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Chemical Compound Review

OH-flutamide     2-hydroxy-2-methyl-N-[4- nitro-3...

Synonyms: CHEMBL491, PubChem19862, S2174_Selleck, cc-376, AG-F-80421, ...
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Disease relevance of C14204


Psychiatry related information on C14204


High impact information on C14204


Chemical compound and disease context of C14204


Biological context of C14204


Anatomical context of C14204

  • The anti-androgen hydroxyflutamide and androgens inhibit interleukin-6 production by an androgen-responsive human osteoblastic cell line [20].
  • Finally, we demonstrated that hydroxyflutamide treatment of hFOB/AR-6 cells markedly inhibited the activation and binding of NF-kappaB (a known stimulator of IL-6 gene transcription) to its response element, thus providing a potential mechanism for its effect on IL-6 production by osteoblasts [20].
  • After i.p. injection of hCG at 1600 h on Day 0, 92% of hydroxyflutamide-treated rats ovulated a mean of 8.3 +/- 1.2 oocytes compared to 100% of controls, which ovulated 7.3 +/- 0.4 oocytes per rat: these groups were not significantly different from each other, nor from control rats that received no hCG [21].
  • Of surprise was the finding of an average DHT/HF index in 5 different nonprostate tissues, including breast, uterus, colon, kidney, and thyroid, that was similar to the index found in prostates [22].
  • In addition, the nonsteroidal antiandrogen hydroxyflutamide (HO-F) does not influence primary epithelial cell proliferation in this concentration range [23].

Associations of C14204 with other chemical compounds


Gene context of C14204


Analytical, diagnostic and therapeutic context of C14204

  • In two sublines of LNCaP cells that contain the mutated AR 877 thr-->ala and overexpressed CBP, increase in AR activity was observed after treatment with hydroxyflutamide but not with bicalutamide [12].
  • The antisteroidal compounds, mifepristone (RU486) and hydroxyflutamide, were also found to inhibit specifically the P4- and DHT-mediated increase in ADAMTS-1 mRNA and protein expression levels in these primary cell cultures in a concentration-dependent manner, respectively [32].
  • Muscle weights were also compared in animals receiving bilateral denervation of the BC/LA at the time of T and hFl capsule implantation and gonadectomy; local testosterone treatment failed to affect BC/LA weights in these denervated muscles [33].
  • Just before the last dose and 15 times during the subsequent 24 h, blood samples were obtained for the determination of plasma hydroxyflutamide (the active metabolite of flutamide) levels by high-performance liquid chromatography [34].
  • To test maintenance of copulatory behavior, T-filled capsules were implanted at the time of castration and rats received daily injections of either 0, 1, 5, 15 or 30 mg Sch 16423 [6].


  1. Vitamin E succinate inhibits the function of androgen receptor and the expression of prostate-specific antigen in prostate cancer cells. Zhang, Y., Ni, J., Messing, E.M., Chang, E., Yang, C.R., Yeh, S. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  2. Comparison of the pharmacological effects of a novel selective androgen receptor modulator, the 5alpha-reductase inhibitor finasteride, and the antiandrogen hydroxyflutamide in intact rats: new approach for benign prostate hyperplasia. Gao, W., Kearbey, J.D., Nair, V.A., Chung, K., Parlow, A.F., Miller, D.D., Dalton, J.T. Endocrinology (2004) [Pubmed]
  3. Inhibitory effect of hydroxyflutamide plus tamoxifen on oestradiol-induced growth of MCF-7 breast cancer cells. Di Monaco, M., Brignardello, E., Leonardi, L., Gatto, V., Boccuzzi, G. J. Cancer Res. Clin. Oncol. (1995) [Pubmed]
  4. Effects of short-term exposure to hydroxyflutamide in utero on the development of the reproductive tract in male mice. Silversides, D.W., Price, C.A., Cooke, G.M. Can. J. Physiol. Pharmacol. (1995) [Pubmed]
  5. Proteasome inhibitors and their combination with antiandrogens: effects on apoptosis, cellular proliferation and viability of prostatic adenocarcinoma cell cultures. Zwergel, T., Tahmatzopoulos, A., Wullich, B., Zwergel, U., Stöckle, M., Unteregger, G. Prostate Cancer Prostatic Dis. (2004) [Pubmed]
  6. Inhibition of cell nuclear androgen receptor binding and copulation in male rats by an antiandrogen, Sch 16423. McGinnis, M.Y., Mirth, M.C. Neuroendocrinology (1986) [Pubmed]
  7. The structural basis of androgen receptor activation: intramolecular and intermolecular amino-carboxy interactions. Schaufele, F., Carbonell, X., Guerbadot, M., Borngraeber, S., Chapman, M.S., Ma, A.A., Miner, J.N., Diamond, M.I. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  8. From HER2/Neu signal cascade to androgen receptor and its coactivators: a novel pathway by induction of androgen target genes through MAP kinase in prostate cancer cells. Yeh, S., Lin, H.K., Kang, H.Y., Thin, T.H., Lin, M.F., Chang, C. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  9. Testosterone increases thromboxane A2 receptors in cultured rat aortic smooth muscle cells. Masuda, A., Mathur, R., Halushka, P.V. Circ. Res. (1991) [Pubmed]
  10. Modulation of androgen receptor transactivation by gelsolin: a newly identified androgen receptor coregulator. Nishimura, K., Ting, H.J., Harada, Y., Tokizane, T., Nonomura, N., Kang, H.Y., Chang, H.C., Yeh, S., Miyamoto, H., Shin, M., Aozasa, K., Okuyama, A., Chang, C. Cancer Res. (2003) [Pubmed]
  11. Effect of the multidrug resistance protein on the transport of the antiandrogen flutamide. Grzywacz, M.J., Yang, J.M., Hait, W.N. Cancer Res. (2003) [Pubmed]
  12. The transcriptional co-activator cAMP response element-binding protein-binding protein is expressed in prostate cancer and enhances androgen- and anti-androgen-induced androgen receptor function. Comuzzi, B., Lambrinidis, L., Rogatsch, H., Godoy-Tundidor, S., Knezevic, N., Krhen, I., Marekovic, Z., Bartsch, G., Klocker, H., Hobisch, A., Culig, Z. Am. J. Pathol. (2003) [Pubmed]
  13. Comparison of the Pharmacological Effects of a Novel Selective Androgen Receptor Modulator (SARM), the 5alpha-Reductase Inhibitor Finasteride, and the Antiandrogen Hydroxyflutamide in Intact Rats: New Approach for Benign Prostate Hyperplasia (BPH). Seftel, A. J. Urol. (2005) [Pubmed]
  14. Effects of dihydrotestosterone and hydroxyflutamide on androgen receptors in cultured human breast cancer cells (EVSA-T). Marugo, M., Bernasconi, D., Miglietta, L., Fazzuoli, L., Ravera, F., Cassulo, S., Giordano, G. J. Steroid Biochem. Mol. Biol. (1992) [Pubmed]
  15. Suppression of Delta(5)-androstenediol-induced androgen receptor transactivation by selective steroids in human prostate cancer cells. Chang, H.C., Miyamoto, H., Marwah, P., Lardy, H., Yeh, S., Huang, K.E., Chang, C. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  16. Androgen sensitivity of the new human breast cancer cell line MFM-223. Hackenberg, R., Lüttchens, S., Hofmann, J., Kunzmann, R., Hölzel, F., Schulz, K.D. Cancer Res. (1991) [Pubmed]
  17. Androgen receptor antagonist versus agonist activities of the fungicide vinclozolin relative to hydroxyflutamide. Wong, C., Kelce, W.R., Sar, M., Wilson, E.M. J. Biol. Chem. (1995) [Pubmed]
  18. Androgen and epidermal growth factor down-regulate cyclin-dependent kinase inhibitor p27Kip1 and costimulate proliferation of MDA PCa 2a and MDA PCa 2b prostate cancer cells. Ye, D., Mendelsohn, J., Fan, Z. Clin. Cancer Res. (1999) [Pubmed]
  19. Transcriptional up-regulation of the human androgen receptor by androgen in bone cells. Wiren, K.M., Zhang, X., Chang, C., Keenan, E., Orwoll, E.S. Endocrinology (1997) [Pubmed]
  20. The anti-androgen hydroxyflutamide and androgens inhibit interleukin-6 production by an androgen-responsive human osteoblastic cell line. Hofbauer, L.C., Ten, R.M., Khosla, S. J. Bone Miner. Res. (1999) [Pubmed]
  21. Interference with the preovulatory luteinizing hormone surge and blockade of ovulation in immature pregnant mare's serum gonadotropin-primed rats with the anti-androgenic drug, hydroxyflutamide. Opavsky, M.A., Chandrasekhar, Y., Roe, M., Armstrong, D.T. Biol. Reprod. (1987) [Pubmed]
  22. Measurement of androgen sensitivity in the human prostate in in vitro three-dimensional histoculture. Geller, J., Sionit, L.R., Connors, K., Hoffman, R.M. Prostate (1992) [Pubmed]
  23. Androgen independence of primary epithelial cultures of the prostate is associated with a down-regulation of androgen receptor gene expression. Grant, E.S., Batchelor, K.W., Habib, F.K. Prostate (1996) [Pubmed]
  24. Promotion of agonist activity of antiandrogens by the androgen receptor coactivator, ARA70, in human prostate cancer DU145 cells. Miyamoto, H., Yeh, S., Wilding, G., Chang, C. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  25. The subnuclear three-dimensional image analysis of androgen receptor fused to green fluorescence protein. Tomura, A., Goto, K., Morinaga, H., Nomura, M., Okabe, T., Yanase, T., Takayanagi, R., Nawata, H. J. Biol. Chem. (2001) [Pubmed]
  26. Steroid requirement for androgen receptor dimerization and DNA binding. Modulation by intramolecular interactions between the NH2-terminal and steroid-binding domains. Wong, C.I., Zhou, Z.X., Sar, M., Wilson, E.M. J. Biol. Chem. (1993) [Pubmed]
  27. Activation of mitogen-activated protein kinase pathway by the antiandrogen hydroxyflutamide in androgen receptor-negative prostate cancer cells. Lee, Y.F., Lin, W.J., Huang, J., Messing, E.M., Chan, F.L., Wilding, G., Chang, C. Cancer Res. (2002) [Pubmed]
  28. Nongenomic androgen activation of phosphatidylinositol 3-kinase/Akt signaling pathway in MC3T3-E1 osteoblasts. Kang, H.Y., Cho, C.L., Huang, K.L., Wang, J.C., Hu, Y.C., Lin, H.K., Chang, C., Huang, K.E. J. Bone Miner. Res. (2004) [Pubmed]
  29. Acquisition of agonistic properties of nonsteroidal antiandrogens after treatment with oncostatin M in prostate cancer cells. Godoy-Tundidor, S., Hobisch, A., Pfeil, K., Bartsch, G., Culig, Z. Clin. Cancer Res. (2002) [Pubmed]
  30. Expression and function of androgen receptor coactivators in prostate cancer. Culig, Z., Comuzzi, B., Steiner, H., Bartsch, G., Hobisch, A. J. Steroid Biochem. Mol. Biol. (2004) [Pubmed]
  31. Differential modulation of androgen receptor transcriptional activity by the nuclear receptor co-repressor (N-CoR). Berrevoets, C.A., Umar, A., Trapman, J., Brinkmann, A.O. Biochem. J. (2004) [Pubmed]
  32. Regulation of A Disintegrin And Metalloproteinase with ThromboSpondin Repeats-1 Expression in Human Endometrial Stromal Cells by Gonadal Steroids Involves Progestins, Androgens, and Estrogens. Wen, J., Zhu, H., Murakami, S., Leung, P.C., Maccalman, C.D. J. Clin. Endocrinol. Metab. (2006) [Pubmed]
  33. Androgen locally regulates rat bulbocavernosus and levator ani size. Rand, M.N., Breedlove, S.M. J. Neurobiol. (1992) [Pubmed]
  34. Steady-state hydroxyflutamide plasma levels after the administration of two dosage forms of flutamide. Asade, R.H., Prizont, L., Muiño, J.P., Tessler, J. Cancer Chemother. Pharmacol. (1991) [Pubmed]
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