SC-8109 is a steroidal antimineralocorticoid of the spirolactone group which was never marketed.[1][2] It is a potent antagonist of the mineralocorticoid receptor and is more potent than the related drug SC-5233 (of which SC-8109 is the 19-nor analogue).[1][3] However, SC-8109 was found to have relatively low oral bioavailability and potency,[1][4] though it nonetheless produced a mild diuretic effect in patients with congestive heart failure.[2] Spironolactone (SC-9420; Aldactone), another spirolactone, followed and had both good oral bioavailability and potency, and was the first antimineralocorticoid to be marketed.[1][5]
Quick facts Clinical data, Other names ...
SC-8109 |
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| Other names | 19-Norspirolactone; 19-Nor-17α-(2-carboxyethyl)testosterone γ-lactone; 3-Oxo-17β-hydroxyestr-4-ene-17-propanoic acid lactone; 17-Hydroxy-3-oxo-19-Nor-17α-pregn-4-ene-21-carboxylic acid γ-lactone |
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(8R,9S,10R,13S,14S,17R)-13-Methylspiro[1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione
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| Formula | C21H28O3 |
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| Molar mass | 328.452 g·mol−1 |
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C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@]24CCC(=O)O4)CCC5=CC(=O)CC[C@H]35
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InChI=1S/C21H28O3/c1-20-9-6-16-15-5-3-14(22)12-13(15)2-4-17(16)18(20)7-10-21(20)11-8-19(23)24-21/h12,15-18H,2-11H2,1H3/t15-,16+,17+,18-,20-,21+/m0/s1 Key:CXXAIOQMCGJVHT-XUJOMZSTSA-N
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In addition to its antimineralocorticoid activity, SC-8109 shows potent progestogenic activity, with similar potency relative to that of progesterone.[6] Its analogue, SC-5233, possesses similar but less potent progestogenic activity.[6] In addition, SC-5233 has been assessed and found to possess some antiandrogenic activity, antagonizing the effects of testosterone in animals, and SC-8109 may as well.[7]
More information Compound, PRTooltip Progesterone receptor ...
Relative affinities (%) of SC-8109 and related steroids[8]
| Compound | PRTooltip Progesterone receptor | ARTooltip Androgen receptor | ERTooltip Estrogen receptor | GRTooltip Glucocorticoid receptor | MRTooltip Mineralocorticoid receptor | SHBGTooltip Sex hormone-binding globulin | CBGTooltip Corticosteroid binding globulin |
| Progesterone | 100 | 3–10 | <1 | <1 | 3–10 | ? | ? |
| SC-8109 | 191 | 25–50 | <1 | <1 | 15–25 | ? | ? |
| Values are percentages (%). Reference ligands (100%) were progesterone for the PRTooltip progesterone receptor, testosterone for the ARTooltip androgen receptor, estradiol for the ERTooltip estrogen receptor, DEXATooltip dexamethasone for the GRTooltip glucocorticoid receptor, and aldosterone for the MRTooltip mineralocorticoid receptor. |
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