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Chemical Compound Review

Androstane     (5R,8S,9S,10S,13S,14S)-10,13- dimethyl-2,3...

Synonyms: AG-F-54619, A0887_SIGMA, CHEBI:28859, NSC-49000, AC1L3RLK, ...
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Disease relevance of Etioallocholane

  • Pseudomonas mutant strains that accumulate androstane and seco-androstane intermediates from bile acids [1].
  • The excretion rates of androstane and pregnane metabolites of patients with liver disease were far lower than those of healthy persons [2].
  • 9 alpha-Hydroxylation of delta 5-3 beta-hydroxysteroids (of androstane, pregnane, 24-nor- and 21,24-bisnorcholane groups) was carried out by a Rhodococcus sp., isolated from a petroleum-containing soil sample [3].
  • In single-dose murine toxicity evaluations, the androstane derivative was non-toxic at doses up to 400 mg/kg [4].
  • Steroidal quaternary ammonium compounds 12 and 13 with quaternised nitrogen at positions 3 and 16 of the steroidal nucleus in androstane series were synthesised and their neuromuscular blocking activities and ganglion blocking activities were studied using chick biventer and anaesthetised cat as the models [5].

High impact information on Etioallocholane

  • These androstane ligands are examples of naturally occurring inverse agonists that reverse transcriptional activation by nuclear receptors [6].
  • Immunoprecipitation experiments using the hsp90 antibody demonstrated the presence of PXR in a complex with the endogenous cytoplasmic constitutive active/androstane receptor retention protein (CCRP) in HepG2 cells [7].
  • Cellular protein binding of a number of androstene and androstane derivatives that promote the growth of the vagina in rats has been studied [8].
  • Conservation of signaling pathways of xenobiotic-sensing orphan nuclear receptors, chicken xenobiotic receptor, constitutive androstane receptor, and pregnane X receptor, from birds to humans [9].
  • Serine 202 regulates the nuclear translocation of constitutive active/androstane receptor [10].

Biological context of Etioallocholane


Anatomical context of Etioallocholane

  • The transbilayer movement and distribution of spin-labeled analogs of the steroids androstane (SLA) and cholestane (SLC) were investigated in the human erythrocyte and in liposomes [16].
  • Lack of response to androstane therapy may be related to lack of response by bone marrow monocyte macrophages or to the inability of granulopoietic cells to respond to the increased CSF production induced by androstane therapy [17].
  • Effects of the interaction of the ovary with an androstane nitrile on the uterus of the rat [18].
  • Nuclear receptors (NR), including retinoic acid and retinoid X receptors (RAR, RXR), pregnane X receptor (PXR), constitutive androstane receptor, and peroxisome proliferator-activated receptor (PPARalpha) modify the expression of other genes, such as cytochrome p450 enzymes (CYP), sulfotransferases (SULT), and UDP glucuronosyl transferases (UGT) [19].
  • Also the investigation of different androstane metabolites, i.e. etiocholanolone, should be pursued to determined if a more effective stimulus of stem cell proliferation can be achieved [20].

Associations of Etioallocholane with other chemical compounds

  • The constitutive active/androstane receptor regulates phenytoin induction of Cyp2c29 [21].
  • We propose that, in this evolutionarily ancient vertebrate, VDR may function in part, like pregnane X receptors and constitutive androstane receptors, to induce P450 enzymes for xenobiotic detoxification [22].
  • Carbon-13 nuclear magnetic resonance spectra for 31 3 beta-hydroxy and acetoxy androstane derivatives bearing vicinal oxygenated functions at ring D with and without oxygenated functions at C-6 are reported [23].
  • The latter modifications are likely to increase the specificity of androstane derivatives for receptors other than androgen binding proteins, such as the progesterone receptor [24].
  • Nandrolone decanoate (ND), an estrene derivative, but not stanozolol (ST), a derivative of the androstane series, up-regulated the levels of HSP72 and changed the proportions of various charge variants of the cytosolic HSP70s in sedentary and exercise-trained rats, exclusively in fast-twitch fibres [25].

Gene context of Etioallocholane

  • Two orphan nuclear receptors, constitutive active (or androstane) receptor (CAR) and pregnane X receptor (PXR), are among the most important mediators of ligand-activated transcriptional induction of liver microsomal cytochrome P450 drug-metabolizing enzymes [26].
  • Regulation of the human UGT1A1 gene by nuclear receptors constitutive active/androstane receptor, pregnane X receptor, and glucocorticoid receptor [15].
  • The relative binding affinity to the androgen receptor determined in competition assays showed that in the androstane series the fluoro steroids have the highest affinity and that F-17alpha-CH3-DHT (4) has a higher affinity than 5alpha-DHT [27].
  • The introduction of a 16-methyl substituent into 5alpha-androstane molecules substantially decreases the binding affinity to the androgen receptor and 16alpha-methyl derivatives were always bound more weakly than the 16beta-methyl isomers [28].
  • New D-modified androstane derivatives as aromatase inhibitors [29].

Analytical, diagnostic and therapeutic context of Etioallocholane


  1. Pseudomonas mutant strains that accumulate androstane and seco-androstane intermediates from bile acids. Leppik, R.A., Sinden, D.J. Biochem. J. (1987) [Pubmed]
  2. The identification of urinary bile alcohols by gas chromatography-mass spectrometry in patients with liver disease and in healthy individuals. Ludwig-Köhn, H., Henning, H.V., Sziedat, A., Matthaei, D., Spiteller, G., Reiner, J., Egger, H.J. Eur. J. Clin. Invest. (1983) [Pubmed]
  3. Synthesis of 9 alpha-hydroxysteroids by a Rhodococcus sp. Datcheva, V.K., Voishvillo, N.E., Kamernitskii, A.V., Vlahov, R.J., Reshetova, I.G. Steroids (1989) [Pubmed]
  4. Antimicrobial and cancer cell growth inhibitory activities of 3beta-acetoxy-17beta-(L-prolyl)amino-5alpha-androstane in vitro. Pettit, R.K., Cage, G.D., Pettit, G.R., Liebman, J.A. Int. J. Antimicrob. Agents (2000) [Pubmed]
  5. Synthesis and neuromuscular blocking activity of 16beta-N-methylpiperazino steroidal derivatives. Jindal, D.P., Piplani, P., Fajrak, H., Prior, C., Marshall, I.G. European journal of medicinal chemistry. (2002) [Pubmed]
  6. Androstane metabolites bind to and deactivate the nuclear receptor CAR-beta. Forman, B.M., Tzameli, I., Choi, H.S., Chen, J., Simha, D., Seol, W., Evans, R.M., Moore, D.D. Nature (1998) [Pubmed]
  7. Cytoplasmic localization of pregnane X receptor and ligand-dependent nuclear translocation in mouse liver. Squires, E.J., Sueyoshi, T., Negishi, M. J. Biol. Chem. (2004) [Pubmed]
  8. Selective retention and formation of a delta5-androstenediol-receptor complex in cell nuclei of the rat vagina. Shao, T.C., Castañeda, E., Rosenfield, R.L., Liao, S. J. Biol. Chem. (1975) [Pubmed]
  9. Conservation of signaling pathways of xenobiotic-sensing orphan nuclear receptors, chicken xenobiotic receptor, constitutive androstane receptor, and pregnane X receptor, from birds to humans. Handschin, C., Podvinec, M., Stöckli, J., Hoffmann, K., Meyer, U.A. Mol. Endocrinol. (2001) [Pubmed]
  10. Serine 202 regulates the nuclear translocation of constitutive active/androstane receptor. Hosseinpour, F., Moore, R., Negishi, M., Sueyoshi, T. Mol. Pharmacol. (2006) [Pubmed]
  11. Novel glucocorticoid antedrugs possessing a 17beta-(gamma-lactone) ring. Procopiou, P.A., Biggadike, K., English, A.F., Farrell, R.M., Hagger, G.N., Hancock, A.P., Haase, M.V., Irving, W.R., Sareen, M., Snowden, M.A., Solanke, Y.E., Tralau-Stewart, C.J., Walton, S.E., Wood, J.A. J. Med. Chem. (2001) [Pubmed]
  12. On the mechanism of erythropoietin-induced differentiation. XIV. The apparent effect of etiocholanolone on initiation of erythropoiesis. Gross, M., Goldwasser, E. Exp. Hematol. (1976) [Pubmed]
  13. Action of testosterone, dihydrotestosterone and 5alpha androstane 3alpha, 17beta diol on the spermatogenesis of immature rats. Chemes, H.E., Podesta, E., Rivarola, M.A. Biol. Reprod. (1976) [Pubmed]
  14. In vitro and in vivo activity of 16,17-dehydro-epipregnanolones: 17,20-bond torsional energy analysis and D-ring conformation. Bolger, M.B., Wieland, S., Hawkinson, J.E., Xia, H., Upasani, R., Lan, N.C. Pharm. Res. (1996) [Pubmed]
  15. Regulation of the human UGT1A1 gene by nuclear receptors constitutive active/androstane receptor, pregnane X receptor, and glucocorticoid receptor. Sugatani, J., Sueyoshi, T., Negishi, M., Miwa, M. Meth. Enzymol. (2005) [Pubmed]
  16. Rapid transbilayer movement of spin-labeled steroids in human erythrocytes and in liposomes. Müller, P., Herrmann, A. Biophys. J. (2002) [Pubmed]
  17. The effect of androstanes on granulopoiesis in vitro and in vivo. Francis, G.E., Berney, J.J., Bateman, S.M., Hoffbrand, A.V. Br. J. Haematol. (1977) [Pubmed]
  18. Effects of the interaction of the ovary with an androstane nitrile on the uterus of the rat. Bennett, D.R., Debono, M., Powell, J.G., Rathmacher, R.P., Cochrane, R.L. J. Endocrinol. Invest. (1982) [Pubmed]
  19. Expression of nuclear receptor and target genes in liver and intestine of neonatal calves fed colostrum and vitamin A. Krüger, K.A., Blum, J.W., Greger, D.L. J. Dairy Sci. (2005) [Pubmed]
  20. Anabolic steroids in aplastic anemia. Gardner, F.H. Acta endocrinologica. Supplementum. (1985) [Pubmed]
  21. The constitutive active/androstane receptor regulates phenytoin induction of Cyp2c29. Jackson, J.P., Ferguson, S.S., Moore, R., Negishi, M., Goldstein, J.A. Mol. Pharmacol. (2004) [Pubmed]
  22. Cloning of a functional vitamin D receptor from the lamprey (Petromyzon marinus), an ancient vertebrate lacking a calcified skeleton and teeth. Whitfield, G.K., Dang, H.T., Schluter, S.F., Bernstein, R.M., Bunag, T., Manzon, L.A., Hsieh, G., Dominguez, C.E., Youson, J.H., Haussler, M.R., Marchalonis, J.J. Endocrinology (2003) [Pubmed]
  23. Carbon-13 nuclear magnetic resonance spectral data of steroidal vicinal ketols and related compounds. Doller, D., Gros, E.G. Steroids (1991) [Pubmed]
  24. Interaction of A-nor, A, 19-dinor, and A-homo-5 alpha-androstane derivatives with the androgen receptor and the epididymal androgen-binding protein. Russeau, G.G., Quivy, J.I. Steroids (1981) [Pubmed]
  25. Anabolic steroid and gender-dependent modulation of cytosolic HSP70s in fast- and slow-twitch skeletal muscle. González, B., Hernando, R., Manso, R. J. Steroid Biochem. Mol. Biol. (2000) [Pubmed]
  26. Insights from a three-dimensional model into ligand binding to constitutive active receptor. Xiao, L., Cui, X., Madison, V., White, R.E., Cheng, K.C. Drug Metab. Dispos. (2002) [Pubmed]
  27. 7alpha-Iodo and 7alpha-fluoro steroids as androgen receptor-mediated imaging agents. Labaree, D.C., Hoyte, R.M., Nazareth, L.V., Weigel, N.L., Hochberg, R.B. J. Med. Chem. (1999) [Pubmed]
  28. Configurational analysis and relative binding affinities of 16-methyl-5alpha-androstane derivatives. Tapolcsányi, P., Wölfling, J., Tóth, I., Szécsi, M., Forgó, P., Schneider, G. Steroids (2001) [Pubmed]
  29. New D-modified androstane derivatives as aromatase inhibitors. Penov Gasi, K.M., Stanković, S.M., Csanádi, J.J., Djurendić, E.A., Sakac, M.N., Medić Mijacević, L., Arcson, O.N., Stojanović, S.Z., Andrić, S., Molnar Gabor, D., Kovacević, R. Steroids (2001) [Pubmed]
  30. Analysis of some steroids by thin-layer chromatography using optimum mobile phases. Cimpoiu, C., Hosu, A., Hodisan, S. Journal of pharmaceutical and biomedical analysis. (2006) [Pubmed]
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