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 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.
D000818:Animals; D002369:Castration; D055598:Chemical Phenomena; D002621:Chemistry; D005260:Female; D008297:Male; D000451:Mineralocorticoid Receptor Antagonists / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology*; D010060:Ovulation / Q000187:drug effects; D011817:Rabbits; D051381:Rats; D011919:Rats, Inbred Strains; D011944:Receptors, Androgen; D011980:Receptors, Progesterone / Q000378:metabolism; D013148:Spironolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014599:Uterus / Q000187:drug effects
D000451:Mineralocorticoid Receptor Antagonists; D011944:Receptors, Androgen; D011980:Receptors, Progesterone; D013148:Spironolactone