Spirolactone
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Spirolactones, also known as steroid-17α-spirolactones, 17α-spirolactosteroids, or simply as 17α-spirolactones, are a group of steroidal compounds which are both spiro compounds and lactones and which feature these two structural properties combined in the form of a spirolactone ring at the 17α position.[1][2][3] They are antimineralocorticoids, or antagonists of the mineralocorticoid receptor (which is activated predominantly by the mineralocorticoid steroid hormone aldosterone), and have been employed clinically as potassium-sparing diuretics.[1][3][4][5] Some also possess progestogenic, antigonadotropic, and/or antiandrogen properties, which have both contributed to side effects and been utilized for medical indications (e.g., spironolactone as an antiandrogen, and drospirenone as a progestin).[1][3][6] The spirolactones were developed by G. D. Searle & Company in the 1950s and thereafter and were denoted as "SC" compounds (e.g., SC-9420 for spironolactone).[1][5]
The spirolactones include the marketed drugs spironolactone (SC-9420; Aldactone), canrenone (SC-9376; Cantaren, Luvion), potassium canrenoate (SC-14266; Venactone, Soldactone), eplerenone (SC-66110; Inspra), and drospirenone (ZK-30595; Yasmin). Spirolactones that were not ever marketed include SC-5233,[4] SC-8109,[4] dicirenone (SC-26304), mespirenone (ZK-94679), mexrenone (SC-25152, ZK-32055), prorenone (SC-23133), spirorenone (ZK-35973), and spiroxasone. Oxprenoate potassium (RU-28318) is not a spirolactone by definition but is a closely related antimineralocorticoid that was never marketed.
SC-5233, the propanoic acid lactone of 17β-hydroxyandrosterone, is the unsubstituted parent or prototype compound of the spirolactones, and is one of a few of the simplest members of the series along with SC-8109 (the 19-nor (19-demethyl) analogue of SC-5233) and canrenone (the 1,2-didehydro analogue of SC-5233).[1][2][7] Spironolactone is a derivative of SC-5233 with a 7α-acetylthio group (that is, SC-5233 is 7-desthioacetylspironolactone).[1]
See also
References
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