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Chemical compound
Asoprisnil ecamate
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Other names | J-956; 11β-(4-((E)-(Ethylcarbamoyl-oxyimino)methyl)phenyl)-17β-methoxy-17α-(methoxymethyl)estra-4,9-dien-3-one |
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[(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
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PubChem
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ChEMBL | |
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Formula | C31H40N2O5 |
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Molar mass | 520.670 g·mol−1 |
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3D model (
JSmol) | |
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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
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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
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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]
See also
References
- ^
a
b
"Asoprisnil - AdisInsight".
- ^
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.
- ^
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.
-
^ 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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SPRMsTooltip Selective progesterone receptor modulators) | |
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mPRTooltip Membrane progesterone receptor (
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