Drosophila, recruitment of mammalian HP1 to a euchromatic promoter can establish a silenced state that is epigenetically heritable. ..
  3. Al Awadi S, Afzal M, Oommen S. Studies on Bacillus stearothermophilus. Part III. Transformation of testosterone. Appl Microbiol Biotechnol. 2003;62:48-52 pubmed
    ..These metabolites were purified by TLC and HPLC followed by their identification using (1)H- and (13)C-NMR and other spectroscopic data. ..
  4. Wang D, Zhang M. Rapid quantitation of testosterone hydroxyl metabolites by ultra-performance liquid chromatography and mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2007;855:290-4 pubmed
    ..This method is applicable to the measurement of the testosterone hydroxylase activity in biological matrices such as the liver microsome incubates. ..
  5. Horinouchi M, Hayashi T, Koshino H, Kurita T, Kudo T. Identification of 9,17-dioxo-1,2,3,4,10,19-hexanorandrostan-5-oic acid, 4-hydroxy-2-oxohexanoic acid, and 2-hydroxyhexa-2,4-dienoic acid and related enzymes involved in testosterone degradation in Comamonas testosteroni TA441. Appl Environ Microbiol. 2005;71:5275-81 pubmed
  6. Wang H, Xu D, Peng R, Yue J. Testosterone-metabolizing capacity and characteristics of adrenal microsomes in human fetus in vitro. J Pediatr Endocrinol Metab. 2010;23:143-52 pubmed
  7. Garcia M, Rager J, Wang Q, Strab R, Hidalgo I, Owen A, et al. Cryopreserved human hepatocytes as alternative in vitro model for cytochrome p450 induction studies. In Vitro Cell Dev Biol Anim. 2003;39:283-7 pubmed
    ..The results suggest that cryopreserved human hepatocytes can be a suitable in vitro model for evaluating xenobiotics as inducers of CYP1A1/2 and CYP3A4 enzymes. ..
  8. Sakamoto K, Kim K, Verma R, Ransick A, Stein B, Crews C, et al. Development of Protacs to target cancer-promoting proteins for ubiquitination and degradation. Mol Cell Proteomics. 2003;2:1350-8 pubmed
    ..Future improvements to this technology may yield a general approach to treat a number of human diseases, including cancer. ..
  9. Schmidt M, Fernandez De Mattos S, van der Horst A, Klompmaker R, Kops G, Lam E, et al. Cell cycle inhibition by FoxO forkhead transcription factors involves downregulation of cyclin D. Mol Cell Biol. 2002;22:7842-52 pubmed
    ..Ectopic expression of cyclin D1 can partially overcome FoxO factor-induced cell cycle arrest, demonstrating that downregulation of D-type cyclins represents a physiologically relevant mechanism of FoxO-induced cell cycle inhibition. ..
  10. LeBlanc G, McLachlan J. Changes in the metabolic elimination profile of testosterone following exposure of the crustacean Daphnia magna to tributyltin. Ecotoxicol Environ Saf. 2000;45:296-303 pubmed
  11. Chen C, Thakker D. The fallacy of using adrenochrome reaction for measurement of reactive oxygen species formed during cytochrome p450-mediated metabolism of xenobiotics. J Pharmacol Exp Ther. 2002;300:417-20 pubmed
    ..Together, these results lead to the conclusion that the use of adrenochrome reaction for measurement of reactive oxygen species formed during CYP3A4-mediated metabolism of xenobiotics is inappropriate. ..
  12. Engman H, Lennernas H, Taipalensuu J, Otter C, Leidvik B, Artursson P. CYP3A4, CYP3A5, and MDR1 in human small and large intestinal cell lines suitable for drug transport studies. J Pharm Sci. 2001;90:1736-51 pubmed
  13. Lowartz S, Renaud R, Beamish F, Leatherland J. Evidence for 15alpha- and 7alpha-hydroxylase activity in gonadal tissue of the early-life stages of sea lampreys, Petromyzon marinus. Comp Biochem Physiol B Biochem Mol Biol. 2004;138:119-27 pubmed
    ..Testosterone was not present in the incubation medium from either ovarian or testis fragments incubated with any of the substrates used...
  14. Schanzer W, Horning S, Donike M. Metabolism of anabolic steroids in humans: synthesis of 6 beta-hydroxy metabolites of 4-chloro-1,2-dehydro-17 alpha-methyltestosterone, fluoxymesterone, and metandienone. Steroids. 1995;60:353-66 pubmed
  15. Storbeck K, Bloem L, Africander D, Schloms L, Swart P, Swart A. 11?-Hydroxydihydrotestosterone and 11-ketodihydrotestosterone, novel C19 steroids with androgenic activity: a putative role in castration resistant prostate cancer?. Mol Cell Endocrinol. 2013;377:135-46 pubmed publisher
  16. Okabe H, Hasunuma M, Hashimoto Y. The hepatic and intestinal metabolic activities of P450 in rats with surgery- and drug-induced renal dysfunction. Pharm Res. 2003;20:1591-4 pubmed
  17. Morfin R, Lafaye P, Cotillon A, Nato F, Chmielewski V, Pompon D. 7 alpha-hydroxy-dehydroepiandrosterone and immune response. Ann N Y Acad Sci. 2000;917:971-82 pubmed
  18. Kim J, Lee J, Nam H, Choi H, Yang J, Lee J, et al. SUMOylation of pontin chromatin-remodeling complex reveals a signal integration code in prostate cancer cells. Proc Natl Acad Sci U S A. 2007;104:20793-8 pubmed
    ..These data clearly define a functional model and provide a link between SUMO modification and prostate cancer progression. ..
  19. Schulze A, Nicke B, Warne P, Tomlinson S, Downward J. The transcriptional response to Raf activation is almost completely dependent on Mitogen-activated Protein Kinase Kinase activity and shows a major autocrine component. Mol Biol Cell. 2004;15:3450-63 pubmed
    ..The use of transcriptional profiling in this way allows detailed analysis of the architecture of signaling pathways to be undertaken. ..
  20. Turcu A, Mallappa A, Elman M, Avila N, Marko J, Rao H, et al. 11-Oxygenated Androgens Are Biomarkers of Adrenal Volume and Testicular Adrenal Rest Tumors in 21-Hydroxylase Deficiency. J Clin Endocrinol Metab. 2017;102:2701-2710 pubmed publisher
    ..8; P < 0.0001). 11oxC19 steroids and PregS might serve as clinically useful biomarkers of disease control and long-term complications in 21OHD. ..
  21. Di Marco A, Marcucci I, Verdirame M, Perez J, Sanchez M, Pelaez F, et al. Development and validation of a high-throughput radiometric CYP3A4/5 inhibition assay using tritiated testosterone. Drug Metab Dispos. 2005;33:349-58 pubmed
    ..This assay thus represents a high-throughput version of the classical testosterone 6beta-hydroxylation assay, which is the most widely used method to assess the potential for CYP3A4/5 inhibition of new chemical entities. ..
  22. Mirkov S, Komoroski B, Ramirez J, Graber A, Ratain M, Strom S, et al. Effects of green tea compounds on irinotecan metabolism. Drug Metab Dispos. 2007;35:228-33 pubmed
    ..Catechins do not induce CYP3A4 activity. The effect of acute and prolonged use of green tea on the pharmacokinetics of irinotecan in patients remains to be evaluated. ..
  23. Rock D, Foti R, Pearson J. The combination of chemical and antibody inhibitors for superior P450 3A inhibition in reaction phenotyping studies. Drug Metab Dispos. 2008;36:2410-3 pubmed publisher
    ..Herein, the combination of chemical plus antibody inhibitors is explored to find whether P450 3A could be selectively and completely (>99%) inhibited by using both inhibitors simultaneously. ..
  24. Soucek L, Nasi S, Evan G. Omomyc expression in skin prevents Myc-induced papillomatosis. Cell Death Differ. 2004;11:1038-45 pubmed
    ..These findings indicate that it is possible to selectively enhance the intrinsic apoptotic pathway mediated by Myc and so quell its oncogenic action. ..
  25. An G, Ng A, Meka C, Luo G, Bright S, Cazares L, et al. Cloning and characterization of UROC28, a novel gene overexpressed in prostate, breast, and bladder cancers. Cancer Res. 2000;60:7014-20 pubmed
    ..This gene did not demonstrate increased expression in lung and colon cancer tissues. ..
  26. Vaziri Gohar A, Houston K. GPER1-mediated IGFBP-1 induction modulates IGF-1-dependent signaling in tamoxifen-treated breast cancer cells. Mol Cell Endocrinol. 2016;422:160-171 pubmed publisher
    ..These results suggested that 4-OHT inhibits IGF-1 signaling via GPER1 and CREB mediated extracellular IGFBP-1 accumulation in breast cancer cells. ..
  27. Kanayama N, Todo K, Reth M, Ohmori H. Reversible switching of immunoglobulin hypermutation machinery in a chicken B cell line. Biochem Biophys Res Commun. 2005;327:70-5 pubmed
    ..Starting from a single DT40-SW cell, Ig gene repertoire was efficiently diversified during culture only when AID expression was on. ..
  28. Lin W, Karsten U, Goletz S, Cheng R, Cao Y. Co-expression of CD173 (H2) and CD174 (Lewis Y) with CD44 suggests that fucosylated histo-blood group antigens are markers of breast cancer-initiating cells. Virchows Arch. 2010;456:403-9 pubmed publisher
    ..The results show that in these tissues CD173 (H2) and CD174 (LeY) are associated with CD44 expression, suggesting that these carbohydrate antigens are markers of cancer-initiating cells or of early progenitors of breast carcinomas. ..
  29. Guenthner C, Miyamichi K, Yang H, Heller H, Luo L. Permanent genetic access to transiently active neurons via TRAP: targeted recombination in active populations. Neuron. 2013;78:773-84 pubmed publisher
    ..When combined with tools for labeling, tracing, recording, and manipulating neurons, TRAP offers a powerful approach for understanding how the brain processes information and generates behavior. ..
  30. Klug T, Bågeman E, Ingvar C, Rose C, Jernstrom H. 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. Mol Genet Metab. 2006;89:381-9 pubmed
  31. Pelengaris S, Abouna S, Cheung L, Ifandi V, Zervou S, Khan M. Brief inactivation of c-Myc is not sufficient for sustained regression of c-Myc-induced tumours of pancreatic islets and skin epidermis. BMC Biol. 2004;2:26 pubmed
    ..Together, these results suggest that treatment schedules will need to be informed by knowledge of the molecular basis and environmental context of any given cancer. ..
  32. Ivanova M, Mazhawidza W, Dougherty S, Minna J, Klinge C. Activity and intracellular location of estrogen receptors alpha and beta in human bronchial epithelial cells. Mol Cell Endocrinol. 2009;305:12-21 pubmed publisher
    ..In conclusion, the response of HBECs to ER ligands is gender-independent suggesting that estrogenic sensitivity may be acquired during lung carcinogenesis. ..
  33. Mwinyi J, Cavaco I, Yurdakok B, Mkrtchian S, Ingelman Sundberg M. The ligands of estrogen receptor ? regulate cytochrome P4502C9 (CYP2C9) expression. J Pharmacol Exp Ther. 2011;338:302-9 pubmed publisher
    ..Taken together, these results indicate that ER? and its ligands play an important role in the regulation of CYP2C9 expression. ..
  34. Wójcikowski J, Haduch A, Daniel W. Effect of classic and atypical neuroleptics on cytochrome P450 3A (CYP3A) in rat liver. Pharmacol Rep. 2012;64:1411-8 pubmed
    ..The observed changes in the CYP3A expression after prolonged exposition to neuroleptics suggest their influence on the enzyme regulation. ..
  35. Sarkis R, Honiger J, Chafai N, Baudrimont M, Sarkis K, Delelo R, et al. Semiautomatic macroencapsulation of fresh or cryopreserved porcine hepatocytes maintain their ability for treatment of acute liver failure. Cell Transplant. 2001;10:601-7 pubmed
    ..Cryopreserved cells were as efficient as fresh hepatocytes. ..
  36. Akiyoshi T, Saito T, Murase S, Miyazaki M, Murayama N, Yamazaki H, et al. Comparison of the inhibitory profiles of itraconazole and cimetidine in cytochrome P450 3A4 genetic variants. Drug Metab Dispos. 2011;39:724-8 pubmed publisher
  37. Ringel M, Oesch F, Gerl M, Klebach M, Quint M, Bader A, et al. Permissive and suppressive effects of dexamethasone on enzyme induction in hepatocyte co-cultures. Xenobiotica. 2002;32:653-66 pubmed
    ..However, a large interlaboratory variation is known. Our study provides evidence that differences in glucocorticoid concentration in the culture medium contribute to this variation. ..
  38. Liu T, Deng D, Lin Z, Pan Y, Zhou W, Zhou W, et al. [Effect of shengbanfang on CYP3A1 activities of Sprague-Dawley rat]. Zhong Yao Cai. 2012;35:254-9 pubmed
    ..Shengbanfang has no induce effect on the enzymic activity of CYP3Al in SD rats. ..
  39. Uesawa Y, Mohri K. The use of heat treatment to eliminate drug interactions due to grapefruit juice. Biol Pharm Bull. 2006;29:2274-8 pubmed
    ..No significant increase in the AUC of NFP was observed in the rats given heat-treated GJ. These results suggest that the heat treatment of GJ reduces the concentrations of FCs, thus eliminating the potential for drug interactions...
  40. McKinney M, Arukwe A, De Guise S, Martineau D, Béland P, Dallaire A, et al. Characterization and profiling of hepatic cytochromes P450 and phase II xenobiotic-metabolizing enzymes in beluga whales (Delphinapterus leucas) from the St. Lawrence River Estuary and the Canadian Arctic. Aquat Toxicol. 2004;69:35-49 pubmed
    ..CA animals demonstrated similar, immunologically cross-reactive phase I and II hepatic enzyme profiles, which is suggestive of the importance of metabolism in the toxicokinetics and fate of xenobiotics in animals from both populations ..
  41. Watanabe K, Motoya E, Matsuzawa N, Funahashi T, Kimura T, Matsunaga T, et al. Marijuana extracts possess the effects like the endocrine disrupting chemicals. Toxicology. 2005;206:471-8 pubmed
    ..01-1000 nM. These results indicate that there are some metabolic interactions between cannabinoid and steroid metabolism and that the constituents showing estrogen-like activity exist in marijuana. ..
  42. Riquelme P, Wundt J, Hutchinson J, Brulport M, Jun Y, Sotnikova A, et al. A refined characterisation of the NeoHepatocyte phenotype necessitates a reappraisal of the transdifferentiation hypothesis. Differentiation. 2009;77:263-76 pubmed publisher
  43. McClellan K, Markham A. Finasteride: a review of its use in male pattern hair loss. Drugs. 1999;57:111-26 pubmed
    ..With its generally good tolerability profile, finasteride is a new approach to the management of this condition, for which treatment options are few. Its role relative to topical minoxidil has yet to be determined. ..
  44. Quinkler M, Diederich S, Bahr V, Oelkers W. The role of progesterone metabolism and androgen synthesis in renal blood pressure regulation. Horm Metab Res. 2004;36:381-6 pubmed
    ..Locally produced androgens might be responsible for the observed difference in blood pressure between men and women and higher susceptibility to hypertension in men. ..
  45. Hirunpanich V, Katagi J, Sethabouppha B, Sato H. Demonstration of docosahexaenoic acid as a bioavailability enhancer for CYP3A substrates: in vitro and in vivo evidence using cyclosporin in rats. Drug Metab Dispos. 2006;34:305-10 pubmed
    ..It was thus demonstrated that DHA could be used as a BA enhancer for the drugs that are extensively metabolized by CYP3A in the gut. ..
  46. Hengstler J, Ringel M, Biefang K, Hammel S, Milbert U, Gerl M, et al. Cultures with cryopreserved hepatocytes: applicability for studies of enzyme induction. Chem Biol Interact. 2000;125:51-73 pubmed
  47. Furuta T, Suzuki A, Matsuzawa M, Shibasaki H, Kasuya Y. Syntheses of stable isotope-labeled 6 beta-hydroxycortisol, 6 beta-hydroxycortisone, and 6 beta-hydroxytestosterone. Steroids. 2003;68:693-703 pubmed
  48. Schwarz D, Kisselev P, Schunck W, Chernogolov A, Boidol W, Cascorbi I, et al. Allelic variants of human cytochrome P450 1A1 (CYP1A1): effect of T461N and I462V substitutions on steroid hydroxylase specificity. Pharmacogenetics. 2000;10:519-30 pubmed
  49. Fell J, Heathcock C. Oxidative fragmentation of pregna-14,16-dien-20-ones to 14 beta-hydroxyandrost-15-en-17-ones. J Org Chem. 2002;67:4742-6 pubmed
    ..This process is illustrated by the two-step conversion of dienone 1 into hydroxy ketone 11 in 51% overall yield (Scheme 5) and by the analogous conversion of dienone 13 into hydroxy ketone 24 in 61% overall yield (Scheme 11). ..
  50. Zhang X, Ding L, Kang L, Wang Z. Estrogen receptor-alpha 36 mediates mitogenic antiestrogen signaling in ER-negative breast cancer cells. PLoS ONE. 2012;7:e30174 pubmed publisher
  51. Geier M, Braun A, Fladischer P, Stepniak P, Rudroff F, Hametner C, et al. Double site saturation mutagenesis of the human cytochrome P450 2D6 results in regioselective steroid hydroxylation. FEBS J. 2013;280:3094-108 pubmed publisher
    ..pastoris for biocatalytic applications and to study so far unknown pharmacokinetic effects of individual and combined mutations in these key enzymes of the human drug metabolism. ..
  52. Pollock K, Stroemer P, Patel S, Stevanato L, Hope A, Miljan E, et al. A conditionally immortal clonal stem cell line from human cortical neuroepithelium for the treatment of ischemic stroke. Exp Neurol. 2006;199:143-55 pubmed
    ..These data indicate that CTX0E03 has the appropriate biological and manufacturing characteristics necessary for development as a therapeutic cell line. ..
  53. Martignoni M, Groothuis G, de Kanter R. Comparison of mouse and rat cytochrome P450-mediated metabolism in liver and intestine. Drug Metab Dispos. 2006;34:1047-54 pubmed
    ..Moreover, we show that intestinal slices are a useful in vitro technique to study gut metabolism. ..