Mexrenone

Mexrenone (code names ZK-32055, SC-25152) is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone that was never marketed.[1][2] It is the lactonic form of mexrenoic acid (mexrenoate), and mexrenoate potassium (SC-26714), the potassium salt of mexrenoic acid, also exists.[3] In addition to the mineralocorticoid receptor, mexrenone also binds to the glucocorticoid, androgen, and progesterone receptors.[4] Relative to spironolactone, it has markedly reduced antiandrogen activity (approximately one-tenth of the antimineralocorticoid dosage equivalent antiandrogen activity of spironolactone).[2] Eplerenone is the 9-11α-epoxy analogue of mexrenone.[5]

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
IUPAC name
  • methyl (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
Chemical and physical data
FormulaC24H32O5
Molar mass400.515 g·mol−1
3D model (JSmol)
SMILES
  • COC(=O)[C@@H]4C\C1=C\C(=O)CC[C@]1(C)[C@H]5CC[C@@]3(C)[C@@H](CC[C@]23CCC(=O)O2)[C@H]45
InChI
  • 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

See also

References
  1. Cutler, Gordon B.; Pita, Julio C.; Rifka, Safa M.; Menard, Raymond H.; Sauer, Mark A.; Loriaux, D. Lynn (1978). "SC 25152: A Potent Mineralocorticoid Antagonist with Reduced Affinity for the 5α-Dihydrotestosterone Receptor of Human and Rat Prostate". The Journal of Clinical Endocrinology & Metabolism. 47 (1): 171–175. doi:10.1210/jcem-47-1-171. ISSN 0021-972X. PMID 263288.
  2. Cutler GB, Sauer MA, Loriaux DL (1979). "SC 25152: a potent mineralocorticoid antagonist with decreased antiandrogenic activity relative to spironolactone". J. Pharmacol. Exp. Ther. 209 (1): 144–6. PMID 430374.
  3. Hofmann LM, Weier RM, Suleymanov OD, Pedrera HA (1977). "Mexrenoate potassium: a steroidal aldosterone antagonist and antihypertensive". J. Pharmacol. Exp. Ther. 201 (3): 762–8. PMID 864608.
  4. Gyorgy Szasz; Zsuzsanna Budvari-Barany (19 December 1990). Pharmaceutical Chemistry of Antihypertensive Agents. CRC Press. pp. 87–. ISBN 978-0-8493-4724-5.
  5. Ménard, Joël (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. ISSN 0303-7207. PMID 15134800. S2CID 19701784.



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