ATC code None PubChem CID 170819 DrugBank DB00700 Pubchem 170819 IUPHAR/BP 2876 | CAS Number 49848-04-6 IUPHAR/BPS 2876 Molar mass 354.48 g/mol ChemSpider ID 149344 | |
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Synonyms SC-23133; 3-(17β-Hydroxy-6β,7β-methylene-3-oxo-4-androsten-17α-yl)propionic acid γ-lactone | ||
Prorenone (developmental code name SC-23133) is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone that was never marketed. It is the lactonic form of prorenoic acid (prorenoate), and prorenoate potassium (SC-23992), the potassium salt of prorenoic acid, also exists. Prorenoate potassium is about 8 times more potent than spironolactone as an antimineralocorticoid in animals, and it may act as a prodrug to prorenone. In addition to the mineralocorticoid receptor, prorenone also binds to the glucocorticoid, androgen, and progesterone receptors. Similarly to spironolactone, prorenone is also a potent inhibitor of aldosterone biosynthesis.
Chemical synthesis
Prorenone can be synthesized via a Johnson–Corey–Chaykovsky reaction by reaction of canrenone with trimethylsulfonium iodide and sodium hydride.