7α-Thiomethylspironolactone

7α-TMS
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.wikipedia
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7α-Thiospironolactone

Other important metabolites of spironolactone include 7α-thiospironolactone (7α-TS; SC-24813), 6β-hydroxy-7α-thiomethylspironolactone (6β-OH-7α-TMS), and canrenone (SC-9376).
Other important metabolites of spironolactone include 7α-thiomethylspironolactone (7α-TMS; SC-26519), 6β-hydroxy-7α-thiomethylspironolactone (6β-OH-7α-TMS), and canrenone (SC-9376).

Spirolactone

17α-Spirolactone
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.
Spirolactones that were not ever marketed include SC-5233, SC-8109, SC-11927 (Catatoxic Steroid 1; CS-1), spiroxasone, prorenone (SC-23133), prorenoate potassium (SC-23992), 7α-thiospironolactone (SC-24813), mexrenone (SC-25152, ZK-32055), dicirenone (SC-26304), 7α-thiomethylspironolactone (SC-26519), mexrenoate potassium (SC-26714), spirorenone (ZK-35973), ZK-91587 (15β,16β-methylenemexrenone), mespirenone (ZK-94679), and ZK-97894 (7α-thiomethylmespirenone).

Spironolactone

AldactoneAldactazideSpironalactone
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.
The major active forms of spironolactone are 7α-thiomethylspironolactone (7α-TMS) and canrenone (7α-desthioacetyl-δ 6 -spironolactone).

6β-Hydroxy-7α-thiomethylspironolactone

6β-OH-7α-TMS
Other important metabolites of spironolactone include 7α-thiospironolactone (7α-TS; SC-24813), 6β-hydroxy-7α-thiomethylspironolactone (6β-OH-7α-TMS), and canrenone (SC-9376).
Other important metabolites of spironolactone include 7α-thiospironolactone (7α-TS; SC-24813), 7α-thiomethylspironolactone (7α-TMS; SC-26519), and canrenone (SC-9376).

Canrenone

Other important metabolites of spironolactone include 7α-thiospironolactone (7α-TS; SC-24813), 6β-hydroxy-7α-thiomethylspironolactone (6β-OH-7α-TMS), and canrenone (SC-9376).
It has been found to account for approximately 10 to 25% of the potassium-sparing effect of spironolactone, whereas another metabolite, 7α-thiomethylspironolactone (7α-TMS), accounts for around 80% of the potassium-sparing effect of the drug.

7α-Thioprogesterone

TP4
As an antiandrogen, 7α-TP4 has approximately 8.5% of the affinity of dihydrotestosterone (DHT) for the rat ventral prostate androgen receptor (AR), which is similar to that of spironolactone and its active metabolite 7α-thiomethylspironolactone.

7α-Thiomethylspironolactone sulfoxide

7α-TMS sulfoxide is specifically formed from 7α-thiomethylspironolactone (7α-TMS).

Steroid

steroidssteroidogenesisbiosynthesis of steroids
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.

Antimineralocorticoid

aldosterone antagonistaldosterone antagonistsmineralocorticoid antagonist
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.

Antiandrogen

antiandrogensandrogen synthesis inhibitoranti-androgen
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.

Active metabolite

active metabolitesactiveactive drug
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.

Metabolite

metabolitesactive metabolitebreakdown product
Other important metabolites of spironolactone include 7α-thiospironolactone (7α-TS; SC-24813), 6β-hydroxy-7α-thiomethylspironolactone (6β-OH-7α-TMS), and canrenone (SC-9376).

Prodrug

pro-drugprodrugsinactive prodrug
Spironolactone is a prodrug with a short terminal half-life of 1.4 hours.

Biological half-life

elimination half-lifehalf-lifeterminal half-life
Spironolactone is a prodrug with a short terminal half-life of 1.4 hours.

Ligand (biochemistry)

affinityligandbinding affinity
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.

Prostate

prostate glandprostaticventral prostate
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.

Androgen receptor

androgen receptorsARandrogen
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.

Dihydrotestosterone

5α-DihydrotestosteroneDHT17-hydroxyandrostan-3-one
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).

Potassium-sparing diuretic

potassium-sparingpotassium-sparing diureticspotassium sparing diuretic
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.

Pharmacodynamics of spironolactone

The major active forms of spironolactone include 7α-thiomethylspironolactone (7α-TMS) and canrenone (7α-desthioacetyl-δ 6 -spironolactone), while more minor metabolites of spironolactone include 7α-thiospironolactone (7α-TS), 6β-hydroxy-7α-thiomethylspironolactone (6β-OH-7α-TMS), and a number of others.