Prorenone

In this article we are going to explore the fascinating world of Prorenone. From its origins to its impact on today's society, Prorenone has played a crucial role in different aspects of daily life. Throughout history, Prorenone has evolved and adapted to the changing needs and demands of society, becoming a topic of great relevance today. Through this article, we will seek to understand the importance and meaning of Prorenone, as well as its influence in various areas.
Prorenone
Clinical data
Other namesSC-23133; 3-(17β-Hydroxy-6β,7β-methylene-3-oxo-4-androsten-17α-yl)propionic acid γ-lactone
ATC code
  • None
Identifiers
  • (1aS,5aR,5bS,7aS,8R,10aS,10bR,10cS)-5a,7a-Dimethyl-1,1a,3',4,4',5,5a,5b,6,7,7a,9,10,10a,10b,10c-hexadecahydro-3H,5'H-spirocyclopropaphenanthrene-8,2'-furan]-3,5'-dione
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H30O3
Molar mass354.490 g·mol−1
3D model (JSmol)
  • O=C6O5(3((24(/C1=C/C(=O)CC1(C)2CC3)C4)CC5)C)CC6
  • InChI=1S/C23H30O3/c1-21-7-3-13(24)11-18(21)14-12-15(14)20-16(21)4-8-22(2)17(20)5-9-23(22)10-6-19(25)26-23/h11,14-17,20H,3-10,12H2,1-2H3/t14-,15+,16-,17-,20+,21+,22-,23+/m0/s1
  • Key:RRHHMFQGHCFGMH-LAPLKBAYSA-N

Prorenone (developmental code name SC-23133) is a steroidal antimineralocorticoid of the spirolactone group related to spironolactone that was never marketed.[1] It is the lactonic form of prorenoic acid (prorenoate), and prorenoate potassium (SC-23992), the potassium salt of prorenoic acid, also exists.[1] Prorenoate potassium is about 8 times more potent than spironolactone as an antimineralocorticoid in animals, and it may act as a prodrug to prorenone.[1] In addition to the mineralocorticoid receptor, prorenone also binds to the glucocorticoid, androgen, and progesterone receptors.[2][3] The antiandrogenic potency of prorenone in vivo in animals is close to that of spironolactone.[3] Similarly to spironolactone, prorenone is also a potent inhibitor of aldosterone biosynthesis.[4]

Chemistry

Synthesis

Prorenone can be synthesized via a Johnson–Corey–Chaykovsky reaction by reaction of canrenone with trimethylsulfoxonium iodide and sodium hydride.[5]

See also

References

  1. ^ a b c Claire M, Rafestin-Oblin ME, Michaud A, Roth-Meyer C, Corvol P (April 1979). "Mechanism of action of a new antialdosterone compound, prorenone". Endocrinology. 104 (4): 1194–1200. doi:10.1210/endo-104-4-1194. PMID 436757.
  2. ^ Szasz G, Budvari-Barany Z (19 December 1990). Pharmaceutical Chemistry of Antihypertensive Agents. CRC Press. pp. 87–. ISBN 978-0-8493-4724-5.
  3. ^ a b Kamata S, Matsui T, Haga N, Nakamura M, Odaguchi K, Itoh T, et al. (September 1987). "Aldosterone antagonists. 2. Synthesis and biological activities of 11,12-dehydropregnane derivatives". Journal of Medicinal Chemistry. 30 (9): 1647–1658. doi:10.1021/jm00392a022. PMID 3040999.
  4. ^ 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.
  5. ^ US 3845041, Chinn L, "7-Halomethyl-17-hydroxy-3-oxo-17alpha-pregn-4-ene-21-carboxylic acid gamma-lactones", issued 19 October 1974, assigned to GD Searle LLC. 
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