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. It was synthesized and assayed in 1974. Similarly to other spirolactones like spironolactone, dicirenone also possesses antiandrogen activity, albeit with relatively reduced affinity.

Chemical compound

Pharmaceutical compound

Dicirenone

Clinical data
Other names	SC-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	41020-79-5
PubChem CID	10387872
ChemSpider	8563314
UNII	M8K306YKSX
KEGG	D03792
ChEMBL	ChEMBL2106258
CompTox Dashboard (EPA)	DTXSID101023456
Chemical and physical data
Formula	C26H36O5
Molar mass	428.569 g·mol−1
3D model (JSmol)	Interactive image
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

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]

References

[edit]

1. ^ ^{a b} Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 387–. 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. 97–. ISBN 978-94-011-4439-1.
3. ^ Netchitailo P, Delarue C, Perroteau I, Leboulenger F, Capron MH, Vaudry H (January 1985). "Relative inhibitory potency of five mineralocorticoid antagonists on aldosterone biosynthesis in vitro". Biochemical Pharmacology. 34 (2): 189–194. doi:10.1016/0006-2952(85)90123-6. PMID 2981534.

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