Summary: 2 alpha-Cyano-17 beta-hydroxy-4,4',17 alpha-trimethylandrost-5-ene-3-one. An androstenolone-nitrile compound with steroidogenesis-blocking activity.

Top Publications

  1. Cooke G. 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. J Steroid Biochem Mol Biol. 1996;58:95-101 pubmed 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 ..
  2. Kobayashi T, Sakai N, Adachi S, Asahina K, Iwasawa H, Nagahama Y. 17 alpha,20 alpha-Dihydroxy-4-pregnen-3-one is the naturally occurring spermiation-inducing hormone in the testis of a frog, Rana nigromaculata. Endocrinology. 1993;133:321-7 pubmed
    ..These findings provide evidence that 17 alpha,20 alpha-DP is the nautrally occurring spermiation-inducing hormone in R. nigromaculata. ..
  3. Regueira E, Sassone A, Scaia M, Volonteri M, Ceballos N. Seasonal changes and regulation of the glucocorticoid receptor in the testis of the toad Rhinella arenarum. J Exp Zool A Ecol Genet Physiol. 2013;319:39-52 pubmed publisher
    ..of melatonin (40 and 200 pg/ml), with or without luzindole (melatonin-receptor antagonist); with testosterone, cyanoketone (inhibitor of steroidogenesis) or casodex (androgen-receptor antagonist); or with dexamethasone or RU486 (GR ..
  4. Pozzi A, Ceballos N. Human chorionic gonadotropin-induced spermiation in Bufo arenarum is not mediated by steroid biosynthesis. Gen Comp Endocrinol. 2000;119:164-71 pubmed
    ..b>Cyanoketone (10(-5)-10(-6) M), an inhibitor of 3-oxo-4-ene steroid biosynthesis, did not block hCG-inducing activity even ..
  5. Proctor G, Harvey A. Synthesis of tacrine analogues and their structure-activity relationships. Curr Med Chem. 2000;7:295-302 pubmed
    ..However, some halogenated derivatives are not only more potent acetylcholinesterase inhibitors than tacrine, they are also more selective for acetylcholinesterase than for butyrylcholinesterase. ..
  6. Fantuzzi G, Demitri M, Ghezzi P. Differential effect of glucocorticoids on tumour necrosis factor production in mice: up-regulation by early pretreatment with dexamethasone. Clin Exp Immunol. 1994;96:166-9 pubmed
    ..This up-regulating effect was not observed in adrenalectomized mice or when GC synthesis was inhibited with cyanoketone (CK)...
  7. Contreras H, Ronco A. Leydig cell heterogeneity as judged by quantitative cytochemistry of 3 beta-hydroxysteroid dehydrogenase activity in individual rat Leydig cells. J Steroid Biochem Mol Biol. 1994;51:73-9 pubmed
    ..The results describe for the first time that the 3 beta-HSD activity may be differentially regulated by LH/hCG in Leydig cells. ..
  8. Robba C, Mazzocchi G, Gottardo G, Meneghelli V, Nussdorfer G. Effects of prolonged treatment with cyanoketone on the zona fasciculata of rat adrenal cortex. A combined morphometric and biochemical study. Cell Tissue Res. 1987;250:599-605 pubmed
    The effects of a 7-day administration of cyanoketone (CKT) on the adrenal zona fasciculata were examined in "normal" and dexamethasone/ACTH-infused rats...
  9. Patino R, Thomas P. Effects of gonadotropin on ovarian intrafollicular processes during the development of oocyte maturational competence in a teleost, the Atlantic croaker: evidence for two distinct stages of gonadotropin control of final oocyte maturation. Biol Reprod. 1990;43:818-27 pubmed
    ..or hCG-primed fish, the direct effects of steroids on maturational competence, and the effects of steroid (cyanoketone), protein (cycloheximide), and RNA (actinomycin D) synthesis inhibitors on hCG-induced maturational competence ..

More Information


  1. Haider S, Inbaraj R. In vitro effects of cyanoketone and epostane on LH-induced germinal vesicle breakdown in oocytes of Indian major carps. Gen Comp Endocrinol. 1989;73:92-5 pubmed
    The effect of cyanoketone (inhibitor of delta 5-3 beta-hydroxysteroid dehydrogenase) and epostane (inhibitor of 3 beta-hydroxysteroid dehydrogenase) on LH-induced in vitro germinal vesicle breakdown (GVBD) in the oocytes of Indian major ..
  2. Yu N, Ku H, Chang L, Hsu C. Contrasting effects of ACTH and cyanoketone on delta 5-3 beta-hydroxysteroid dehydrogenase activity in interrenal glands of tadpoles of Rana catesbeiana in vitro. Cell Tissue Res. 1987;250:585-8 pubmed
    ..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...
  3. Hsu C, Chang L, Yu N, Ku H, Lu M. In vitro inhibition of estradiol secretion of tadpole ovaries by cyanoketone. Gen Comp Endocrinol. 1988;69:41-5 pubmed
    ..present study, we wish to determine whether estradiol (E2) secretion of tadpole ovaries could be influenced by cyanoketone (CK), a specific inhibitor of delta 5-3 beta-HSD...
  4. Conkright M, Asem E. 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. Endocrinology. 1995;136:2641-51 pubmed
    ..b>Cyanoketone (an inhibitor of progesterone synthesis) significantly suppressed basal fibronectin production by F3 cells, but ..
  5. Friberg P, Larsson D, Billig H. Dominant role of nuclear progesterone receptor in the control of rat periovulatory granulosa cell apoptosis. Biol Reprod. 2009;80:1160-7 pubmed publisher
    ..Concurrently, P4 synthesis was decreased. Inhibition of P4 synthesis by cyanoketone similarly induced apoptosis but required greater inhibition of P4 synthesis than that seen after treatment with ..
  6. Canosa L, Ceballos N. Effects of different steroid-biosynthesis inhibitors on the testicular steroidogenesis of the toad Bufo arenarum. J Comp Physiol B. 2001;171:519-26 pubmed
    ..7-(3)H]testosterone (T), and different steroid-biosynthesis inhibitors. The inhibitors used were: cyanoketone (CNK), spironolactone (SPNL) and finasteride (FIN)...
  7. Magarinos A, McEwen B. Stress-induced atrophy of apical dendrites of hippocampal CA3c neurons: involvement of glucocorticoid secretion and excitatory amino acid receptors. Neuroscience. 1995;69:89-98 pubmed
    ..Treatment of chronically stressed rats with the steroid synthesis blocker cyanoketone prevented stress-induced dendritic atrophy...
  8. Chesnel F, Bourry A, Boujard D, Joly J. A nonsteroidal follicular factor is involved in maturation process of Xenopus laevis oocytes. Gen Comp Endocrinol. 1992;86:304-12 pubmed
    ..The potentiating activity is suppressed when follicles are incubated with cyanoketone to inhibit steroidogenesis, suggesting that the secretion of the potentiating factor can be modulated in vitro...
  9. Hsieh M, Shia K, Liu H, Kuo S. Palladium(II) acetate mediated oxidative cyclization of ?-unsaturated ?-cyano ketones for facile construction of methylenecyclohexane ring system. Org Biomol Chem. 2012;10:4609-17 pubmed publisher
    ..Based on this newly developed protocol, polycyclic adducts bearing various ring sizes and substitutions can be prepared in moderate to high yields. ..
  10. Espallergues J, Temsamani J, Laruelle C, Urani A, Maurice T. The antidepressant-like effect of the 3?-hydroxysteroid dehydrogenase inhibitor trilostane involves a regulation of ?-type estrogen receptors. Psychopharmacology (Berl). 2011;214:455-63 pubmed publisher
    ..We compared the behavioral effect of trilostane with the other 3?-HSD inhibitor, cyanoketone, and analyzed the putative involvement of the ?-type estrogen receptor (ER?) in its antidepressant effect...
  11. Weber G, Sullivan C. Effects of insulin-like growth factor-I on in vitro final oocyte maturation and ovarian steroidogenesis in striped bass, Morone saxatilis. Biol Reprod. 2000;63:1049-57 pubmed
    ..Incubation of MIS-competent follicles with actinomycin D, cyanoketone, trilostane, 1-heptanol, or 1-octanol had no effect on rhIGF-I-induced GVBD, but attenuated hCG-induced GVBD ..
  12. Aragones A, Gonzalez C, Spinedi N, Lantos C. Regulatory effects of 5 beta-reduced steroids. J Steroid Biochem Mol Biol. 1991;39:253-63 pubmed
    ..e. the synthesis of progesterone and higher hydroxylated steroids, by steroidogenic glands in the event of an excessive precursor reduction. ..
  13. Haider S, Chaube S. The in vitro effects of forskolin, IBMX and cyanoketone on meiotic maturation in follicle-enclosed catfish (Clarias batrachus) oocytes. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1996;115:117-23 pubmed
    ..FK), phosphodiesterase inhibitor (3-isobutyl-l-methyl-xanthine, IBMX) and an inhibitor of steroidogenesis (cyanoketone, CK) on germinal vesicle breakdown (GVBD) in the catfish (Clarias batrachus) were investigated in vitro...
  14. Haider S. Further experimental evidence in support of the involvement of ovarian follicles in oocyte maturation of the Indian catfish, Mystus vittatus. Gen Comp Endocrinol. 1990;80:80-4 pubmed
    ..layer in the oocyte maturation of the Indian catfish, Mystus vittatus, was investigated in vitro using cyanoketone and epostane (specific inhibitors of the 3 beta-hydroxysteroid dehydrogenase enzyme system)...
  15. Shalem Z, Izhar M, Shore L, Shemesh M, Hansel W, Strauss J. Control of bovine placental progestin synthesis: calcium dependent steroidogenesis is modulated at the site of the cholesterol side chain cleavage enzyme. J Steroid Biochem. 1988;31:835-8 pubmed
    ..In experiments in which cyanoketone, an agent that inhibits the conversion of pregnenolone to progesterone, was added, TPA addition resulted in ..
  16. Asem E, Conkright M. Role of progesterone in luteinizing hormone-induced fibronectin production and deposition by chicken granulosa cells in vitro. Comp Biochem Physiol C Pharmacol Toxicol Endocrinol. 1995;112:247-55 pubmed
    ..Similarly, it increased the quantity of fibronectin secreted into the medium or associated with cells. Cyanoketone (an inhibitor of progesterone synthesis) suppressed dose dependently basal and LH-induced fibronectin ..
  17. Noisakran S, Halford W, Veress L, Carr D. Role of the hypothalamic pituitary adrenal axis and IL-6 in stress-induced reactivation of latent herpes simplex virus type 1. J Immunol. 1998;160:5441-7 pubmed
    ..of the putative role of IL-6 in facilitating HSV-1 reactivation in mice, the effect of hyperthermic stress and cyanoketone treatment on IL-6 expression in the trigeminal ganglion was also measured...
  18. Agnello D, Bertini R, Sacco S, Meazza C, Villa P, Ghezzi P. Corticosteroid-independent inhibition of tumor necrosis factor production by the neuropeptide urocortin. Am J Physiol. 1998;275:E757-62 pubmed
    ..These effects were paralleled by a rise in corticosterone (CS) levels. Blockade of the CS increase by cyanoketone did not prevent TNF inhibition by UCN, suggesting the neuropeptide has anti-inflammatory mechanisms independent ..
  19. Takahashi M, Luu The V, Labrie F. Inhibitory effect of synthetic progestins, 4-MA and cyanoketone on human placental 3 beta-hydroxysteroid dehydrogenase/5----4-ene-isomerase activity. J Steroid Biochem Mol Biol. 1990;37:231-6 pubmed
    ..Trilostane, epostane and cyanoketone are potent inhibitors of 3 beta-HSD with Ki values of approximately 50 nM...
  20. Akana S, Dallman M, Bradbury M, Scribner K, Strack A, Walker C. Feedback and facilitation in the adrenocortical system: unmasking facilitation by partial inhibition of the glucocorticoid response to prior stress. Endocrinology. 1992;131:57-68 pubmed
    ..To test this hypothesis directly, we treated young male rats with cyanoketone (CK) to partially block the adrenal capacity to synthesize corticosterone (B)...
  21. Asem E, Conkright M, Novero R. Progesterone stimulates fibronectin production by chicken granulosa cells in vitro. Eur J Endocrinol. 1994;130:159-65 pubmed
    ..b>Cyanoketone (an inhibitor of progesterone synthesis) suppressed basal fibronectin production by F1 and F3 granulosa cells ..
  22. Akana S, Strack A, Hanson E, Dallman M. Regulation of activity in the hypothalamo-pituitary-adrenal axis is integral to a larger hypothalamic system that determines caloric flow. Endocrinology. 1994;135:1125-34 pubmed
  23. Anderson L, Zhou M, Sharma V, McLaughlin J, Santiago D, Fronczek F, et al. Facile iterative synthesis of 2,5-terpyrimidinylenes as nonpeptidic alpha-helical mimics. J Org Chem. 2010;75:4288-91 pubmed publisher
    ..These compounds are designed to mimic the i, i + 4, and i + 7 sites of an alpha-helix. ..
  24. Hsu C, Chang L, Yu N. Estrogen suppression of preincubated tadpole ovaries in vitro by cyanoketone. Proc Natl Sci Counc Repub China B. 1988;12:84-7 pubmed
    In a previous RIA study we found that cyanoketone (CK) inhibited ovarian E2 secretion of tadpoles in vitro and that this inhibition effect was through inactivation of delta 5-3 beta-HSD activity...
  25. Tsafriri A, Abisogun A, Reich R. Steroids and follicular rupture at ovulation. J Steroid Biochem. 1987;27:359-63 pubmed
    ..It seems, therefore, that follicular steroids, most probably estrogen, are involved in the preovulatory rise in follicular t-PA activity. ..
  26. Dhabhar F, Miller A, McEwen B, Spencer R. Stress-induced changes in blood leukocyte distribution. Role of adrenal steroid hormones. J Immunol. 1996;157:1638-44 pubmed
    ..b>Cyanoketone, a corticosterone (CORT) synthesis inhibitor, significantly reduced the decrease in lymphocyte numbers observed ..
  27. Neri G, Tortorella C, Andreis P, Bova S, Malendowicz L, Ziolkowska A, et al. Norbormide enhances late steps of steroid-hormone synthesis in rat and mouse adrenal cortex. J Steroid Biochem Mol Biol. 2003;84:479-83 pubmed
    ..aldosterone (ALDO), as well as large amounts of pregnenolone (PREG) when its metabolism was blocked by 10(-5)M cyanoketone. Norbormide concentration-dependently raised the secretion of all post-DOC steroids assayed, decreased ..