Prorenone

Prorenone

Systematic (IUPAC) name
(1aS,5aR,5bS,7aS,8R,10aS,10bR,10cS)-5a,7a-Dimethyl-1,1a,3',4,4',5,5a,5b,6,7,7a,9,10,10a,10b,10c-hexadecahydro-3H,5'H-spiro[cyclopenta[a]cyclopropa[l]phenanthrene-8,2'-furan]-3,5'-dione
Identifiers
CAS Number	49848-04-6
PubChem	CID 170819
IUPHAR/BPS	2876
DrugBank	DB00700
ChemSpider	149344
Synonyms	3-(17β-Hydroxy-6β,7β-methylene-3-oxo-4-androsten-17α-yl)propionic acid γ-lactone
Chemical data
Formula	C23H30O3
Molar mass	354.48 g/mol
SMILES O=C6O[C@@]5([C@@]3([C@H]([C@@H]2[C@H]4[C@@H](/C1=C/C(=O)CC[C@]1(C)[C@H]2CC3)C4)CC5)C)CC6
InChI InChI=1S/C23H30O3/c1-21-7-3-13(24)11-18(21)14-12-15(14)20-16(21)4-8-22(2)17(20)5-9-23(22)10-6-19(25)26-23/h11,14-17,20H,3-10,12H2,1-2H3/t14-,15+,16-,17-,20+,21+,22-,23+/m0/s1 Key:RRHHMFQGHCFGMH-LAPLKBAYSA-N

Prorenone (code names SC-23133, AC1L56BB) is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone that was never marketed.

Chemical synthesis

Prorenone can be synthesized via a Johnson–Corey–Chaykovsky reaction by reaction of canrenone with trimethylsulfonium iodide and sodium hydride.^[1]

See also

• Canrenone
• Mexrenone
• Potassium canrenoate

References

1. Chinn, L.; 1974, U.S. Patent 3,845,041