Dicirenone

Dicirenone (INN, USAN; developmental code name SC-26304; also known as 7α-carboxyisopropylspirolactone) 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 1974.[1] Similarly to other spirolactones like spironolactone, dicirenone also possesses antiandrogen activity, albeit with relatively reduced affinity.[3]

Dicirenone
Clinical data
Other namesSC-26304; 7α-Carboxyisopropylspirolactone; 17α-Hydroxy-3-oxopregn-4-ene-7α,21-dicarboxylic acid γ-lactone 1-isopropyl ester
Routes of
administration		Oral
Identifiers
IUPAC name
  • Propan-2-yl (7R,8R,9S,10R,13S,14S,17R)-10,13-Dimethyl-3,5'-dioxospiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,2'-oxolane]-7-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC26H36O5
Molar mass428.569 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)OC(=O)[C@@H]1CC2=CC(=O)CC[C@@]2([C@@H]3[C@@H]1[C@@H]4CC[C@]5([C@]4(CC3)C)CCC(=O)O5)C
InChI
  • InChI=1S/C26H36O5/c1-15(2)30-23(29)18-14-16-13-17(27)5-9-24(16,3)19-6-10-25(4)20(22(18)19)7-11-26(25)12-8-21(28)31-26/h13,15,18-20,22H,5-12,14H2,1-4H3/t18-,19+,20+,22-,24+,25+,26-/m1/s1
  • Key:WUVPAYPBMZMHJO-IMNLCBETSA-N

References
  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 387–. 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. 97–. ISBN 978-94-011-4439-1.
  3. Netchitailo P, Delarue C, Perroteau I, Leboulenger F, Capron MH, Vaudry H (1985). "Relative inhibitory potency of five mineralocorticoid antagonists on aldosterone biosynthesis in vitro". Biochem. Pharmacol. 34 (2): 189–94. doi:10.1016/0006-2952(85)90123-6. PMID 2981534.



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