Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones

Some 15,16-methylene derivatives of the aldosterone antagonist spironolactone were synthesized with the purpose of increasing the antialdosterone potency and reducing the endocrinological effects of this standard compound. By introduction of a 1,2-double bond and a 15 beta,16 beta-methylene ring in...

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Veröffentlicht in:	Journal of medicinal chemistry 1987-08, Vol.30 (8), p.1403-1409
Hauptverfasser:	Nickisch, K, Bittler, D, Laurent, H, Losert, W, Casals-Stenzel, J, Nishino, Y, Schillinger, E, Wiechert, R
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Castration Chemical Phenomena Chemistry Female Male Mineralocorticoid Receptor Antagonists - chemical synthesis Mineralocorticoid Receptor Antagonists - metabolism Mineralocorticoid Receptor Antagonists - pharmacology Ovulation - drug effects Rabbits Rats Rats, Inbred Strains Receptors, Androgen Receptors, Progesterone - metabolism Spironolactone - analogs & derivatives Spironolactone - chemical synthesis Spironolactone - metabolism Spironolactone - pharmacology Structure-Activity Relationship Uterus - drug effects
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Zusammenfassung:	Some 15,16-methylene derivatives of the aldosterone antagonist spironolactone were synthesized with the purpose of increasing the antialdosterone potency and reducing the endocrinological effects of this standard compound. By introduction of a 1,2-double bond and a 15 beta,16 beta-methylene ring in the spironolactone molecule both goals were achieved. In animal studies mespirenone exhibited a threefold-greater antialdosterone potency and less than 10% of the antiandrogenic activity of spironolactone.
ISSN:	0022-2623
DOI:	10.1021/jm00391a023