SC-5233

SC-5233
Clinical data

Routes of administration	Oral
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
Synonyms	7-Desthioacetylspironolactone
CAS Number	976-70-5
PubChem CID	101931
ChemSpider	92091
ChEMBL	CHEMBL400534
Chemical and physical data
Formula	C₂₂H₃₀O₃
Molar mass	342.4718 g/mol
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 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 propionic acid lactone of 17β-hydroxyandrost-4-en-3-one or testosterone 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 antiandrogen activity and antagonizes the effects of testosterone in animals. In addition, along with SC-8109, it has been found to possess potent progestogenic activity.

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