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(Top) 1 Chemistry 1.1 Synthesis 2 See also 3 References

Prorenone

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Prorenone
Clinical data

Other names	SC-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	49848-04-6
PubChem CID	170819
IUPHAR/BPS	2876
ChemSpider	149344
CompTox Dashboard (EPA)	DTXSID50964446
Chemical and physical data
Formula	C₂₃H₃₀O₃
Molar mass	354.490 g·mol⁻¹
3D model (JSmol)	Interactive image
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 inhibitorofaldosterone biosynthesis.^[4]

Chemistry[edit]

Synthesis[edit]

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

References[edit]

^ ^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.

^ Szasz G, Budvari-Barany Z (19 December 1990). Pharmaceutical Chemistry of Antihypertensive Agents. CRC Press. pp. 87–. ISBN 978-0-8493-4724-5.

^ ^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.

^ 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.

^ 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.