Prorenone

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
IUPAC name
  • (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-spiro[cyclopenta[a]cyclopropa[l]phenanthrene-8,2'-furan]-3,5'-dione
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H30O3
Molar mass354.490 g·mol−1
3D model (JSmol)
SMILES
  • O=C6O[C@@]5([C@@]3([C@H]([C@@H]2[C@H]4[C@@H](/C1=C/C(=O)CC[C@]1(C)[C@H]2CC3)C4)CC5)C)CC6
InChI
  • 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 trimethylsulfonium iodide and sodium hydride.[5]

See also

References

  1. 1 2 3 Claire, M.; Rafestin-Oblin, M. E.; Michaud, A.; Roth-Meyer, C.; Corvol, P. (1979). "Mechanism of Action of a New Antialdosterone Compound, Prorenone*". Endocrinology. 104 (4): 1194–1200. doi:10.1210/endo-104-4-1194. ISSN 0013-7227. PMID 436757.
  2. ↑ Gyorgy Szasz; Zsuzsanna Budvari-Barany (19 December 1990). Pharmaceutical Chemistry of Antihypertensive Agents. CRC Press. pp. 87–. ISBN 978-0-8493-4724-5.
  3. 1 2 Kamata S, Matsui T, Haga N, Nakamura M, Odaguchi K, Itoh T, Shimizu T, Suzuki T, Ishibashi M, Yamada F (September 1987). "Aldosterone antagonists. 2. Synthesis and biological activities of 11,12-dehydropregnane derivatives". J. Med. Chem. 30 (9): 1647–58. doi:10.1021/jm00392a022. PMID 3040999.
  4. ↑ Netchitailo, Pierre; Delarue, Catherine; Perroteau, Isabelle; Leboulenger, Francois; Capron, Michel-Hubert; Vaudry, Hubert (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. ISSN 0006-2952. PMID 2981534.
  5. ↑ Chinn, L.; 1974, U.S. Patent 3,845,041



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