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Asoprisnil ecamate

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Asoprisnil ecamate
Clinical data
Other namesJ-956; 11β-(4-((E)-(Ethylcarbamoyl-oxyimino)methyl)phenyl)-17β-methoxy-17α-(methoxymethyl)estra-4,9-dien-3-one
Identifiers
  • [(E)-[4-[(8S,11R,13S,14S,17S)-17-Methoxy-17-(methoxymethyl)-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-11-yl]phenyl]methylideneamino]N-ethylcarbamate
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC31H40N2O5
Molar mass520.670 g·mol−1
3D model (JSmol)
  • CCNC(=O)O/N=C/C1=CC=C(C=C1)[C@H]2C[C@]3([C@@H](CC[C@]3(COC)OC)[C@H]4C2=C5CCC(=O)C=C5CC4)C
  • InChI=1S/C31H40N2O5/c1-5-32-29(35)38-33-18-20-6-8-21(9-7-20)26-17-30(2)27(14-15-31(30,37-4)19-36-3)25-12-10-22-16-23(34)11-13-24(22)28(25)26/h6-9,16,18,25-27H,5,10-15,17,19H2,1-4H3,(H,32,35)/b33-18+/t25-,26+,27-,30-,31+/m0/s1
  • Key:XMCOWVOJIVSMEO-RCCUTSCYSA-N

Asoprisnil ecamate (INN; development codeJ-956) is asynthetic,steroidalselective progesterone receptor modulator (SPRM) which was under development for the treatment ofendometriosis,uterine fibroids, andmenopausalsymptoms but was discontinued.[1][2][3] It is apotent and highlyselectiveligand of theprogesterone receptor with mixedagonistic andantagonistic activity and much reducedantiglucocorticoid activity relative tomifepristone.[2][3][4] The drug reachedphase IIIclinical trials for the aforementioned indications prior to its discontinuation.[1]

See also

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References

[edit]
  1. ^ab"Asoprisnil - AdisInsight".
  2. ^abSchubert G, Elger W, Kaufmann G, Schneider B, Reddersen G, Chwalisz K (2005). "Discovery, chemistry, and reproductive pharmacology of asoprisnil and related 11beta-benzaldoxime substituted selective progesterone receptor modulators (SPRMs)".Seminars in Reproductive Medicine.23 (1):58–73.doi:10.1055/s-2005-864034.PMID 15714390.S2CID 260316786.
  3. ^abChwalisz K, Perez MC, Demanno D, Winkel C, Schubert G, Elger W (2005)."Selective progesterone receptor modulator development and use in the treatment of leiomyomata and endometriosis".Endocrine Reviews.26 (3):423–38.doi:10.1210/er.2005-0001.PMID 15857972.
  4. ^Chwalisz K, Garg R, Brenner R, Slayden O, Winkel C, Elger W (2006)."Role of nonhuman primate models in the discovery and clinical development of selective progesterone receptor modulators (SPRMs)".Reproductive Biology and Endocrinology.4 (Suppl 1) S8.doi:10.1186/1477-7827-4-S1-S8.PMC 1775068.PMID 17118172.

External links

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GRTooltip Glucocorticoid receptor
Agonists
Mixed
(SEGRMsTooltip Selective glucocorticoid receptor agonists)
Antagonists
Others
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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