Spiroxasone

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	6673-97-8
PubChem CID	23141
ChemSpider	21652
UNII	8P0U2ZA1NQ
KEGG	D05912
ChEMBL	ChEMBL2105514
CompTox Dashboard (EPA)	DTXSID101024404
Chemical and physical data
Formula	C24H34O3S
Molar mass	402.59 g·mol−1
3D model (JSmol)	Interactive image
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

Spiroxasone (INN Tooltip International Nonproprietary Name, USAN Tooltip United States Adopted Name) 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]}

References

1. Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1114–. ISBN   978-1-4757-2085-3.
2. Morton IK, Hall JM (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 (November 1972). "Antiandrogens. 2',3' -Tetrahydrofuran-2'spiro-17-(1,2 -methylene-4-androsten-3-ones)". Journal of Medicinal Chemistry. 15 (11): 1165–1168. doi:10.1021/jm00281a018. PMID   4654667.