|Other names||7α-TMS; SC-26519; 17α-Hydroxy-7α-(methylthio)-3-oxopregn-4-ene-21-carboxylic acid γ-lactone|
|Chemical and physical data|
|Molar mass||388.57 g·mol−1|
|3D model (JSmol)|
7α-Thiomethylspironolactone (7α-TMS; developmental code name SC-26519) is a steroidal antimineralocorticoid and antiandrogen of the spirolactone group and the major active metabolite of spironolactone. Other important metabolites of spironolactone include 7α-thiospironolactone (7α-TS; SC-24813), 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).
|Compound||Cmax (day 1)||Cmax (day 15)||AUC (day 15)||t1/2|
|Spironolactone||72 ng/mL (173 nmol/L)||80 ng/mL (192 nmol/L)||231 ng•hour/mL (555 nmol•hour/L)||1.4 hours|
|Canrenone||155 ng/mL (455 nmol/L)||181 ng/mL (532 nmol/L)||2,173 ng•hour/mL (6,382 nmol•hour/L)||16.5 hours|
|7α-TMS||359 ng/mL (924 nmol/L)||391 ng/mL (1,006 nmol/L)||2,804 ng•hour/mL (7,216 nmol•hour/L)||13.8 hours|
|6β-OH-7α-TMS||101 ng/mL (250 nmol/L)||125 ng/mL (309 nmol/L)||1,727 ng•hour/mL (4,269 nmol•hour/L)||15.0 hours|
|Sources: See template.|
7α-TMS has been found to account for around 80% of the potassium-sparing effect of spironolactone, whereas canrenone accounts for the remaining approximate 10 to 25% of the potassium-sparing effect of the drug.
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