6β-Hydroxy-7α-thiomethylspironolactone (6β-OH-7α-TMS) is a steroidal antimineralocorticoid of the spirolactone group and a major active metabolite of spironolactone. Other important metabolites of spironolactone include 7α-thiospironolactone (7α-TS; SC-24813), 7α-thiomethylspironolactone (7α-TMS; SC-26519), 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.

6β-Hydroxytestosterone, which is analogous to 6β-OH-7α-TMS, has been found to possess virtually no androgenicity.

See also

  • 7α-Thioprogesterone

References

Further reading

  • 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.



RCSB PDB 6TTN Nterminally truncated hyoscyamine 6hydroxylase (tH6H

7(6acetyloxy8hydroxy4a,7dimethyl5'methylidene2',4,4

6Chloro9[2α(hydroxymethyl)3α,6βdihydroxyoxepane4βyl]9Hpurine

(7s,9s)6,9,11Trihydroxy9(2hydroxyacetyl)7[(6s)5hydroxy6

6βhydroxyl7epiloganin CAS 125410288