|Chemical and physical data|
|Molar mass||342.4718 g/mol|
|3D model (Jmol)||Interactive image|
SC-5233, also known as 6,7-dihydrocanrenone or 20-spirox-4-ene-3,20-dione, is a steroidal antimineralocorticoid of the spirolactone group that was developed by G. D. Searle & Company in the 1950s but was never marketed. It was the first antagonist of the mineralocorticoid receptor to have been identified and tested in humans. The drug was found to have poor oral bioavailability and potency, but it nonetheless produced a mild diuretic effect in patients with congestive heart failure. SC-8109, the 19-nor (19-demethyl) analogue, was developed and found to have improved oral bioavailability and potency, but still had relatively low potency. Spironolactone (SC-9420; Aldactone) followed and had both good oral bioavailability and potency, and was the first antimineralocorticoid to be marketed.
SC-5233 is the propionic acid lactone of 17β-hydroxyandrost-4-en-3-one or testosterone and is also known 3-(3-oxo-17β-hydroxyandrost-4-en-17α-yl)propionic acid γ-lactone or as 17α-(2-carboxyethyl)testosterone γ-lactone. It is the unsubstituted parent or prototype compound of the spirolactone family of steroidal antimineralocorticoids.
Similarly to other spirolactones like canrenone and spironolactone, SC-5233 has antiandrogen activity and antagonizes the effects of testosterone in animals. In addition, along with SC-8109, it has been found to possess potent progestogenic activity.
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