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Chemical Compound Review

Raffolutil     (2S)-N-[4-cyano-3- (trifluoromethyl)phenyl]...

Synonyms: bicalutamida, bicalutamidum, R-BICALUTAMIDE, CHEMBL409, SureCN3612, ...
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Disease relevance of Casodex


Psychiatry related information on Casodex


High impact information on Casodex

  • The antiandrogen Casodex and specific inhibitors of Src and PI3-kinase prevent both hormonal effects, DNA synthesis and cytoskeletal changes [6].
  • We solved the x-ray crystal structure of the mutant W741L AR ligand-binding domain bound to R-bicalutamide at 1.8-A resolution [7].
  • The antiandrogen Casodex blocked the effect of androgen, implicating the androgen receptor in regulation of ABCA1 expression by androgens [8].
  • In contrast, transcription through the PSA P/E promoter, a prototypical AR-dependent promoter directly activated by agonist, was obliterated only by Casodex [9].
  • We show that expression of RasN17 in the hormone-refractory C4-2 cell line enhances in vitro sensitivity to the growth-inhibitory action of the antiandrogen Casodex and inhibits anchorage-independent cell growth [10].

Chemical compound and disease context of Casodex


Biological context of Casodex


Anatomical context of Casodex


Associations of Casodex with other chemical compounds


Gene context of Casodex

  • Like Cdc6, the levels of both cyclins A and B were attenuated in Casodex-treated cells [17].
  • The anti-androgen Casodex enhances the growth-inhibitory action of PTEN and this effect is independent of Akt phosphorylation [25].
  • RT-PCR based analysis demonstrates that in LNCaP cells Casodex coordinately alters the expression of steady-state level of mRNAs of several matrix metalloproteases and their cognate inhibitors (most notably MMP2 and TIMP1) [26].
  • We detect binding of SMRT to hAR when treating with the antiandrogen CPA, but not with the antihormones casodex or hydroxyflutamide [27].
  • The anti-androgen Casodex reduced 5alpha-DHT-stimulated cell growth but had no effect on EGF-R mediated LNCaP growth or EGF-stimulated activated MAPK activity [28].

Analytical, diagnostic and therapeutic context of Casodex

  • Chemoprevention of rat prostate carcinogenesis by use of finasteride or casodex [29].
  • In a comparative trial, bicalutamide (Casodex) was more effective than flutamide (each in combination with an LHRH analogue) in terms of time to treatment failure and produced a significantly lower incidence of diarrhoea [30].
  • Bicalutamide (Casodex) 150 mg/day was administered for 12 months from the day of radiotherapy [31].
  • The peripheral selectivity of Casodex in the intact male rat was related to the distribution of radiolabelled antiandrogen following intravenous injection [18].
  • METHODS: A total of 1,453 patients with either confirmed metastatic disease (M1), or T3/T4 non-metastatic disease with elevated prostate-specific antigen (M0) were recruited into one of two identical, multicentre, randomised studies to compare 'Casodex' 150 mg/day with castration [32].


  1. Antiandrogen-induced cell death in LNCaP human prostate cancer cells. Lee, E.C., Zhan, P., Schallhom, R., Packman, K., Tenniswood, M. Cell Death Differ. (2003) [Pubmed]
  2. Re: A prospective, placebo-controlled study of the antiandrogen Casodex as treatment for patients with benign prostatic hyperplasia. Strutt, K.L., Blackledge, G.R., Kennealey, G.T. J. Urol. (1994) [Pubmed]
  3. A prospective, placebo-controlled study of the antiandrogen Casodex as treatment for patients with benign prostatic hyperplasia. Eri, L.M., Tveter, K.J. J. Urol. (1993) [Pubmed]
  4. Antiproliferative activity of casodex (ICI 176.334) in hormone-dependent tumours. Maucher, A., von Angerer, E. J. Cancer Res. Clin. Oncol. (1993) [Pubmed]
  5. Effects of the nonsteroidal antiandrogen Casodex on lipoproteins, fibrinogen and plasminogen activator inhibitor in patients with benign prostatic hyperplasia. Eri, L.M., Urdal, P. Eur. Urol. (1995) [Pubmed]
  6. 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]
  7. Structural basis for antagonism and resistance of bicalutamide in prostate cancer. Bohl, C.E., Gao, W., Miller, D.D., Bell, C.E., Dalton, J.T. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  8. Androgenic suppression of ATP-binding cassette transporter A1 expression in LNCaP human prostate cancer cells. Fukuchi, J., Hiipakka, R.A., Kokontis, J.M., Hsu, S., Ko, A.L., Fitzgerald, M.L., Liao, S. Cancer Res. (2004) [Pubmed]
  9. Changes in androgen receptor nongenotropic signaling correlate with transition of LNCaP cells to androgen independence. Unni, E., Sun, S., Nan, B., McPhaul, M.J., Cheskis, B., Mancini, M.A., Marcelli, M. Cancer Res. (2004) [Pubmed]
  10. Attenuation of Ras signaling restores androgen sensitivity to hormone-refractory C4-2 prostate cancer cells. Bakin, R.E., Gioeli, D., Bissonette, E.A., Weber, M.J. Cancer Res. (2003) [Pubmed]
  11. Androgen receptor antagonists (antiandrogens): structure-activity relationships. Singh, S.M., Gauthier, S., Labrie, F. Current medicinal chemistry. (2000) [Pubmed]
  12. Bicalutamide 150mg: a review of its use in the treatment of locally advanced prostate cancer. Wellington, K., Keam, S.J. Drugs (2006) [Pubmed]
  13. Effect of antiandrogens casodex and epitestosterone on bone composition in mice. Broulik, P.D., Stárka, L. Bone (1997) [Pubmed]
  14. A controlled trial of Casodex (bicalutamide) vs. flutamide, each in combination with luteinising hormone-releasing hormone analogue therapy in patients with advanced prostate cancer. Casodex Combination Study Group. Soloway, M.S., Schellhammer, P., Sharifi, R., Venner, P., Patterson, A.L., Sarosdy, M., Vogelzang, N., Jones, J., Kolvenbag, G. Eur. Urol. (1996) [Pubmed]
  15. A controlled trial of bicalutamide versus flutamide, each in combination with luteinizing hormone-releasing hormone analogue therapy, in patients with advanced prostate cancer. Casodex Combination Study Group. Schellhammer, P., Sharifi, R., Block, N., Soloway, M., Venner, P., Patterson, A.L., Sarosdy, M., Vogelzang, N., Jones, J., Kolvenbag, G. Urology (1995) [Pubmed]
  16. Structural basis for accommodation of nonsteroidal ligands in the androgen receptor. Bohl, C.E., Miller, D.D., Chen, J., Bell, C.E., Dalton, J.T. J. Biol. Chem. (2005) [Pubmed]
  17. Androgen receptor regulates Cdc6 in synchronized LNCaP cells progressing from G1 to S phase. Bai, V.U., Cifuentes, E., Menon, M., Barrack, E.R., Reddy, G.P. J. Cell. Physiol. (2005) [Pubmed]
  18. A possible explanation for the peripheral selectivity of a novel non-steroidal pure antiandrogen, Casodex (ICI 176,334). Freeman, S.N., Mainwaring, W.I., Furr, B.J. Br. J. Cancer (1989) [Pubmed]
  19. Androgen receptor localisation and turnover in human prostate epithelium treated with the antiandrogen, casodex. Waller, A.S., Sharrard, R.M., Berthon, P., Maitland, N.J. J. Mol. Endocrinol. (2000) [Pubmed]
  20. Endocrine profiles during administration of the new non-steroidal anti-androgen Casodex in prostate cancer. Verhelst, J., Denis, L., Van Vliet, P., Van Poppel, H., Braeckman, J., Van Cangh, P., Mattelaer, J., D'Hulster, D., Mahler, C. Clin. Endocrinol. (Oxf) (1994) [Pubmed]
  21. Identification of human male germ cell-associated kinase, a kinase transcriptionally activated by androgen in prostate cancer cells. Xia, L., Robinson, D., Ma, A.H., Chen, H.C., Wu, F., Qiu, Y., Kung, H.J. J. Biol. Chem. (2002) [Pubmed]
  22. Liganded androgen receptor interaction with beta-catenin: nuclear co-localization and modulation of transcriptional activity in neuronal cells. Pawlowski, J.E., Ertel, J.R., Allen, M.P., Xu, M., Butler, C., Wilson, E.M., Wierman, M.E. J. Biol. Chem. (2002) [Pubmed]
  23. Cross-talk between steroid-receptor-mediated and cell-membrane-receptor-mediated signalling pathways results in the in vivo modulation of c-Met and ornithine decarboxylase gene expression in mouse kidney. Dudkowska, M., Stachurska, A., Chmurzyska, W., Grzelakowska-Sztabert, B., Manteuffel-Cymborowska, M. Biochem. J. (2001) [Pubmed]
  24. Induction of androgen receptor by 1alpha,25-dihydroxyvitamin D3 and 9-cis retinoic acid in LNCaP human prostate cancer cells. Zhao, X.Y., Ly, L.H., Peehl, D.M., Feldman, D. Endocrinology (1999) [Pubmed]
  25. Conditional expression of PTEN alters the androgen responsiveness of prostate cancer cells. Wu, Z., Conaway, M., Gioeli, D., Weber, M.J., Theodorescu, D. Prostate (2006) [Pubmed]
  26. Induction of invasive phenotype by Casodex in hormone-sensitive prostate cancer cells. Zhan, P., Lee, E.C., Packman, K., Tenniswood, M. J. Steroid Biochem. Mol. Biol. (2002) [Pubmed]
  27. The amino terminus of the human AR is target for corepressor action and antihormone agonism. Dotzlaw, H., Moehren, U., Mink, S., Cato, A.C., Iñiguez Lluhí, J.A., Baniahmad, A. Mol. Endocrinol. (2002) [Pubmed]
  28. Effect of an EGF-R selective tyrosine kinase inhibitor and an anti-androgen on LNCaP cells: identification of divergent growth regulatory pathways. Jones, H.E., Barrow, D., Dutkowski, C.M., Goddard, L., Smith, C., Harper, M.E., Nicholson, R.I. Prostate (2001) [Pubmed]
  29. Chemoprevention of rat prostate carcinogenesis by use of finasteride or casodex. Tsukamoto, S., Akaza, H., Imada, S., Koiso, K., Shirai, T., Ideyama, Y., Kudo, M. J. Natl. Cancer Inst. (1995) [Pubmed]
  30. Commentary on maximal androgen blockade in prostate cancer: a theory to put into practice? Denis, L. Prostate (1995) [Pubmed]
  31. Prophylactic breast irradiation with a single dose of electron beam radiotherapy (10 Gy) significantly reduces the incidence of bicalutamide-induced gynecomastia. Tyrrell, C.J., Payne, H., Tammela, T.L., Bakke, A., Lodding, P., Goedhals, L., Van Erps, P., Boon, T., Van De Beek, C., Andersson, S.O., Morris, T., Carroll, K. Int. J. Radiat. Oncol. Biol. Phys. (2004) [Pubmed]
  32. A randomised comparison of 'Casodex' (bicalutamide) 150 mg monotherapy versus castration in the treatment of metastatic and locally advanced prostate cancer. Tyrrell, C.J., Kaisary, A.V., Iversen, P., Anderson, J.B., Baert, L., Tammela, T., Chamberlain, M., Webster, A., Blackledge, G. Eur. Urol. (1998) [Pubmed]
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