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Chemical Compound Review

METRIBOLONE     (8S,13R,14S,17S)-17-hydroxy- 13,17-dimethyl...

Synonyms: Metribolona, Metribolonum, CHEMBL166444, SureCN114862, R-1881, ...
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Disease relevance of R 1881


High impact information on R 1881


Chemical compound and disease context of R 1881


Biological context of R 1881


Anatomical context of R 1881


Associations of R 1881 with other chemical compounds


Gene context of R 1881

  • Insulin-like growth factor-I (IGF-I), at a concentration of 50 ng/ml, stimulated AR-mediated reporter gene transcription to the same extent as the synthetic androgen methyltrienolone [25].
  • Real-time PCR showed a significant increase in NAT1 mRNA levels for R1881-treated cells (6.60 +/- 0.80) compared with vehicle-treated controls (1.53 +/- 0.17), which was not due to a change in mRNA stability [16].
  • Growth of hormone-dependent LNCaP cells in hormone-depleted media led to increased WNT11 expression, which was repressed by the synthetic androgen R1881 [26].
  • Induction of cyclin A1 expression in LNCaP cells led to an increase in VEGF expression and this effect was manifested upon the R1881 treatment [27].
  • In MDA-MB-453 cells, which express the AR but not the ER or PR, DHT and R1881 increased PRLR binding to 150% of control values at 0.1 nM [28].

Analytical, diagnostic and therapeutic context of R 1881


  1. AIbZIP, a novel bZIP gene located on chromosome 1q21.3 that is highly expressed in prostate tumors and of which the expression is up-regulated by androgens in LNCaP human prostate cancer cells. Qi, H., Fillion, C., Labrie, Y., Grenier, J., Fournier, A., Berger, L., El-Alfy, M., Labrie, C. Cancer Res. (2002) [Pubmed]
  2. Inhibition of endometrial carcinoma cell cultures by a synthetic androgen. Centola, G.M. Cancer Res. (1985) [Pubmed]
  3. Hypoxia increases androgen receptor activity in prostate cancer cells. Park, S.Y., Kim, Y.J., Gao, A.C., Mohler, J.L., Onate, S.A., Hidalgo, A.A., Ip, C., Park, E.M., Yoon, S.Y., Park, Y.M. Cancer Res. (2006) [Pubmed]
  4. Glucocorticoid and androgen activation of monoamine oxidase A is regulated differently by R1 and Sp1. Ou, X.M., Chen, K., Shih, J.C. J. Biol. Chem. (2006) [Pubmed]
  5. Progestin binding in testes from three siblings with the syndrome of male pseudohermaphroditism with testicular feminization. Dube, J.Y., Chapdelaine, P., Dionne, F.T., Cloutier, D., Tremblay, R.R. J. Clin. Endocrinol. Metab. (1978) [Pubmed]
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  7. Prooxidant-antioxidant shift induced by androgen treatment of human prostate carcinoma cells. Ripple, M.O., Henry, W.F., Rago, R.P., Wilding, G. J. Natl. Cancer Inst. (1997) [Pubmed]
  8. Reduced affinity of the androgen receptor for 5 alpha-dihydrotestosterone but not methyltrienolone in a form of partial androgen resistance. Studies on cultured genital skin fibroblasts. Pinsky, L., Kaufman, M., Chudley, A.E. J. Clin. Invest. (1985) [Pubmed]
  9. Androgen-stimulated DNA synthesis and cytoskeletal changes in fibroblasts by a nontranscriptional receptor action. Castoria, G., Lombardi, M., Barone, M.V., Bilancio, A., Di Domenico, M., Bottero, D., Vitale, F., Migliaccio, A., Auricchio, F. J. Cell Biol. (2003) [Pubmed]
  10. The androgen receptor represses transforming growth factor-beta signaling through interaction with Smad3. Chipuk, J.E., Cornelius, S.C., Pultz, N.J., Jorgensen, J.S., Bonham, M.J., Kim, S.J., Danielpour, D. J. Biol. Chem. (2002) [Pubmed]
  11. Antiandrogen effects of mifepristone on coactivator and corepressor interactions with the androgen receptor. Song, L.N., Coghlan, M., Gelmann, E.P. Mol. Endocrinol. (2004) [Pubmed]
  12. The androgen receptor T877A mutant recruits LXXLL and FXXLF peptides differently than wild-type androgen receptor in a time-resolved fluorescence resonance energy transfer assay. Ozers, M.S., Marks, B.D., Gowda, K., Kupcho, K.R., Ervin, K.M., De Rosier, T., Qadir, N., Eliason, H.C., Riddle, S.M., Shekhani, M.S. Biochemistry (2007) [Pubmed]
  13. Steroid hormone regulation of prostatic acid phosphatase expression in cultured human prostatic carcinoma cells. Schulz, P., Bauer, H.W., Fittler, F. Biol. Chem. Hoppe-Seyler (1985) [Pubmed]
  14. High affinity protein-binding and enzyme-inducing activity of methyltrienolone in Pseudomonas testosteroni. Pousette, A., Carlström, K. Acta Chem. Scand., B, Org. Chem. Biochem. (1986) [Pubmed]
  15. Interleukin-6 regulates prostate-specific protein expression in prostate carcinoma cells by activation of the androgen receptor. Hobisch, A., Eder, I.E., Putz, T., Horninger, W., Bartsch, G., Klocker, H., Culig, Z. Cancer Res. (1998) [Pubmed]
  16. Induction of human arylamine N-acetyltransferase type I by androgens in human prostate cancer cells. Butcher, N.J., Tetlow, N.L., Cheung, C., Broadhurst, G.M., Minchin, R.F. Cancer Res. (2007) [Pubmed]
  17. Low-calcium serum-free defined medium selects for growth of normal prostatic epithelial stem cells. Litvinov, I.V., Vander Griend, D.J., Xu, Y., Antony, L., Dalrymple, S.L., Isaacs, J.T. Cancer Res. (2006) [Pubmed]
  18. Androgens regulate protein kinase Cdelta transcription and modulate its apoptotic function in prostate cancer cells. Gavrielides, M.V., Gonzalez-Guerrico, A.M., Riobo, N.A., Kazanietz, M.G. Cancer Res. (2006) [Pubmed]
  19. Androgen receptor levels in cranial nerve nuclei and tongue muscles in rats. Yu, W.H., McGinnis, M.Y. J. Neurosci. (1986) [Pubmed]
  20. Selective modulation of genomic and nongenomic androgen responses by androgen receptor ligands. Lutz, L.B., Jamnongjit, M., Yang, W.H., Jahani, D., Gill, A., Hammes, S.R. Mol. Endocrinol. (2003) [Pubmed]
  21. Functional analysis of a novel androgen receptor mutation, Q902K, in an individual with partial androgen insensitivity. Umar, A., Berrevoets, C.A., Van, N.M., van Leeuwen, M., Verbiest, M., Kleijer, W.J., Dooijes, D., Grootegoed, J.A., Drop, S.L., Brinkmann, A.O. J. Clin. Endocrinol. Metab. (2005) [Pubmed]
  22. Alteration in gamma-glutamyl transpeptidase activity and messenger RNA of human prostate carcinoma cells by androgen. Ripple, M.O., Pickhardt, P.A., Wilding, G. Cancer Res. (1997) [Pubmed]
  23. Cell-specific regulation of androgen receptor phosphorylation in vivo. Taneja, S.S., Ha, S., Swenson, N.K., Huang, H.Y., Lee, P., Melamed, J., Shapiro, E., Garabedian, M.J., Logan, S.K. J. Biol. Chem. (2005) [Pubmed]
  24. Hsp90 regulates androgen receptor hormone binding affinity in vivo. Fang, Y., Fliss, A.E., Robins, D.M., Caplan, A.J. J. Biol. Chem. (1996) [Pubmed]
  25. Androgen receptor activation in prostatic tumor cell lines by insulin-like growth factor-I, keratinocyte growth factor, and epidermal growth factor. Culig, Z., Hobisch, A., Cronauer, M.V., Radmayr, C., Trapman, J., Hittmair, A., Bartsch, G., Klocker, H. Cancer Res. (1994) [Pubmed]
  26. Analysis of Wnt gene expression in prostate cancer: mutual inhibition by WNT11 and the androgen receptor. Zhu, H., Mazor, M., Kawano, Y., Walker, M.M., Leung, H.Y., Armstrong, K., Waxman, J., Kypta, R.M. Cancer Res. (2004) [Pubmed]
  27. A role for cyclin A1 in mediating the autocrine expression of vascular endothelial growth factor in prostate cancer. Wegiel, B., Bjartell, A., Ekberg, J., Gadaleanu, V., Brunhoff, C., Persson, J.L. Oncogene (2005) [Pubmed]
  28. Androgen regulation of prolactin-receptor gene expression in MCF-7 and MDA-MB-453 human breast cancer cells. Ormandy, C.J., Clarke, C.L., Kelly, P.A., Sutherland, R.L. Int. J. Cancer (1992) [Pubmed]
  29. Alteration of glyceraldehyde-3-phosphate dehydrogenase activity and messenger RNA content by androgen in human prostate carcinoma cells. Ripple, M.O., Wilding, G. Cancer Res. (1995) [Pubmed]
  30. Hormonal regulation of levels of the messenger RNA encoding hepatic P450 2c (IIC11), a constitutive male-specific form of cytochrome P450. Janeczko, R., Waxman, D.J., Le Blanc, G.A., Morville, A., Adesnik, M. Mol. Endocrinol. (1990) [Pubmed]
  31. Receptor-interacting protein 140 is a repressor of the androgen receptor activity. Carascossa, S., Gobinet, J., Georget, V., Lucas, A., Badia, E., Castet, A., White, R., Nicolas, J.C., Cavaillès, V., Jalaguier, S. Mol. Endocrinol. (2006) [Pubmed]
  32. Mosaicism due to a somatic mutation of the androgen receptor gene determines phenotype in androgen insensitivity syndrome. Holterhus, P.M., Brüggenwirth, H.T., Hiort, O., Kleinkauf-Houcken, A., Kruse, K., Sinnecker, G.H., Brinkmann, A.O. J. Clin. Endocrinol. Metab. (1997) [Pubmed]
  33. Androgens regulate the immune/inflammatory response and cell survival pathways in rat ventral prostate epithelial cells. Asirvatham, A.J., Schmidt, M., Gao, B., Chaudhary, J. Endocrinology (2006) [Pubmed]
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