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7α-Thiospironolactone
| Column 1 |
|---|
| 7α-TS; SC-24813; Deacetylspironolactone; Mercaptospironolactone; 17α-Hydroxy-7α-mercapto-3-oxopregn-4-ene-21-carboxylic acid γ-lactone |
| Antimineralocorticoid; Antiandrogen |
| IUPAC name |
| (7R,8R,9S,10R,13S,14S,17R)-10,13-Dimethyl-7-sulfanylspiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione |
| .mw-parser-output .plainlist ol,.mw-parser-output .plainlist ul{line-height:inherit;list-style:none;margin:0;padding:0}.mw-parser-output .plainlist ol li,.mw-parser-output .plainlist ul li{margin-bottom:0}38753-76-3 |
| 119472 |
| 58817151 |
| 4LH70U7H4Z |
| ChEMBL3544689 |
| DTXSID20959566 |
| C22H30O3S |
| 374.54 g·mol−1 |
| Interactive image |
| SMILES |
| C[C@]12CCC(=O)C=C1CC@HS |
| InChI |
| InChI=1S/C22H30O3S/c1-20-7-3-14(23)11-13(20)12-17(26)19-15(20)4-8-21(2)16(19)5-9-22(21)10-6-18(24)25-22/h11,15-17,19,26H,3-10,12H2,1-2H3/t15-,16-,17+,19+,20-,21-,22+/m0/s1Key:NZCDWYJROUPYPT-NYTLBARGSA-N |
7α-Thiospironolactone (7α-TS; developmental code name SC-24813; also known as deacetylspironolactone) is a steroidal antimineralocorticoid and antiandrogen of the spirolactone group and a minor active metabolite of spironolactone. Other important metabolites of spironolactone include 7α-thiomethylspironolactone (7α-TMS; SC-26519), 6β-hydroxy-7α-thiomethylspironolactone (6β-OH-7α-TMS), and canrenone (SC-9376).
Spironolactone is a prodrug with a short terminal half-life of 1.4 hours. The active metabolites of spironolactone have extended terminal half-lives of 13.8 hours for 7α-TMS, 15.0 hours for 6β-OH-7α-TMS, and 16.5 hours for canrenone, and accordingly, these metabolites are responsible for the therapeutic effects of the drug.
7α-TS and 7α-TMS have been found to possess approximately equivalent affinity for the rat ventral prostate androgen receptor (AR) relative to that of spironolactone. The affinity of 7α-TS, 7α-TMS, and spironolactone for the rat prostate AR is about 3.0 to 8.5% of that of dihydrotestosterone (DHT).
7α-TS, via a reactive metabolite formed by 17α-hydroxylase, is a suicide inhibitor of 17α-hydroxylase, and is thought to be involved in the inhibition of 17α-hydroxylase by spironolactone.
| Compound | Cmax (ng/mL)(day 1) | Cmax (ng/mL)(day 15) | AUC (ng•hr/ml)(day 15) | t1/2 (hr) |
|---|---|---|---|---|
| Spironolactone | 72 | 80 | 231 | 1.4 |
| Canrenone | 155 | 181 | 2173 | 16.5 |
| 7α-TMSTooltip 7α-Thiomethylspironolactone | 359 | 391 | 2804 | 13.8 |
| 6β-OH-7α-TMSTooltip 6β-Hydroxy-7α-thiomethylspironolactone | 101 | 125 | 1727 | 15.0 |
A study assessed the interaction of spironolactone and 7α-TS with sex hormone-binding globulin and found that they had very low affinity for this carrier protein.
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7α-Thioprogesterone
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Gardiner P, Schrode K, Quinlan D, Martin BK, Boreham DR, Rogers MS, Stubbs K, Smith M, Karim A (1989). "Spironolactone metabolism: steady-state serum levels of the sulfur-containing metabolites". J Clin Pharmacol. 29 (4): 342–7. doi:10.1002/j.1552-4604.1989.tb03339.x. PMID 2723123. S2CID 29457093.
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