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MedKoo Cat#: 326904 | Name: Asoprisnil
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Asoprisnil
Asoprisnil
CAS#199396-76-4

Theoretical Analysis

MedKoo Cat#: 326904

Name: Asoprisnil

CAS#: 199396-76-4

Chemical Formula: C28H35NO4

Exact Mass: 449.2566

Molecular Weight: 449.59

Elemental Analysis: C, 74.80; H, 7.85; N, 3.12; O, 14.23

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
25mg USD 1,050.00 2 Weeks
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Related CAS #
No Data
Synonym
J867; J-867; J 867; Asoprisnil; Asoprisnilum.
IUPAC/Chemical Name
11beta-(4-((E)-(Hydroxyimino)methyl)phenyl)-17beta-methoxy-17-(methoxymethyl)estra-4,9-dien-3-one
InChi Key
GJMNAFGEUJBOCE-MEQIQULJSA-N
InChi Code
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
SMILES Code
C[C@@]12[C@@](COC)(OC)CC[C@@]1([H])[C@]3([H])CCC4=CC(CCC4=C3[C@@H](C5=CC=C(/C=N/O)C=C5)C2)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 449.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: 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. doi: 10.1016/j.steroids.2003.09.008. PMID: 14667995. 2: Islam MS, Afrin S, Jones SI, Segars J. Selective Progesterone Receptor Modulators-Mechanisms and Therapeutic Utility. Endocr Rev. 2020 Oct 1;41(5):bnaa012. doi: 10.1210/endrev/bnaa012. PMID: 32365199; PMCID: PMC8659360. 3: 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. doi: 10.1055/s-2004-828617. PMID: 15164306. 4: Lethaby A, Puscasiu L, Vollenhoven B. Preoperative medical therapy before surgery for uterine fibroids. Cochrane Database Syst Rev. 2017 Nov 15;11(11):CD000547. doi: 10.1002/14651858.CD000547.pub2. PMID: 29139105; PMCID: PMC6486044. 5: Goenka S, R Simon S. Asoprisnil, a Selective Progesterone Receptor Modulator (SPRM), Inhibits Melanosome Export in B16F10 Cells and HEMn-DP Melanocytes. Molecules. 2020 Aug 6;25(16):3581. doi: 10.3390/molecules25163581. PMID: 32781695; PMCID: PMC7465349. 6: 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. doi: 10.1055/s-2005-864034. PMID: 15714390. 7: Fu J, Song H, Zhou M, Zhu H, Wang Y, Chen H, Huang W. Progesterone receptor modulators for endometriosis. Cochrane Database Syst Rev. 2017 Jul 25;7(7):CD009881. doi: 10.1002/14651858.CD009881.pub2. PMID: 28742263; PMCID: PMC6483151. 8: Islam MS, Ciavattini A, Petraglia F, Castellucci M, Ciarmela P. Extracellular matrix in uterine leiomyoma pathogenesis: a potential target for future therapeutics. Hum Reprod Update. 2018 Jan 1;24(1):59-85. doi: 10.1093/humupd/dmx032. PMID: 29186429. 9: 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):277-283. doi: 10.1007/s11596-013-1111-1. Epub 2013 Apr 17. PMID: 23592144. 10: 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. PMID: 19176543. 11: 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. doi: 10.1152/ajpendo.00210.2007. Epub 2007 Jul 24. PMID: 17652152. 12: 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. doi: 10.1210/me.2006-0524. Epub 2007 Mar 13. PMID: 17356170. 13: 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. doi: 10.1016/j.fertnstert.2006.11.094. Epub 2007 Feb 20. PMID: 17307170. 14: Stewart EA, Diamond MP, Williams ARW, Carr BR, Myers ER, Feldman RA, Elger W, Mattia-Goldberg C, Schwefel BM, Chwalisz K. Safety and efficacy of the selective progesterone receptor modulator asoprisnil for heavy menstrual bleeding with uterine fibroids: pooled analysis of two 12-month, placebo- controlled, randomized trials. Hum Reprod. 2019 Apr 1;34(4):623-634. doi: 10.1093/humrep/dez007. PMID: 30865281; PMCID: PMC7967793. 15: 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. doi: 10.1210/jc.2006-0898. Epub 2006 Nov 14. PMID: 17105846. 16: 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. PMID: 18765509. 17: 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. doi: 10.1210/jc.2005-2379. Epub 2006 Feb 7. PMID: 16464945. 18: Diamond MP, Stewart EA, Williams ARW, Carr BR, Myers ER, Feldman RA, Elger W, Mattia-Goldberg C, Schwefel BM, Chwalisz K. A 12-month extension study to evaluate the safety and efficacy of asoprisnil in women with heavy menstrual bleeding and uterine fibroids. Hum Reprod Open. 2019 Nov 4;2019(4):hoz027. doi: 10.1093/hropen/hoz027. PMID: 31777761; PMCID: PMC6870550. 19: 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. doi: 10.1093/humrep/deh738. Epub 2005 Jan 21. PMID: 15665012. 20: Csatlós E, Rigó J Jr, Szabó I, Nagy Z, Joó JG. A méh leiomyomája [Uterine leiomyoma]. Orv Hetil. 2010 Oct 17;151(42):1734-41. Hungarian. doi: 10.1556/OH.2010.28977. PMID: 20889441.

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