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Human drug metabolites
6β-Hydroxy-7α-thiomethylspironolactone
Другие языки:

    6β-Hydroxy-7α-thiomethylspironolactone

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    6β-Hydroxy-7α-thiomethylspironolactone
    6β-Hydroxy-7α-thiomethylspironolactone.svg
    Clinical data
    Other names 6β-OH-7α-TMS; 6β,17α-Dihydroxy-7α-(methylthio)-3-oxo-pregn-4-ene-21-carboxylic acid γ-lactone
    Drug class Antimineralocorticoid
    Identifiers
    • (6S,7S,8R,10R,13S,14S,17R)-6-hydroxy-10,13-dimethyl-7-methylsulfanylspiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione
    CAS Number
    PubChem CID
    ChemSpider
    UNII
    Chemical and physical data
    Formula C23H32O4S
    Molar mass 404.57 g·mol−1
    3D model (JSmol)
    • CS[C@@H]1[C@@H](O)C2=CC(=O)CC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC[C@@]45CCC(=O)O5)[C@H]13
    • InChI=1S/C23H32O4S/c1-21-8-4-13(24)12-16(21)19(26)20(28-3)18-14(21)5-9-22(2)15(18)6-10-23(22)11-7-17(25)27-23/h12,14-15,18-20,26H,4-11H2,1-3H3/t14-,15-,18+,19-,20-,21+,22-,23+/m0/s1
    • Key:NWLBSWATTSRBOV-DFSNYPBXSA-N

    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.

    Pharmacokinetics of 100 mg/day spironolactone and its metabolites
    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.

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

    See also

    Further reading



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