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Other names | SC-23133; 3-(17β-Hydroxy-6β,7β-methylene-3-oxo-4-androsten-17α-yl)propionic acid γ-lactone |
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Formula | C23H30O3 |
Molar mass | 354.490 g·mol−1 |
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Prorenone (developmental code name SC-23133) is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone that was never marketed. [1] It is the lactonic form of prorenoic acid (prorenoate), and prorenoate potassium (SC-23992), the potassium salt of prorenoic acid, also exists. [1] Prorenoate potassium is about 8 times more potent than spironolactone as an antimineralocorticoid in animals, and it may act as a prodrug to prorenone. [1] In addition to the mineralocorticoid receptor, prorenone also binds to the glucocorticoid, androgen, and progesterone receptors. [2] [3] The antiandrogenic potency of prorenone in vivo in animals is close to that of spironolactone. [3] Similarly to spironolactone, prorenone is also a potent inhibitor of aldosterone biosynthesis. [4]
Prorenone can be synthesized via a Johnson–Corey–Chaykovsky reaction by reaction of canrenone with trimethylsulfoxonium iodide and sodium hydride. [5]