Spirolactone

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The first three skeletal formulae belong to spirolactone antimineralocorticoids.

Spirolactones are a class of functional group in

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

7α-thiomethylspironolactone (SC-26519), mexrenoate potassium (SC-26714), spirorenone (ZK-35973), ZK-91587 (15β,16β-methylenemexrenone), mespirenone (ZK-94679), and ZK-97894 (7α-thiomethylmespirenone). Oxprenoate potassium
(RU-28318) is not a spirolactone by definition but is a closely related antimineralocorticoid that was never marketed.

SC-5233 (6,7-dihydrocanrenone), the C17α

prototype compound of the spirolactones, and is one of a few of the simplest members of the series along with SC-8109 (the 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 7α-desthioacetylspironolactone).[1]

Chemical structures of spirolactones
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Chemical structures of progesterone and spirolactones (steroid-17α-spirolactones).

See also

References