Movatterモバイル変換

[0]ホーム
URL:

Jump to content
WikipediaThe Free Encyclopedia
Search

Prorenone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
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-spiro[cyclopenta[a]cyclopropa[l]phenanthrene-8,2'-furan]-3,5'-dione
CAS Number
PubChemCID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC23H30O3
Molar mass354.490 g·mol−1
3D model (JSmol)
  • 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=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 nameSC-23133) is asteroidalantimineralocorticoid of thespirolactone group related tospironolactone that was never marketed.[1] It is thelactonic form ofprorenoic acid (prorenoate), andprorenoate potassium (SC-23992), thepotassiumsalt of prorenoic acid, also exists.[1] Prorenoate potassium is about 8 times morepotent than spironolactone as an antimineralocorticoid in animals, and it may act as aprodrug to prorenone.[1] In addition to themineralocorticoid receptor, prorenone also binds to theglucocorticoid,androgen, andprogesterone receptors.[2][3] The antiandrogenic potency of prorenonein vivo in animals is close to that of spironolactone.[3] Similarly to spironolactone, prorenone is also a potentinhibitor ofaldosteronebiosynthesis.[4]

Chemistry

[edit]

Synthesis

[edit]

Prorenone can be synthesized via aJohnson–Corey–Chaykovsky reaction by reaction ofcanrenone withtrimethylsulfoxonium iodide andsodium hydride.[5]

See also

[edit]

References

[edit]
  1. ^abcClaire 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. ^abKamata 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. 
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
MRTooltip Mineralocorticoid receptor
Agonists
Antagonists
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists

This article about apregnanes is astub. You can help Wikipedia byexpanding it.

Stub icon

Thisdrug article relating to thecardiovascular system is astub. You can help Wikipedia byexpanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Prorenone&oldid=1308594114"
Categories:
Hidden categories:
[8]ページ先頭
©2009-2025 Movatter.jp