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Chemical Compound Review

Cyanoketone     (2R,8R,9S,10R,13S,14S,17S)- 17-hydroxy-4,4...

Synonyms: SureCN18925, AC1L2FUP, LS-19421, BRN 5763422, 4248-66-2, ...
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Disease relevance of Cyanoketone

  • Cyanoketone blocked the stress-induced rise in IL-6 mRNA and protein expression in the trigeminal ganglion latently infected with HSV-1 [1].
  • These studies were performed to determine how bilateral adrenal hypertrophy persists despite normal resting ACTH levels in male rats for weeks after a 3-day course of treatment with cyanoketone (CK) [2].

High impact information on Cyanoketone

  • Cyanoketone completely blocked FSH- or 8-Br-cAMP-induced fibronectin production by F3 cells, but caused only a modest inhibition (nonsignificant) of agonist-induced fibronectin production by SYF cells [3].
  • In Exp II, granulosa cells (3 x 10(5)/3 were incubated for 0-12 h in triplicate for each combined treatments of 25-OH-cholesterol (8 microM) and cyanoketone (10 microM), T, or E2 (0-10 microM) in the presence or absence of LH (25 ng) [4].
  • The stimulation by 5-androstene-3 beta,17 beta-diol is inhibited by antiestrogens, but it is not blocked by the delta 5-3 beta-hydroxysteroid isomerase/dehydrogenase inhibitor, cyanoketone, or by the aromatase inhibitor, 4-hydroxy-androstenedione [5].
  • An isolated perfused rabbit ovary preparation was used to determine the effects of cyanoketone, a potent inhibitor of 3 beta-hydroxysteroid dehydrogenase, on ovulation, ovum maturation and fertilizability, and steroid production [6].
  • Interaction of cyanoketone and other steroid nitriles with cytochrome oxidase, hemoglobin, and cytochrome P-450 [7].

Biological context of Cyanoketone

  • The inhibitory activity of cyanoketone (CNK; 2alpha-cyano-4,4,17alpha-trimethyl-17beta-hydroxy-5-androsten-3-one), was investigated for enzymes of the respiratory chain and cholesterol side chain cleavage (CSCC) [7].
  • Both upregulation of the MIS receptor and development of OMC in response to gonadotropin were blocked by coincubation with actinomycin D or cycloheximide, which are inhibitors of mRNA and protein synthesis, respectively, but not by cyanoketone, which is an inhibitor of 3 beta-hydroxysteroid dehydrogenase-dependent steroid synthesis [8].
  • The results indicate that ACTH causes a significant dose-response stimulation of delta 5-3 beta-HSD activity in tadpole interrenals; cyanoketone, on the other hand, causes significant dose-dependent inhibition [9].
  • The selective effects of trilostane and cyanoketone on the 3 beta-HSD-Is involved in the androgen and 16-androstene biosynthetic pathways strongly suggest that the reactions are catalysed by separate enzymes, or at least separate, non-interacting active sites on a single enzyme [10].
  • It is concluded that the previously observed sex differences in response to cyanoketone in vivo are not due to a lower affinity of male adrenal 3beta-hydroxy-delta5-steroid oxidoreductase to cyanoketone [11].

Anatomical context of Cyanoketone

  • The aim of the present studies was to investigate the reactions further by examining the effects of two classical steroidal inhibitors of 3 beta-HSD-I, trilostane (WIN 24540) and cyanoketone (WIN 19578), on the kinetic parameters of the 3 beta-HSD-I reactions in immature (< 3 weeks) pig testis microsomes [10].
  • Effects of prolonged treatment with cyanoketone on the zona fasciculata of rat adrenal cortex. A combined morphometric and biochemical study [12].
  • Inhibitors of the 3 beta-hydroxysteroid dehydrogenase/isomerase (trilostane and cyanoketone) significantly reduced formation of 19-norT in small porcine luteal cells and 19-norA in large porcine luteal cells, although they were effective at different concentrations in each cell type [13].
  • Contrasting effects of ACTH and cyanoketone on delta 5-3 beta-hydroxysteroid dehydrogenase activity in interrenal glands of tadpoles of Rana catesbeiana in vitro [9].
  • However, in C. mrigala, when the oocytes were incubated with cyanoketone or epostane along with LH, the rate of GVBD was not induced significantly at their lowest concentration but four other higher concentrations could inhibit the LH-induced GVBD [14].

Associations of Cyanoketone with other chemical compounds


Gene context of Cyanoketone

  • A competitive inhibition of the 20 alpha-hydroxysteroid dehydrogenase (20 alpha-HSDH) by azastene (I50 = 0.6 microM), trilostane (I50 = 4.1 microM), cyanoketone (I50 = 0.6 microM), and WIN 32,729 (I50 = 1.5 microM) was observed [18].
  • However, the in vivo inhibition of LPS-induced IL-1beta by UCN was reversed by cyanoketone, indicating that the increase of endogenous glucocorticoids might be more important in IL-1beta inhibition than in TNF inhibition by UCN [19].
  • Concentrations of 0.01, 0.1, 1, and 10 IU/ml of ACTH or of 0.01, 0.1, 1, and 10 micrograms/ml of cyanoketone were added to the incubation media [9].
  • Blockade of steroidogenesis with cyanoketone also had no effect on the cathepsin-D activity of isolated granulosa cells [20].
  • Treatment of croaker testicular tissue in vitro with gonadotropin caused a several-fold increase in sperm mPR receptor concentrations that was partially blocked in the presence of cyanoketone, which suggests this action of gonadotropin is partially mediated by stimulation of steroidogenesis [21].

Analytical, diagnostic and therapeutic context of Cyanoketone


  1. Role of the hypothalamic pituitary adrenal axis and IL-6 in stress-induced reactivation of latent herpes simplex virus type 1. Noisakran, S., Halford, W.P., Veress, L., Carr, D.J. J. Immunol. (1998) [Pubmed]
  2. Drug-induced adrenal hypertrophy provides evidence for reset in the adrenocortical system. Akana, S.F., Shinsako, J., Dallman, M.F. Endocrinology (1983) [Pubmed]
  3. Intracrine role of progesterone in follicle-stimulating hormone- and cyclic adenosine 3',5'-monophosphate-induced fibronectin production and deposition by chicken granulosa cells: influence of follicular development. Conkright, M.D., Asem, E.K. Endocrinology (1995) [Pubmed]
  4. Inhibition of the activities of P450 cholesterol side-chain cleavage and 3 beta-hydroxysteroid dehydrogenase and the amount of P450 cholesterol side-chain cleavage by testosterone and estradiol-17 beta in hen granulosa cells. Lee, H.T., Bahr, J.M. Endocrinology (1990) [Pubmed]
  5. A simple and sensitive microtiter plate estrogen bioassay based on stimulation of alkaline phosphatase in Ishikawa cells: estrogenic action of delta 5 adrenal steroids. Littlefield, B.A., Gurpide, E., Markiewicz, L., McKinley, B., Hochberg, R.B. Endocrinology (1990) [Pubmed]
  6. Are ovarian steroids required for ovum maturation and fertilization? Effects of cyanoketone on the in vitro perfused rabbit ovary. Yoshimura, Y., Hosoi, Y., Bongiovanni, A.M., Santulli, R., Atlas, S.J., Wallach, E.E. Endocrinology (1987) [Pubmed]
  7. Interaction of cyanoketone and other steroid nitriles with cytochrome oxidase, hemoglobin, and cytochrome P-450. Graves, P.E., Uzgiris, V.I., Querner, M., Kashiwagi, K., McIntosh, E.N., Salhanick, H.A. Endocrinology (1978) [Pubmed]
  8. Upregulation of the maturation-inducing steroid membrane receptor in spotted seatrout ovaries by gonadotropin during oocyte maturation and its physiological significance. Thomas, P., Pinter, J., Das, S. Biol. Reprod. (2001) [Pubmed]
  9. Contrasting effects of ACTH and cyanoketone on delta 5-3 beta-hydroxysteroid dehydrogenase activity in interrenal glands of tadpoles of Rana catesbeiana in vitro. Yu, N.W., Ku, H.H., Chang, L.T., Hsu, C.Y. Cell Tissue Res. (1987) [Pubmed]
  10. Differential effects of trilostane and cyanoketone on the 3 beta-hydroxysteroid dehydrogenase-isomerase reactions in androgen and 16-androstene biosynthetic pathways in the pig testis. Cooke, G.M. J. Steroid Biochem. Mol. Biol. (1996) [Pubmed]
  11. Cyanoketone-induced inhibition of adrenal 3beta-hydroxy-delta5-steroid oxidoreductase activity in female and male rats in vitro. Gustafsson, S.A. Acta Endocrinol. (1976) [Pubmed]
  12. Effects of prolonged treatment with cyanoketone on the zona fasciculata of rat adrenal cortex. A combined morphometric and biochemical study. Robba, C., Mazzocchi, G., Gottardo, G., Meneghelli, V., Nussdorfer, G.G. Cell Tissue Res. (1987) [Pubmed]
  13. Conversion of 5(10)-oestrene-3 beta,17 beta-diol to 19-nor-4-ene-3-ketosteroids by luteal cells in vitro: possible involvement of the 3 beta-hydroxysteroid dehydrogenase/isomerase. Lee, C.M., Tekpetey, F.R., Armstrong, D.T., Khalil, M.W. J. Endocrinol. (1991) [Pubmed]
  14. In vitro effects of cyanoketone and epostane on LH-induced germinal vesicle breakdown in oocytes of Indian major carps. Haider, S., Inbaraj, R.M. Gen. Comp. Endocrinol. (1989) [Pubmed]
  15. Intracrine role of progesterone in fibronectin production and deposition by chicken ovarian granulosa cells in vitro: effect of extracellular calcium. Conkright, M.D., Asem, E.K. Biol. Reprod. (1995) [Pubmed]
  16. Effect of pregnant mare serum gonadotropin on the induction and degradation of FSH and LH receptors in the granulosa cell of the immature rat. Vidyashankar, N., Moudgal, N.R. Mol. Cell. Endocrinol. (1984) [Pubmed]
  17. The effect of azastene, cyanoketone and trilostane upon respiration and cleavage of the cholesterol side chain in mitochondria from bovine adrenal cortex. Shears, S.B., Boyd, G.S. Eur. J. Biochem. (1981) [Pubmed]
  18. Inhibition of human placental progesterone synthesis and aromatase activity by synthetic steroidogenic inhibitors in vitro. Rabe, T., Kiesel, L., Kellermann, J., Weidenhammer, K., Runnebaum, B., Potts, G.O. Fertil. Steril. (1983) [Pubmed]
  19. Corticosteroid-independent inhibition of tumor necrosis factor production by the neuropeptide urocortin. Agnello, D., Bertini, R., Sacco, S., Meazza, C., Villa, P., Ghezzi, P. Am. J. Physiol. (1998) [Pubmed]
  20. Studies on follicular atresia: role of tropic hormone and steroids in regulating cathepsin-D activity of preantral follicles of the immature rat. Dhanasekaran, N., Moudgal, N.R. Mol. Cell. Endocrinol. (1986) [Pubmed]
  21. Binding characteristics, hormonal regulation and identity of the sperm membrane progestin receptor in Atlantic croaker. Thomas, P., Tubbs, C., Detweiler, C., Das, S., Ford, L., Breckenridge-Miller, D. Steroids (2005) [Pubmed]
  22. Relationships among adrenal weight, corticosterone, and stimulated adrenocorticotropin levels in rats. Akana, S.F., Shinsako, J., Dallman, M.F. Endocrinology (1983) [Pubmed]
  23. Therapy of dimethylbenzanthracene-induced mammary carcinomas in the rat by selective inhibition of steroidogenesis. Levin, J.M., Goldman, A.S., Rosato, F.E., Rosato, E.E. Cancer (1976) [Pubmed]
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