SC-5233

SC-5233

Systematic (IUPAC) name
(8R,9S,10R,13S,14S,17R)-10,13-Dimethylspiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione
Clinical data
Routes of administration	Oral
Identifiers
CAS Number	976-70-5
ATC code	None
PubChem	CID: 101931
ChemSpider	92091
Synonyms	20-Spirox-4-ene-3,20-dione, 6,7-dihydrocanrenone, 7-desthioacetylspironolactone, 17β-Hydroxyandrost-4-en-3-one-17α-propionic acid lactone
Chemical data
Formula	C22H30O3
Molecular mass	342.4718 g/mol
SMILES CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC45CCC(=O)O5)C
InChI InChI=1S/C22H30O3/c1-20-9-5-15(23)13-14(20)3-4-16-17(20)6-10-21(2)18(16)7-11-22(21)12-8-19(24)25-22/h13,16-18H,3-12H2,1-2H3/t16-,17+,18+,20+,21+,22-/m1/s1 Key:UWBICEKKOYXZRG-WNHSNXHDSA-N

SC-5233 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 propanoic acid lactone of 17β-hydroxyandrosterone. It is the unsubstituted parent or prototype compound of the spirolactone family of steroidal antimineralocorticoids.

See also

• Canrenone