7α-Thiomethylspironolactone sulfoxide

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.[1][2][3][4][5][6] 7α-TMS sulfoxide is specifically formed from 7α-thiomethylspironolactone (7α-TMS).[1][2][4][3][5][6]

7α-Thiomethylspironolactone sulfoxide
Clinical data
Other names7α-TMS sulfoxide; 7α-Thiomethylspironolactone S-oxide; 7α-Methylsulfinylspironolactone
Identifiers
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
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H32O4S
Molar mass404.57 g·mol−1
3D model (JSmol)
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
InChI
  • InChI=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
  • Key:ADVFYBFTUKGFGC-FLWPULIFSA-N

References
  1. Cashman JR, Peña S (1988). "S-oxygenation of 7 alpha-thiomethylspironolactone by the flavin-containing monooxygenase". Drug Metabol Drug Interact. 6 (3–4): 337–48. doi:10.1515/dmdi.1988.6.3-4.337. PMID 3271645. S2CID 87034365.
  2. Rainer F. Greger; H. Knauf; E. Mutschler (6 December 2012). Diuretics. Springer Science & Business Media. pp. 194–. ISBN 978-3-642-79565-7.
  3. Al-Hadiya, Badraddin M.H.; Belal, Fathalla; Asiri, Yousif A.; Gubara, Othman A. (2002). Spironolactone. Analytical Profiles of Drug Substances and Excipients. Vol. 29. pp. 261–320. doi:10.1016/S1075-6280(02)29009-6. ISBN 9780122608292. ISSN 1075-6280.
  4. Abshagen, U.; Rennekamp, H.; Luszpinski, G. (1976). "Pharmacokinetics of spironolactone in man". Naunyn-Schmiedeberg's Archives of Pharmacology. 296 (1): 37–45. doi:10.1007/BF00498838. ISSN 0028-1298. PMID 1012347. S2CID 21225731.
  5. Overdiek HW, Merkus FW (1987). "The metabolism and biopharmaceutics of spironolactone in man". Rev Drug Metab Drug Interact. 5 (4): 273–302. doi:10.1515/DMDI.1987.5.4.273. PMID 3333882. S2CID 29482256.
  6. Cashman JR, Peña S (1989). "Canrenone formation via general-base-catalyzed elimination of 7 alpha-(methylthio)spironolactone S-oxide". Chem. Res. Toxicol. 2 (2): 109–13. doi:10.1021/tx00008a007. PMID 2519709.


This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.