Asoprisnil ecamate

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
PubChem CID
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) (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. ^ a b "Asoprisnil - AdisInsight".
  2. ^ a b 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. ^ a b 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.

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