SC-5233

SC-5233

Clinical data
Other names	6,7-Dihydrocanrenone; 7-Desthioacetylspironolactone; 20-Spirox-4-ene-3,20-dione
Routes of administration	By mouth
Drug class	Antimineralocorticoid; Progestogen; Steroidal antiandrogen
ATC code	None
Identifiers
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
CAS Number	976-70-5
PubChem CID	101931
ChemSpider	92091
UNII	3N8TCN29OP
ChEMBL	ChEMBL400534
CompTox Dashboard (EPA)	DTXSID10875403
ECHA InfoCard	100.012.321
Chemical and physical data
Formula	C22H30O3
Molar mass	342.479 g·mol−1
3D model (JSmol)	Interactive image
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, also known as 6,7-dihydrocanrenone or 20-spirox-4-ene-3,20-dione, is a synthetic, steroidal antimineralocorticoid of the spirolactone group which was developed by G. D. Searle & Company in the 1950s but was never marketed. It was the first synthetic antagonist of the mineralocorticoid receptor to have been identified and tested in humans. The drug was found to lack appreciable oral bioavailability and to be of low potency when administered parenterally, 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 low potency.Spironolactone (SC-9420; Aldactone) followed and had both good oral bioavailability and potency, and was the first synthetic antimineralocorticoid to be marketed. It has about 46-fold higher oral potency than SC-5233.

SC-5233 is the propionic acid lactone of testosterone (androst-4-en-17β-ol-3-one) 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 some antiandrogenic activity and antagonizes the effects of testosterone in animals. In addition, along with SC-8109, it has been found to possess potent progestogenic activity.

v t e Chemical structures of spirolactones Progesterone Spirolactone Canrenone Spironolactone Drospirenone Spirorenone Chemical structures of progesterone and spirolactones (steroid-17α-spirolactones).