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| Clinical data | |
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| 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 |
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| ECHA InfoCard | 100.012.321 |
| Chemical and physical data | |
| Formula | C22H30O3 |
| Molar mass | 342.479 g·mol−1 |
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SC-5233, also known as6,7-dihydrocanrenone or20-spirox-4-ene-3,20-dione, is asynthetic,steroidalantimineralocorticoid of thespirolactone group which was developed byG. D. Searle & Company in the 1950s but was never marketed.[1][2] It was the first syntheticantagonist of themineralocorticoid receptor to have been identified and tested in humans.[1][3] The drug was found to lack appreciable oralbioavailability and to be of lowpotency when administeredparenterally,[4] but it nonetheless produced a milddiuretic effect in patients withcongestive 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]
SC-5233 is thepropionic acidlactone oftestosterone (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 unsubstitutedparent orprototype compound of the spirolactone family of steroidal antimineralocorticoids.[2][8]
Similarly to other spirolactones like canrenone and spironolactone, SC-5233 has someantiandrogenic activity and antagonizes the effects oftestosterone in animals.[7] In addition, along with SC-8109, it has been found to possess potentprogestogenic activity.[9]
Chemical structures ofspirolactones |
Cena and Kagawa first synthesized 3-(3-oxo-17β-hydroxy-4-androsten-17α-yl)-propionic acid-gamma-lactone and later prepared its 19-nor analogue. These compounds were designated SC-5233 and SC-8109, respectively. Both have anti-aldosterone activity and most of the early work on aldosterone antagonism was done with their aid. SC-5233 is not appreciably absorbed when given by mouth and the parenteral dose is large. As in the case of certain other steroids the 19-nor derivative was an improvement on the parent compound (Klyne, 1959). SC-8109 is well absorbed from the alimentary tract, but the dose is about 2 g daily.
[SC-5233] (total dose of 5 mg/rat) partially blocked the effects of testosterone propionate on the seminal vesicles and prostate in similar animals.
