Spiroxasone

Spiroxasone (INN, USAN) is a synthetic, steroidal antimineralocorticoid of the spirolactone group which was developed as a diuretic and antihypertensive agent but was never marketed.[1][2] It was synthesized and assayed in 1963.[1] The drug is 7α-acetylthiospirolactone with the ketone group removed from the C17α spirolactone ring.[1] Similarly to other spirolactones like spironolactone, spiroxasone also possesses antiandrogen activity.[3][4]

Spiroxasone
Clinical data
Routes of
administration		By mouth
Identifiers
IUPAC name
  • S-[(7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3-oxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-yl] ethanethioate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC24H34O3S
Molar mass402.59 g·mol−1
3D model (JSmol)
SMILES
  • CC(=O)S[C@@H]1CC2=CC(=O)CC[C@@]2([C@@H]3[C@@H]1[C@@H]4CC[C@]5([C@]4(CC3)C)CCCO5)C
InChI
  • InChI=1S/C24H34O3S/c1-15(25)28-20-14-16-13-17(26)5-9-22(16,2)18-6-10-23(3)19(21(18)20)7-11-24(23)8-4-12-27-24/h13,18-21H,4-12,14H2,1-3H3/t18-,19-,20+,21+,22-,23-,24-/m0/s1
  • Key:XKCGICBTWRNUCL-KIEAKMPYSA-N

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1114–. ISBN 978-1-4757-2085-3.
  2. I.K. Morton; Judith M. Hall (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 261–. ISBN 978-94-011-4439-1.
  3. Progress in Medicinal Chemistry. Elsevier. 1 January 1979. pp. 69–. ISBN 978-0-08-086264-4. Spiroxasone [...] is also an anti-androgen [379].
  4. Rasmusson GH, Chen A, Reynolds GF, Patanelli DJ, Patchett AA, Arth GE (1972). "Antiandrogens. 2',3' -Tetrahydrofuran-2'spiro-17-(1,2 -methylene-4-androsten-3-ones)". J. Med. Chem. 15 (11): 1165–8. doi:10.1021/jm00281a018. PMID 4654667.



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