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Asoprisnil ecamate

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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
IUPAC name
  • phenanthren-11-yl]phenyl]methylideneamino] N-ethylcarbamate
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC31H40N2O5
Molar mass520.670 g·mol
3D model (JSmol)
SMILES
  • CCNC(=O)O/N=C/C1=CC=C(C=C1)2C3((CC3(COC)OC)4C2=C5CCC(=O)C=C5CC4)C
InChI
  • 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) (developmental code name J-956) is a synthetic, steroidal selective progesterone receptor modulator (SPRM) which was under development for the treatment of endometriosis, uterine fibroids, and menopausal symptoms but was discontinued. It is a potent and highly selective ligand of the progesterone receptor with mixed agonistic and antagonistic activity and much reduced antiglucocorticoid activity relative to mifepristone. The drug reached phase III clinical trials for the aforementioned indications prior to its discontinuation.

See also

References

  1. ^ "Asoprisnil - AdisInsight".
  2. ^ Schubert 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. ^ Chwalisz 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

Glucocorticoid receptor modulators
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Receptor/signaling modulators
Glucocorticoids and antiglucocorticoids
Mineralocorticoid receptor modulators
List of corticosteroids
Progesterone receptor modulators
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens
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