(8S,11S,13S,14S,17S)-11-[4-[(E)-hydroxyiminomethyl]phenyl]-17-methoxy- 17-(methoxymethyl)-13-methyl-


CAS No. : 199396-76-4

(8S,11S,13S,14S,17S)-11-[4-[(E)-hydroxyiminomethyl]phenyl]-17-methoxy- 17-(methoxymethyl)-13-methyl-,199396-76-4
Product Details
Cat No:M139365
Molecular Formula:C28H35NO4
Molecular Weight:449.591
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Appearance:Solid powder
Purity: > 98%
Cat No:M139365
Cas No:199396-76-4
Product-Name:(8S,11S,13S,14S,17S)-11-[4-[(E)-hydroxyiminomethyl]phenyl]-17-methoxy- 17-(methoxymethyl)-13-methyl-
IUPAC Name:(8S,11R,13S,14S,17S)-11-[4-[(E)-hydroxyiminomethyl]phenyl]-17-methoxy-17-(methoxymethyl)-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
InChI:InChI=1S/C28H35NO4/c1-27-15-24(19-6-4-18(5-7-19)16-29-31)26-22-11-9-21(30)14-20(22)8-10-23(26)25(27)12-13-28(27,33-3)17-32-2/h4-7,14,16,23-25,31H,8-13,15,17H2,1-3H3/b29-16+/t23-,24+,25-,27-,28+/m0/s1
InChIKey:GJMNAFGEUJBOCE-MEQIQULJSA-N
SMILES:CC12CC(C3=C4CCC(=O)C=C4CCC3C1CCC2(COC)OC)C5=CC=C(C=C5)C=NO
Asoprisnil, also known as J867) is an investigational selective progesterone-receptor modulator developed by Schering and TAP Pharmaceutical Products, tested for treatment of progesterone-sensitive myomata. In 2005, phase-III trials were discontinued due to endometrial changes in patients. Whether asoprisnil will be marketed is uncertain.

1: Wilkens J, Male V, Ghazal P, Forster T, Gibson DA, Williams AR, Brito-Mutunayagam SL, Craigon M, Lourenco P, Cameron IT, Chwalisz K, Moffett A, Critchley HO. Uterine NK cells regulate endometrial bleeding in women and are suppressed by the progesterone receptor modulator asoprisnil. J Immunol. 2013 Sep 1;191(5):2226-35. doi: 10.4049/jimmunol.1300958. Epub 2013 Aug 2. PubMed PMID: 23913972; PubMed Central PMCID: PMC3843142.
2: Wu XL, Yu ZH, Qiu J, Yang YH, Shen XL, Su P. Postcoital administration of asoprisnil inhibited embryo implantation and disturbed ultrastructure of endometrium in implantation window in mice. J Huazhong Univ Sci Technolog Med Sci. 2013 Apr;33(2):277-83. doi: 10.1007/s11596-013-1111-1. Epub 2013 Apr 17. PubMed PMID: 23592144.
3: Maruo T, Ohara N, Yoshida S, Nakabayashi K, Sasaki H, Xu Q, Matsuo H, Sitruk-Ware R, Yamada H. Lessons learned from the preclinical drug discovery of asoprisnil and ulipristal for non-surgical treatment of uterine leiomyomas. Expert Opin Drug Discov. 2011 Sep;6(9):897-911. doi: 10.1517/17460441.2011.602670. Epub 2011 Jul 16. PubMed PMID: 22646213.
4: Wilkens J, Williams AR, Chwalisz K, Han C, Cameron IT, Critchley HO. Effect of asoprisnil on uterine proliferation markers and endometrial expression of the tumour suppressor gene, PTEN. Hum Reprod. 2009 May;24(5):1036-44. doi: 10.1093/humrep/den494. Epub 2009 Jan 27. PubMed PMID: 19176543.
5: Wilkens J, Chwalisz K, Han C, Walker J, Cameron IT, Ingamells S, Lawrence AC, Lumsden MA, Hapangama D, Williams AR, Critchley HO. Effects of the selective progesterone receptor modulator asoprisnil on uterine artery blood flow, ovarian activity, and clinical symptoms in patients with uterine leiomyomata scheduled for hysterectomy. J Clin Endocrinol Metab. 2008 Dec;93(12):4664-71. doi: 10.1210/jc.2008-1104. Epub 2008 Sep 2. PubMed PMID: 18765509.
6: Morikawa A, Ohara N, Xu Q, Nakabayashi K, DeManno DA, Chwalisz K, Yoshida S, Maruo T. Selective progesterone receptor modulator asoprisnil down-regulates collagen synthesis in cultured human uterine leiomyoma cells through up-regulating extracellular matrix metalloproteinase inducer. Hum Reprod. 2008 Apr;23(4):944-51. doi: 10.1093/humrep/den025. Epub 2008 Feb 15. PubMed PMID: 18281245.
7: Ohara N, Morikawa A, Chen W, Wang J, DeManno DA, Chwalisz K, Maruo T. Comparative effects of SPRM asoprisnil (J867) on proliferation, apoptosis, and the expression of growth factors in cultured uterine leiomyoma cells and normal myometrial cells. Reprod Sci. 2007 Dec;14(8 Suppl):20-7. doi: 10.1177/1933719107311464. PubMed PMID: 18089606.
8: Xu Q, Ohara N, Liu J, Nakabayashi K, DeManno D, Chwalisz K, Yoshida S, Maruo T. Selective progesterone receptor modulator asoprisnil induces endoplasmic reticulum stress in cultured human uterine leiomyoma cells. Am J Physiol Endocrinol Metab. 2007 Oct;293(4):E1002-11. Epub 2007 Jul 24. PubMed PMID: 17652152.
9: Madauss KP, Grygielko ET, Deng SJ, Sulpizio AC, Stanley TB, Wu C, Short SA, Thompson SK, Stewart EL, Laping NJ, Williams SP, Bray JD. A structural and in vitro characterization of asoprisnil: a selective progesterone receptor modulator. Mol Endocrinol. 2007 May;21(5):1066-81. Epub 2007 Mar 13. PubMed PMID: 17356170.
10: Williams AR, Critchley HO, Osei J, Ingamells S, Cameron IT, Han C, Chwalisz K. The effects of the selective progesterone receptor modulator asoprisnil on the morphology of uterine tissues after 3 months treatment in patients with symptomatic uterine leiomyomata. Hum Reprod. 2007 Jun;22(6):1696-704. Epub 2007 Mar 5. PubMed PMID: 17339234.
11: Chwalisz K, Larsen L, Mattia-Goldberg C, Edmonds A, Elger W, Winkel CA. A randomized, controlled trial of asoprisnil, a novel selective progesterone receptor modulator, in women with uterine leiomyomata. Fertil Steril. 2007 Jun;87(6):1399-412. Epub 2007 Feb 20. PubMed PMID: 17307170.
12: Sasaki H, Ohara N, Xu Q, Wang J, DeManno DA, Chwalisz K, Yoshida S, Maruo T. A novel selective progesterone receptor modulator asoprisnil activates tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-mediated signaling pathway in cultured human uterine leiomyoma cells in the absence of comparable effects on myometrial cells. J Clin Endocrinol Metab. 2007 Feb;92(2):616-23. Epub 2006 Nov 14. PubMed PMID: 17105846.
13: Wang J, Ohara N, Wang Z, Chen W, Morikawa A, Sasaki H, DeManno DA, Chwalisz K, Maruo T. A novel selective progesterone receptor modulator asoprisnil (J867) down-regulates the expression of EGF, IGF-I, TGFbeta3 and their receptors in cultured uterine leiomyoma cells. Hum Reprod. 2006 Jul;21(7):1869-77. Epub 2006 Apr 13. PubMed PMID: 16613890.
14: Chen W, Ohara N, Wang J, Xu Q, Liu J, Morikawa A, Sasaki H, Yoshida S, Demanno DA, Chwalisz K, Maruo T. A novel selective progesterone receptor modulator asoprisnil (J867) inhibits proliferation and induces apoptosis in cultured human uterine leiomyoma cells in the absence of comparable effects on myometrial cells. J Clin Endocrinol Metab. 2006 Apr;91(4):1296-304. Epub 2006 Feb 7. PubMed PMID: 16464945.
15: Molecule of the month: asoprisnil. Drug News Perspect. 2005 Jul-Aug;18(6):404. PubMed PMID: 16247518.
16: Schubert G, Elger W, Kaufmann G, Schneider B, Reddersen G, Chwalisz K. Discovery, chemistry, and reproductive pharmacology of asoprisnil and related 11beta-benzaldoxime substituted selective progesterone receptor modulators (SPRMs). Semin Reprod Med. 2005 Feb;23(1):58-73. Review. PubMed PMID: 15714390.
17: Chwalisz K, Elger W, Stickler T, Mattia-Goldberg C, Larsen L. The effects of 1-month administration of asoprisnil (J867), a selective progesterone receptor modulator, in healthy premenopausal women. Hum Reprod. 2005 Apr;20(4):1090-9. Epub 2005 Jan 21. PubMed PMID: 15665012.
18: Chwalisz K, DeManno D, Garg R, Larsen L, Mattia-Goldberg C, Stickler T. Therapeutic potential for the selective progesterone receptor modulator asoprisnil in the treatment of leiomyomata. Semin Reprod Med. 2004 May;22(2):113-9. Review. PubMed PMID: 15164306.
19: DeManno D, Elger W, Garg R, Lee R, Schneider B, Hess-Stumpp H, Schubert G, Chwalisz K. Asoprisnil (J867): a selective progesterone receptor modulator for gynecological therapy. Steroids. 2003 Nov;68(10-13):1019-32. Review. PubMed PMID: 14667995.

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