7α-Thiomethylspironolactone sulfoxide

{{Short description|Chemical compound}}

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| IUPAC_name = (7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-7-methylsulfinylspiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione

| image = 7α-Thiomethylspironolactone sulfoxide.svg

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| CAS_number_Ref = {{cascite|correct|CAS}}

| CAS_number = 38753-75-2

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| UNII = 59MB937W7X

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| PubChem = 162324

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| ChemSpiderID = 142538

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| ChEMBL = 3544706

| synonyms = 7α-TMS sulfoxide; 7α-Thiomethylspironolactone S-oxide; 7α-Methylsulfinylspironolactone

| C=23 | H=32 | O=4 | S=1

| SMILES = C[C@]12CCC(=O)C=C1C[C@H]([C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]45CCC(=O)O5)C)S(=O)C

| StdInChI_Ref =

| StdInChI = 1S/C23H32O4S/c1-21-8-4-15(24)12-14(21)13-18(28(3)26)20-16(21)5-9-22(2)17(20)6-10-23(22)11-7-19(25)27-23/h12,16-18,20H,4-11,13H2,1-3H3/t16-,17-,18+,20+,21-,22-,23+,28?/m0/s1

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| StdInChIKey = ADVFYBFTUKGFGC-FLWPULIFSA-N

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7α-Thiomethylspironolactone sulfoxide (also known as 7α-TMS sulfoxide, 7α-thiomethylspironolactone S-oxide, or 7α-methylsulfinylspironolactone) is a metabolite of spironolactone (brand name Aldactone), an antimineralocorticoid and antiandrogen medication.{{cite journal | vauthors = Cashman JR, Peña S | title = S-oxygenation of 7 alpha-thiomethylspironolactone by the flavin-containing monooxygenase | journal = Drug Metabolism and Drug Interactions | volume = 6 | issue = 3–4 | pages = 337–348 | date = 1988 | pmid = 3271645 | doi = 10.1515/dmdi.1988.6.3-4.337 | s2cid = 87034365 }}{{cite book| vauthors = Mohrke W, Ullrich F | chapter = Metabolism of Diuretics | veditors = Greger RF, Knauf H, Mutschler E |title=Diuretics | chapter-url = https://books.google.com/books?id=zhHpCAAAQBAJ&pg=PA194 |date=6 December 2012|publisher=Springer Science & Business Media|isbn=978-3-642-79565-7|pages=194–}}{{cite book| vauthors = Al-Hadiya BM, Belal F, Asiri YA, Gubara OA |title=Spironolactone|series=Analytical Profiles of Drug Substances and Excipients|volume=29|year=2002|pages=261–320|publisher=Academic Press |issn=1075-6280|doi=10.1016/S1075-6280(02)29009-6|isbn=9780122608292|url=https://books.google.com/books?id=RMN5zMW64ZEC&pg=PA310}}{{cite journal | vauthors = Abshagen U, Rennekamp H, Luszpinski G | title = Pharmacokinetics of spironolactone in man | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 296 | issue = 1 | pages = 37–45 | date = December 1976 | pmid = 1012347 | doi = 10.1007/BF00498838 | s2cid = 21225731 }}{{cite journal | vauthors = Overdiek HW, Merkus FW | title = The metabolism and biopharmaceutics of spironolactone in man | journal = Reviews on Drug Metabolism and Drug Interactions | volume = 5 | issue = 4 | pages = 273–302 | date = 1987 | pmid = 3333882 | doi = 10.1515/DMDI.1987.5.4.273 | s2cid = 29482256 }}{{cite journal | vauthors = Cashman JR, Peña S | title = Canrenone formation via general-base-catalyzed elimination of 7 alpha-(methylthio)spironolactone S-oxide | journal = Chemical Research in Toxicology | volume = 2 | issue = 2 | pages = 109–113 | date = 1989 | pmid = 2519709 | doi = 10.1021/tx00008a007 }} 7α-TMS sulfoxide is specifically formed from 7α-thiomethylspironolactone (7α-TMS).