Asoprisnil ecamate

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.[1][2][3] 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.[2][3][4] The drug reached phase III clinical trials for the aforementioned indications prior to its discontinuation.[1]

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
  • [(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
Chemical and physical data
FormulaC31H40N2O5
Molar mass520.670 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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

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.
  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.
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