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Mespirenone

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
Mespirenone
Clinical data
Routes of
administration
Oral
ATC code
  • None
Identifiers
  • S-[(4aR,4bS,6aS,7S,7aS,8aS,8bS,8cR,9R)-4a,6a-Dimethyl-2,5'-dioxo-2,4',4b,5,5',6,6a,7a,8,8a,8b,8c,9,10-tetradecahydro-3'H,4aH-spiro[cyclopropa[4,5]cyclopenta[1,2-a]phenanthrene-7,2'-furan]-9-yl]ethane thioate
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC25H30O4S
Molar mass426.57 g·mol−1
3D model (JSmol)
  • CC(=O)SC1CC2=CC(=O)C=CC2(C3C1C4C5CC5C6(C4(CC3)C)CCC(=O)O6)C
  • InChI=InChI=1S/C25H30O4S/c1-13(26)30-19-11-14-10-15(27)4-7-23(14,2)17-5-8-24(3)22(21(17)19)16-12-18(16)25(24)9-6-20(28)29-25/h4,7,10,16-19,21-22H,5-6,8-9,11-12H2,1-3H3/t16-,17+,18+,19-,21+,22+,23+,24+,25+/m1/s1
  • Key:CPHJTSJQUQZOLJ-ISIDMKFXSA-N

Mespirenone (INN; developmental codeZK-94679; also known asΔ1-15β,16β-methylenespironolactone) is asteroidalantimineralocorticoid of thespirolactone group related tospironolactone that was never marketed.[1][2] Animal research found that it was 3.3-fold more potent as an antimineralocorticoid relative to spironolactone.[3] In addition to its antimineralocorticoid properties, mespirenone is also aprogestogen,antigonadotropin, andantiandrogen.[2][4] It is 2- to 3-fold as potent as spironolactone as a progestogen and antigonadotropin but its antiandrogenic activity is markedly reduced and weak (though still of significance) in comparison.[4][5] Mespirenone is also apotent and specificenzyme inhibitor of18-hydroxylase and thus ofmineralocorticoidbiosynthesis.[6] The drug was under development bySchering (nowBayer Schering Pharma) and reachedphase IIclinical trials but was discontinued in 1989.[7]

See also

[edit]

References

[edit]
  1. ^Elks J (14 November 2014).The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 775–.ISBN 978-1-4757-2085-3.
  2. ^abLosert W, Bittler D, Buse M, Casals-Stenzel J, Haberey M, Laurent H, et al. (November 1986). "Mespirenone and other 15,16-methylene-17-spirolactones, a new type of steroidal aldosterone antagonists".Arzneimittel-Forschung.36 (11):1583–1600.PMID 3028435.
  3. ^Weindel K, Lewicka S, Vecsei P (October 1991)."Interference of C17-spirosteroids with late steps of aldosterone biosynthesis. Structure-activity studies".Arzneimittel-Forschung.41 (10): 1082–1091 (1083).PMID 1799390.
  4. ^abNishino Y, Schröder H, el Etreby MF (December 1988). "Experimental studies on the endocrine side effects of new aldosterone antagonists".Arzneimittel-Forschung.38 (12):1800–1805.PMID 3245852.
  5. ^Opoku J, Kalimi M, Agarwal M, Qureshi D (February 1991). "Effect of a new mineralocorticoid antagonist mespirenone on aldosterone-induced hypertension".The American Journal of Physiology.260 (2 Pt 1):E269 –E271.doi:10.1152/ajpendo.1991.260.2.E269.PMID 1996630.
  6. ^Weindel K, Lewicka S, Vecsei P (September 1991). "Inhibitory effects of the novel anti-aldosterone compound mespirenone on adrenocortical steroidogenesis in vitro".Arzneimittel-Forschung.41 (9):946–949.PMID 1796922.
  7. ^Kolkhof P, Bärfacker L, Hillisch A, Haning H, Schäfer S (8 September 2008)."Nuclear receptors as targets in cardiovascular diseases". In Ottow E, Weinmann H (eds.).Nuclear Receptors as Drug Targets. John Wiley & Sons. pp. 410–.ISBN 978-3-527-62330-3.
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
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