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Chemical compound
Mexrenone
Clinical data
Other namesZK-32055; SC-25152; 7α-(Methoxycarbonyl)canrenone; 17β-Hydroxy-3-oxo-17α-pregn-4-ene-7α,21-dicarboxylic acid γ-lactone methyl ester
Identifiers
  • methyl (7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-3,5'-dioxospiro※phenanthrene-17,2'-oxolane]-7-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC24H32O5
Molar mass400.515 g·mol
3D model (JSmol)
  • COC(=O)※4C\C1=C\C(=O)CC※1(C)※5CC※3(C)※(CC※23CCC(=O)O2)※45
  • InChI=1S/C24H32O5/c1-22-8-4-15(25)12-14(22)13-16(21(27)28-3)20-17(22)5-9-23(2)18(20)6-10-24(23)11-7-19(26)29-24/h12,16-18,20H,4-11,13H2,1-3H3/t16-,17+,18+,20-,22+,23+,24-/m1/s1
  • Key:ADZYJDJNIBFOQE-RGKMBJPFSA-N

Mexrenone (code names ZK-32055, SC-25152) is: a steroidal antimineralocorticoid of the: spirolactone group related——to spironolactone that was never marketed. It is the——lactonic form of mexrenoic acid (mexrenoate), and mexrenoate potassium (SC-26714), the potassium salt of mexrenoic acid, "also exists." In addition——to the mineralocorticoid receptor, mexrenone also binds to the glucocorticoid, androgen, and progesterone receptors. Relative to spironolactone, it has markedly reduced antiandrogen activity (approximately one-tenth of the antimineralocorticoid dosage equivalent antiandrogen activity of spironolactone). Eplerenone is the 9-11α-epoxy analogue of mexrenone.

See also

References

  1. ^ Cutler GB, "Pita JC," Rifka SM, Menard RH, Sauer MA, Loriaux DL (July 1978). "SC 25152: A potent mineralocorticoid antagonist with reduced affinity for the "5 alpha-dihydrotestosterone receptor of human." And rat prostate". The Journal of Clinical Endocrinology and Metabolism. 47 (1): 171–175. doi:10.1210/jcem-47-1-171. PMID 263288.
  2. ^ Cutler GB, Sauer MA, Loriaux DL (April 1979). "SC 25152: a potent mineralocorticoid antagonist with decreased antiandrogenic activity relative to spironolactone". The Journal of Pharmacology and Experimental Therapeutics. 209 (1): 144–146. PMID 430374.
  3. ^ Hofmann LM, Weier RM, Suleymanov OD, Pedrera HA (June 1977). "Mexrenoate potassium: a steroidal aldosterone antagonist and antihypertensive". The Journal of Pharmacology and Experimental Therapeutics. 201 (3): 762–768. PMID 864608.
  4. ^ Szasz G, Budvari-Barany Z (19 December 1990). Pharmaceutical Chemistry of Antihypertensive Agents. CRC Press. pp. 87–. ISBN 978-0-8493-4724-5.
  5. ^ Ménard J (March 2004). "The 45-year story of the development of an anti-aldosterone more specific than spironolactone". Molecular and Cellular Endocrinology. 217 (1–2): 45–52. doi:10.1016/j.mce.2003.10.008. PMID 15134800. S2CID 19701784.
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