androstenols

Summary

Summary: Unsaturated androstanes which are substituted with one or more hydroxyl groups in any position in the ring system.

Top Publications

  1. Shinohara K, Morofushi M, Funabashi T, Mitsushima D, Kimura F. Effects of 5alpha-androst-16-en-3alpha-ol on the pulsatile secretion of luteinizing hormone in human females. Chem Senses. 2000;25:465-7 pubmed
    ..The frequency of the LH pulse in the follicular phase was decreased by exposing the women to 3alpha-androstenol. ..
  2. Reid A, Attard G, Danila D, Oommen N, Olmos D, Fong P, et al. Significant and sustained antitumor activity in post-docetaxel, castration-resistant prostate cancer with the CYP17 inhibitor abiraterone acetate. J Clin Oncol. 2010;28:1489-95 pubmed publisher
    ..Abiraterone acetate has significant antitumor activity in post-docetaxel patients with CRPC. Randomized, phase III trials of abiraterone acetate are underway to define the future role of this agent. ..
  3. Urban N, Chamberlin B, Ramage S, Roberts Z, Loria R, Beckman M. Effects of alpha/beta-androstenediol immune regulating hormones on bone remodeling and apoptosis in osteoblasts. J Steroid Biochem Mol Biol. 2008;110:223-9 pubmed publisher
    ..In conclusion, alpha-AED opposed beta-AED by elevating a bone resorption scenario in osteoblast cells. The increase in RANKL/OPG is modulated by an activation of PPAR-gamma that in turn caused mild apoptosis of FOB-9 cells. ..
  4. Raghavan D, Klein E. Prostate cancer: moving forward by reinventing the wheel...but this time it is round. J Clin Oncol. 2008;26:4535-6 pubmed publisher
  5. Attard G, Reid A, Auchus R, Hughes B, Cassidy A, Thompson E, et al. Clinical and biochemical consequences of CYP17A1 inhibition with abiraterone given with and without exogenous glucocorticoids in castrate men with advanced prostate cancer. J Clin Endocrinol Metab. 2012;97:507-16 pubmed publisher
    ..Addition of dexamethasone reverses toxicity and could further suppress androgens by preventing a rise in substrates of backdoor androgen synthesis. ..
  6. Attard G, Reid A, A Hern R, Parker C, Oommen N, Folkerd E, et al. Selective inhibition of CYP17 with abiraterone acetate is highly active in the treatment of castration-resistant prostate cancer. J Clin Oncol. 2009;27:3742-8 pubmed publisher
    ..CYP17 blockade by abiraterone acetate results in declines in PSA and CTC counts and radiologic responses, confirming that CRPC commonly remains hormone driven. ..
  7. Noonan K, North S, Bitting R, Armstrong A, Ellard S, Chi K. Clinical activity of abiraterone acetate in patients with metastatic castration-resistant prostate cancer progressing after enzalutamide. Ann Oncol. 2013;24:1802-7 pubmed publisher
    ..Primary progression on enzalutamide may not preclude a response to abiraterone. ..
  8. Loria R. Antiglucocorticoid function of androstenetriol. Psychoneuroendocrinology. 1997;22 Suppl 1:S103-8 pubmed
    ..Only beta AET could markedly potentiate the cellular response by increasing lymphocyte activation and counteracting the immnosuppressive activity of hydrocortisone on lymphocyte proliferation and cytokine production. ..
  9. Mostaghel E, Marck B, Plymate S, Vessella R, Balk S, Matsumoto A, et al. Resistance to CYP17A1 inhibition with abiraterone in castration-resistant prostate cancer: induction of steroidogenesis and androgen receptor splice variants. Clin Cancer Res. 2011;17:5913-25 pubmed publisher

More Information

Publications62

  1. Efstathiou E, Titus M, Tsavachidou D, Tzelepi V, Wen S, Hoang A, et al. Effects of abiraterone acetate on androgen signaling in castrate-resistant prostate cancer in bone. J Clin Oncol. 2012;30:637-43 pubmed publisher
    ..Potential admixture of blood with bone marrow aspirate limits our ability to determine the origin of measured testosterone. ..
  2. Danila D, Morris M, de Bono J, Ryan C, Denmeade S, Smith M, et al. Phase II multicenter study of abiraterone acetate plus prednisone therapy in patients with docetaxel-treated castration-resistant prostate cancer. J Clin Oncol. 2010;28:1496-501 pubmed publisher
    ..The incidence of mineralocorticoid-related toxicities (hypertension or hypokalemia) was reduced by adding low-dose prednisone. The combination of AA plus prednisone is recommended for phase III investigations. ..
  3. Jacob S, Garcia S, Hayreh D, McClintock M. Psychological effects of musky compounds: comparison of androstadienone with androstenol and muscone. Horm Behav. 2002;42:274-83 pubmed
  4. Padgett D, Loria R. In vitro potentiation of lymphocyte activation by dehydroepiandrosterone, androstenediol, and androstenetriol. J Immunol. 1994;153:1544-52 pubmed
    ..DHEA did not counteract hydrocortisone activity whereas AED showed moderate antiglucocorticoid function. ..
  5. Acharya M, Gonzalez M, Mannens G, De Vries R, Lopez C, Griffin T, et al. A phase I, open-label, single-dose, mass balance study of 14C-labeled abiraterone acetate in healthy male subjects. Xenobiotica. 2013;43:379-89 pubmed publisher
    ..22% of TR). Major components of TR in faeces were unchanged AA (55.3% of TR) and abiraterone (22.3% of TR). Mean recovery of TR in faeces was 87.9%, indicating faeces as primary route of excretion. ..
  6. Ahlem C, Auci D, Mangano K, Reading C, Frincke J, Stickney D, et al. HE3286: a novel synthetic steroid as an oral treatment for autoimmune disease. Ann N Y Acad Sci. 2009;1173:781-90 pubmed publisher
    ..HE3286 may provide a new treatment option for patients with inflammatory and autoimmune diseases. ..
  7. Attard G, Reid A, Olmos D, de Bono J. Antitumor activity with CYP17 blockade indicates that castration-resistant prostate cancer frequently remains hormone driven. Cancer Res. 2009;69:4937-40 pubmed publisher
    ..Biomarker studies, including the analysis of ETS gene fusion status, on patients treated with abiraterone acetate may allow enrichment of patients with a sensitive phenotype in future studies of therapeutics targeting CYP17. ..
  8. Attard G, Reid A, Yap T, Raynaud F, Dowsett M, Settatree S, et al. Phase I clinical trial of a selective inhibitor of CYP17, abiraterone acetate, confirms that castration-resistant prostate cancer commonly remains hormone driven. J Clin Oncol. 2008;26:4563-71 pubmed publisher
    ..To evaluate this, a trial of abiraterone acetate-a potent, selective, small-molecule inhibitor of cytochrome P (CYP) 17, a key enzyme in androgen synthesis-was pursued...
  9. de Bono J, Logothetis C, Molina A, Fizazi K, North S, Chu L, et al. Abiraterone and increased survival in metastatic prostate cancer. N Engl J Med. 2011;364:1995-2005 pubmed publisher
    ..Funded by Cougar Biotechnology; COU-AA-301 ClinicalTrials.gov number, NCT00638690.). ..
  10. Ryan C, Smith M, Fong L, Rosenberg J, Kantoff P, Raynaud F, et al. Phase I clinical trial of the CYP17 inhibitor abiraterone acetate demonstrating clinical activity in patients with castration-resistant prostate cancer who received prior ketoconazole therapy. J Clin Oncol. 2010;28:1481-8 pubmed publisher
    ..Abiraterone acetate was well tolerated and demonstrated activity in CRPC, including in patients previously treated with ketoconazole. Continued clinical study is warranted. ..
  11. Offner H, Zamora A, Drought H, Matejuk A, Auci D, Morgan E, et al. A synthetic androstene derivative and a natural androstene metabolite inhibit relapsing-remitting EAE. J Neuroimmunol. 2002;130:128-39 pubmed
    ..These observations suggest that HE2500 and/or HE2200 limit the production of autoimmune Th1 associated cytokines, and ultimately may be beneficial for patients with MS or other autoimmune diseases. ..
  12. Loriot Y, Bianchini D, Ileana E, Sandhu S, Patrikidou A, Pezaro C, et al. Antitumour activity of abiraterone acetate against metastatic castration-resistant prostate cancer progressing after docetaxel and enzalutamide (MDV3100). Ann Oncol. 2013;24:1807-12 pubmed publisher
    ..3-4.1). Of the 12 patients assessable radiologically, only 1 (8%) attained a confirmed partial response. Abiraterone and prednisolone have modest antitumour activities in patients with mCRPC pretreated with docetaxel and enzalutamide. ..
  13. Soifer H, Souleimanian N, Wu S, Voskresenskiy A, Collak F, Cinar B, et al. Direct regulation of androgen receptor activity by potent CYP17 inhibitors in prostate cancer cells. J Biol Chem. 2012;287:3777-87 pubmed publisher
  14. Holterhus P, Piefke S, Hiort O. Anabolic steroids, testosterone-precursors and virilizing androgens induce distinct activation profiles of androgen responsive promoter constructs. J Steroid Biochem Mol Biol. 2002;82:269-75 pubmed
    ..We conclude that steroid-specific differences in gene transcription profiles due to androgen receptor activation could contribute to differences in biological actions of androgens. ..
  15. Ando S, De Amicis F, Rago V, Carpino A, Maggiolini M, Panno M, et al. Breast cancer: from estrogen to androgen receptor. Mol Cell Endocrinol. 2002;193:121-8 pubmed
    ..Taken together these data demonstrate that gonadal androgens antagonize MCF-7 proliferation induced by E(2). This seems to be related to the inhibitory effects of the over-expressed AR on E(2) genomic action. ..
  16. Ang J, Olmos D, de Bono J. CYP17 blockade by abiraterone: further evidence for frequent continued hormone-dependence in castration-resistant prostate cancer. Br J Cancer. 2009;100:671-5 pubmed publisher
  17. Kharbanda S, Band V, Murugesan K, Farooq A. Modulation of steroid production in goat ovarian cells: effect of progestins and antiprogestins. Endocr Res. 1990;16:293-309 pubmed
    ..Moreover, different antiprogestin had different effect on the modulation of steroid production. ..
  18. Luo W, Diaz F, Wiltbank M. Induction of mRNA for chemokines and chemokine receptors by prostaglandin F2? is dependent upon stage of the porcine corpus luteum and intraluteal progesterone. Endocrinology. 2011;152:2797-805 pubmed publisher
    ..In conclusion, PGF(2?) increases mRNA for chemokines and chemokine receptors in mature CL with similar PGF(2?) effects induced in early CL if intraluteal P4 is suppressed prior to PGF(2?) treatment...
  19. Cavalcanti G, Leal F, Garrido B, Padilha M, de Aquino Neto F. Detection of designer steroid methylstenbolone in "nutritional supplement" using gas chromatography and tandem mass spectrometry: elucidation of its urinary metabolites. Steroids. 2013;78:228-33 pubmed publisher
    ..These metabolites were detectable after one week post administration while unchanged methylstenbolone was only detectable in a brief period of 45 h. ..
  20. Petrylak D. Current clinical trials in castrate-resistant prostate cancer. Curr Urol Rep. 2011;12:173-9 pubmed publisher
    ..The challenge for the development of clinical trials will be how these compounds will be sequenced in the future. ..
  21. Thomas J, Boswell E, Scaccia L, Pletnev V, Umland T. Identification of key amino acids responsible for the substantially higher affinities of human type 1 3beta-hydroxysteroid dehydrogenase/isomerase (3beta-HSD1) for substrates, coenzymes, and inhibitors relative to human 3beta-HSD2. J Biol Chem. 2005;280:21321-8 pubmed
    ..These structure and function relationships can be used in future docking studies to design better inhibitors of the 3beta-HSD1 that may be useful in the treatment of hormone-sensitive cancers and preterm labor. ..
  22. Mennerick S, He Y, Jiang X, Manion B, Wang M, Shute A, et al. Selective antagonism of 5alpha-reduced neurosteroid effects at GABA(A) receptors. Mol Pharmacol. 2004;65:1191-7 pubmed
    ..laevis tadpoles. Analogous to benzodiazepine site antagonists, the development of neurosteroid antagonists may help clarify the role of GABA-potentiating neurosteroids in health and disease. ..
  23. De Bosschere H, Ducatelle R, Tshamala M, Coryn M. The use of epostane in an attempt to reproduce cystic endometrial hyperplasia in the bitch. Vet Res Commun. 2003;27:527-38 pubmed
    ..Therefore, it is suggested that deficient luteinization of the corpus luteum may be the trigger in the pathogenesis of CEH, as the secretion of varying amounts of sex steroids depends on the degree of luteinization. ..
  24. Sartor O. Combination therapy: Abiraterone prolongs survival in metastatic prostate cancer. Nat Rev Clin Oncol. 2011;8:515-6 pubmed publisher
    ..The survival gain observed in this pivotal trial is accomplished with few adverse events and conclusively demonstrates that patients with castration levels of serum testosterone remain sensitive to additional hormonal manipulation. ..
  25. Molitor B, Börgermann C. [Second line therapy for castration-resistant prostate cancer (CRPC)]. Urologe A. 2012;51:357-62 pubmed publisher
    ..More prospective clinical data will provide a large variety of different therapy combinations, sequence therapies or other therapy regimens particularly for selected subgroups of patients with castration-resistant prostate cancer. ..
  26. Diel P, Friedel A, Geyer H, Kamber M, Laudenbach Leschowsky U, Schanzer W, et al. Characterisation of the pharmacological profile of desoxymethyltestosterone (Madol), a steroid misused for doping. Toxicol Lett. 2007;169:64-71 pubmed
    ..Therefore, there is a need for a strict control of a possible misuse. ..
  27. Courtney K, Taplin M. The evolving paradigm of second-line hormonal therapy options for castration-resistant prostate cancer. Curr Opin Oncol. 2012;24:272-7 pubmed publisher
    ..Novel inhibitors of extra-gonadal androgen synthesis and androgen receptor function demonstrate the continued importance of androgen signaling in CRPC. These agents have improved clinical outcomes for patients with metastatic CRPC. ..
  28. Plich M, Klein R. Renal artery stenting with two simultaneous protection devices. Catheter Cardiovasc Interv. 2008;71:264-7 pubmed publisher
    ..No complications were observed and the final result was good. The concomitant use of two protection devices is feasible in a particular anatomy context. ..
  29. Hsu C, Chang L, Yu N. Estrogen suppression of preincubated tadpole ovaries in vitro by cyanoketone. Proc Natl Sci Counc Repub China B. 1988;12:84-7 pubmed
    ..However, a maximal inhibition effect of 95% was obtained at the dose of 0.1 microgram/ml. Therefore, the difference between non-preincubation of the previous experiments and preincubation of the present study does exist as we predicted. ..
  30. Martins V, Asad Y, Wilsher N, Raynaud F. A validated liquid chromatographic-tandem mass spectroscopy method for the quantification of abiraterone acetate and abiraterone in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2006;843:262-7 pubmed
    ..9% for both analytes. This method will be applied to a clinical trial investigating the pharmacokinetics of abiraterone acetate and abiraterone in patients with prostate cancer. ..
  31. Grzegorzewski W. The influence of male pheromones on the contractile reactivity of the isolated superficial veins of the nose and face during the estrous cycle in gilts. Pol J Vet Sci. 2005;8:57-64 pubmed
  32. Badrising S, van der Noort V, van Oort I, van den Berg H, Los M, Hamberg P, et al. Clinical activity and tolerability of enzalutamide (MDV3100) in patients with metastatic, castration-resistant prostate cancer who progress after docetaxel and abiraterone treatment. Cancer. 2014;120:968-75 pubmed publisher
    ..Enz has modest clinical activity in patients with metastatic, castrate-resistant prostate cancer who previously received Doc and AA. PSA response to Doc and AA does not predict for PSA response to ENz. ..
  33. Frye C, Bayon L, Pursnani N, Purdy R. The neurosteroids, progesterone and 3alpha,5alpha-THP, enhance sexual motivation, receptivity, and proceptivity in female rats. Brain Res. 1998;808:72-83 pubmed
    ..These studies suggest that P and 3alpha,5alpha-THP may have some common effects on reproductive behavior, e.g., sexual motivation, receptivity, and proceptivity. ..
  34. Redding M, Surati M. Emerging treatments for castrate-resistant prostate cancer. J Pharm Pract. 2011;24:366-73 pubmed publisher
    ..The results of ongoing studies with these new treatment agents may offer viable alternatives to the traditional treatment of CRPC to decrease disease progression and improve overall survival. ..
  35. Pal S, Twardowski P, Josephson D. Beyond castration and chemotherapy: novel approaches to targeting androgen-driven pathways. Maturitas. 2009;64:61-6 pubmed publisher
    ..On the basis of these compelling data, both abiraterone and MDV3100 will be examined in the phase III setting. ..
  36. Turitto G, Di Bisceglie M, Moraca L, Sasso N, Sepede C, Suriano A, et al. [Abiraterone acetate: a novel therapeutic option in hormone-refractory prostate cancer]. Recenti Prog Med. 2012;103:74-8 pubmed publisher
  37. Sobolevsky T, Rodchenkov G. Mass spectrometric description of novel oxymetholone and desoxymethyltestosterone metabolites identified in human urine and their importance for doping control. Drug Test Anal. 2012;4:682-91 pubmed publisher
    ..These novel metabolites could be detected using GC-MS/MS at least for 14 days after administration of these anabolic steroids compared to 5-7 days for previously reported metabolites. ..
  38. De Matteo R, Blasch N, Stokes V, Davis P, Harding R. Induced preterm birth in sheep: a suitable model for studying the developmental effects of moderately preterm birth. Reprod Sci. 2010;17:724-33 pubmed publisher
    ..We conclude that moderately preterm birth in sheep is characterized by a greater survival of female lambs than males and has significant effects on organ development. ..
  39. Treyer V, Koch H, Briner H, Jones N, Buck A, Simmen D. Male subjects who could not perceive the pheromone 5a-androst-16-en-3-one, produced similar orbitofrontal changes on PET compared with perceptible phenylethyl alcohol (rose). Rhinology. 2006;44:278-82 pubmed
    ..The same regions were activated when the subjects smelled a rose-like odour. This study shows that a pheromone, which is not consciously detected, can evoke a response in the brain that is similar to a detectable odour. ..
  40. Thamotharan S, Parthasarathi V, Gupta R, Jindal D, Linden A. 2'-(4-Fluorophenyl)-[1,2,3]triazolo[4',5':16,17]androst-5-en-3beta-ol methanol hemisolvate. Acta Crystallogr C. 2004;60:o405-7 pubmed
    ..O-H.O-H pattern. Intermolecular C-H.O and C-H.F interactions are also observed. ..
  41. Soucy P, Lacoste L, Luu The V. Assessment of porcine and human 16-ene-synthase, a third activity of P450c17, in the formation of an androstenol precursor. Role of recombinant cytochrome b5 and P450 reductase. Eur J Biochem. 2003;270:1349-55 pubmed
    ..Our results therefore demonstrate that human P450c17, as other enzymes of the classical steroidogenic pathway, is involved in the biosynthetic pathway leading to the formation of androstenol. ..
  42. Habeeb A, Praveen Rao P, Knaus E. Design and synthesis of 4,5-diphenyl-4-isoxazolines: novel inhibitors of cyclooxygenase-2 with analgesic and antiinflammatory activity. J Med Chem. 2001;44:2921-7 pubmed
    ..46 A inside the entrance to the COX-2 secondary pocket (Val(523)) and that a C-3 Me (13j, 13k) central isoxazoline ring substituent is crucial to selective inhibition of COX-2 for this class of compounds. ..
  43. Stefanczyk Krzymowska S, Krzymowski T, Grzegorzewski W, W sowska B, Skipor J. Humoral pathway for local transfer of the priming pheromone androstenol from the nasal cavity to the brain and hypophysis in anaesthetized gilts. Exp Physiol. 2000;85:801-9 pubmed
  44. Fizazi K, Flaig T, Stöckle M, Scher H, de Bono J, Rathkopf D, et al. Does Gleason score at initial diagnosis predict efficacy of abiraterone acetate therapy in patients with metastatic castration-resistant prostate cancer? An analysis of abiraterone acetate phase III trials. Ann Oncol. 2016;27:699-705 pubmed publisher
    ..cou-aa-301 (nct00638690); cou-aa-302 (nct00887198). ..
  45. Bruno R, Vasaitis T, Gediya L, Purushottamachar P, Godbole A, Ates Alagoz Z, et al. Synthesis and biological evaluations of putative metabolically stable analogs of VN/124-1 (TOK-001): head to head anti-tumor efficacy evaluation of VN/124-1 (TOK-001) and abiraterone in LAPC-4 human prostate cancer xenograft model. Steroids. 2011;76:1268-79 pubmed publisher
    ..These studies further demonstrate the efficacy of 5 in a clinically relevant prostate cancer model and justify its current clinical development as a potential treatment of prostate cancer. ..
  46. Antonarakis E, Eisenberger M. Expanding treatment options for metastatic prostate cancer. N Engl J Med. 2011;364:2055-8 pubmed publisher
  47. Frese S, Velders M, Schleipen B, Schanzer W, Bloch W, Diel P. Myosin heavy chain expression pattern as a marker for anabolic potency: desoxymethyltestosterone (madol), norandrostenedione and testosterone repress MHC-IIb expression and stimulate MHC-IId/x expression in orchiectomized rat gastrocnemius muscle. Arch Toxicol. 2011;85:635-43 pubmed publisher
    ..The molecular mechanisms as well as the androgen-dependent regulation of MHC expression in intact skeletal muscle remain to be further investigated. ..
  48. Weusten J, van der Wouw M, Smals A, Hofman J, Kloppenborg P, Benraad T. Differential metabolism of pregnenolone by testicular homogenates of humans and two species of macaques. Lack of synthesis of the human sex pheromone precursor 5,16-androstadien-3 beta-ol in nonhuman primates. Horm Metab Res. 1990;22:619-21 pubmed
    ..So far, man and boar are the only species harbouring delta 16-synthetase activity in their testes. These in vitro data indicate that the nonhuman primates studied are not suitable models for the study of human testicular function. ..
  49. Richards J, Lim A, Hay C, Taylor A, Wingate A, Nowakowska K, et al. Interactions of abiraterone, eplerenone, and prednisolone with wild-type and mutant androgen receptor: a rationale for increasing abiraterone exposure or combining with MDV3100. Cancer Res. 2012;72:2176-82 pubmed publisher
    ..Together, our findings provide a strong rationale for clinical evaluation of combined CYP17A1 inhibition and AR antagonism. ..
  50. Kim W, Ryan C. Androgen receptor directed therapies in castration-resistant metastatic prostate cancer. Curr Treat Options Oncol. 2012;13:189-200 pubmed publisher
    ..In this review, the rationale for and clinical results with these new therapies will be discussed as will the future directions required to fully leverage these therapeutic modalities to the maximum clinical benefit for patients. ..
  51. Loria R. Immune up-regulation and tumor apoptosis by androstene steroids. Steroids. 2002;67:953-66 pubmed
    ..Following host injury, the balance between the epimers and isomers is a determining factor in the overall regulation of hematopoiesis, TH(l)/TH(2) balance, and host resistance to infections and tumor growth. ..
  52. Kraemer R, Acevedo E, Synovitz L, Hebert E, Gimpel T, Castracane V. Leptin and steroid hormone responses to exercise in adolescent female runners over a 7-week season. Eur J Appl Physiol. 2001;86:85-91 pubmed
    ..Data also suggest that training and/or maturation increases resting testosterone concentrations and testosterone responses to running in adolescent female runners during a training season. ..
  53. Taplin M, Berry W, Casey A, Aslo A. A urologic oncology roundtable discussion: issues to consider in choosing treatment for metastatic castration-resistant prostate cancer. Hosp Pract (1995). 2013;41:81-2 pubmed publisher