SC-5233

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.^[1][2] It was the first synthetic antagonist of the mineralocorticoid receptor to have been identified and tested in humans.^[1][3] The drug was found to lack appreciable oral bioavailability and to be of low potency when administered parenterally,^[4] but it nonetheless produced a mild diuretic effect in patients with congestive heart failure.^[1] SC-8109, the 19-nor (19-demethyl) analogue, was developed and found to have improved oral bioavailability and potency, but still had low potency.^[5] Spironolactone (SC-9420; Aldactone) followed and had both good oral bioavailability and potency, and was the first synthetic antimineralocorticoid to be marketed.^[3] It has about 46-fold higher oral potency than SC-5233.^[6]

Other names6,7-Dihydrocanrenone; 7-Desthioacetylspironolactone; 20-Spirox-4-ene-3,20-dione

Routes of
administrationBy mouth

Drug classAntimineralocorticoid; Progestogen; Steroidal antiandrogen

ATC code

• None

Quick facts Clinical data, Other names ...

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

Close

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.^[7] It is the unsubstituted parent or prototype compound of the spirolactone family of steroidal antimineralocorticoids.^[2][8]

Similarly to other spirolactones like canrenone and spironolactone, SC-5233 has some antiandrogenic activity and antagonizes the effects of testosterone in animals.^[7] In addition, along with SC-8109, it has been found to possess potent progestogenic activity.^[9]

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