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Ulipristal

CAS No.:
159811-51-5
Catalog Number:
AG001REN
Molecular Formula:
C28H35NO3
Molecular Weight:
433.5824
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Product Description
Catalog Number:
AG001REN
Chemical Name:
Ulipristal
CAS Number:
159811-51-5
Molecular Formula:
C28H35NO3
Molecular Weight:
433.5824
MDL Number:
MFCD19443756
IUPAC Name:
(8S,11R,13S,14S,17R)-17-acetyl-11-[4-(dimethylamino)phenyl]-17-hydroxy-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
InChI:
InChI=1S/C28H35NO3/c1-17(30)28(32)14-13-25-23-11-7-19-15-21(31)10-12-22(19)26(23)24(16-27(25,28)2)18-5-8-20(9-6-18)29(3)4/h5-6,8-9,15,23-25,32H,7,10-14,16H2,1-4H3/t23-,24+,25-,27-,28-/m0/s1
InChI Key:
HKDLNTKNLJPAIY-WKWWZUSTSA-N
SMILES:
O=C1CCC2=C3[C@H](C[C@]4([C@H]([C@@H]3CCC2=C1)CC[C@]4(O)C(=O)C)C)c1ccc(cc1)N(C)C
UNII:
6J5J15Q2X8
Properties
Complexity:
877  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
433.262g/mol
Formal Charge:
0
Heavy Atom Count:
32  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
433.592g/mol
Monoisotopic Mass:
433.262g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
57.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.9  
Literature
Title Journal
Mechanism of Action of Ulipristal Acetate for Emergency Contraception: A Systematic Review. Frontiers in pharmacology 20150101
Ulipristal acetate - safety and pharmacokinetics following multiple doses of 10-50 mg per day. Journal of clinical pharmacy and therapeutics 20130801
Emergency contraception. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20130301
Ulipristal acetate as an emergency contraceptive agent. Expert opinion on pharmacotherapy 20120901
Pharmacokinetic evaluation of ulipristal acetate for uterine leiomyoma treatment. Expert opinion on drug metabolism & toxicology 20120701
Growth inhibition induced by antiprogestins RU-38486, ORG-31710, and CDB-2914 in ovarian cancer cells involves inhibition of cyclin dependent kinase 2. Investigational new drugs 20120601
Glucocorticoid receptor mediates the effect of progesterone on uterine natural killer cells. American journal of reproductive immunology (New York, N.Y. : 1989) 20120601
Glucocorticoid receptor activity discriminates between progesterone and medroxyprogesterone acetate effects in breast cells. Breast cancer research and treatment 20120101
Updates in hormonal emergency contraception. Pharmacotherapy 20110901
Efficacy and tolerability of CDB-2914 treatment for symptomatic uterine fibroids: a randomized, double-blind, placebo-controlled, phase IIb study. Fertility and sterility 20110201
Update on emergency contraception. Advances in therapy 20110201
Defining reality: the potential role of pharmacists in assessing the impact of progesterone receptor modulators and misoprostol in reproductive health. The Annals of pharmacotherapy 20110101
[Update on current care guidelines: emergency contraception]. Duodecim; laaketieteellinen aikakauskirja 20110101
Indian Hedgehog and its targets in human endometrium: menstrual cycle expression and response to CDB-2914. The Journal of clinical endocrinology and metabolism 20101201
Ulisprisal acetate: a novel molecule and 5-day emergency contraceptive. Obstetrics and gynecology 20101201
Is it worth paying more for emergency hormonal contraception? The cost-effectiveness of ulipristal acetate versus levonorgestrel 1.5 mg. The journal of family planning and reproductive health care 20101001
Immediate pre-ovulatory administration of 30 mg ulipristal acetate significantly delays follicular rupture. Human reproduction (Oxford, England) 20100901
Ulipristal acetate for emergency contraception. Drugs of today (Barcelona, Spain : 1998) 20100901
Ulipristal - a new emergency contraceptive pill. Drug and therapeutics bulletin 20100801
Progesterone receptor modulators. The journal of family planning and reproductive health care 20100701
Ulipristal acetate for emergency contraception? Lancet (London, England) 20100508
Ulipristal acetate for emergency contraception? Lancet (London, England) 20100508
Translational research in women's health: from bedside to bench and from bench to bedside. International journal of gynaecology and obstetrics: the official organ of the International Federation of Gynaecology and Obstetrics 20100501
Cell-type specific actions of progesterone receptor modulators in the regulation of uterine leiomyoma growth. Seminars in reproductive medicine 20100501
Endometrial effects of a single early luteal dose of the selective progesterone receptor modulator CDB-2914. Fertility and sterility 20100401
Intrauterine administration of CDB-2914 (Ulipristal) suppresses the endometrium of rhesus macaques. Contraception 20100401
LNG may still be the best oral EC option. The journal of family planning and reproductive health care 20100401
Ulipristal. Postcoital contraception: no better than levonorgestrel. Prescrire international 20100401
Emergency contraception: update and review. Seminars in reproductive medicine 20100301
Ulipristal acetate versus levonorgestrel for emergency contraception: a randomised non-inferiority trial and meta-analysis. Lancet (London, England) 20100213
Towards more effective emergency contraception? Lancet (London, England) 20100213
Randomized placebo-controlled trial of CDB-2914 in new users of a levonorgestrel-releasing intrauterine system shows only short-lived amelioration of unscheduled bleeding. Human reproduction (Oxford, England) 20100201
Ulipristal acetate taken 48-120 hours after intercourse for emergency contraception. Obstetrics and gynecology 20100201
The need to take a 'new look' at emergency contraception. The journal of family planning and reproductive health care 20100101
Clinical utility of progesterone receptor modulators and their effect on the endometrium. Current opinion in obstetrics & gynecology 20090801
Persistence of an intact endometrial matrix and vessels structure in women exposed to VA-2914, a selective progesterone receptor modulator. The Journal of clinical endocrinology and metabolism 20081101
CDB-2914 for uterine leiomyomata treatment: a randomized controlled trial. Obstetrics and gynecology 20080501
Progesterone receptor modulator CDB-2914 induces extracellular matrix metalloproteinase inducer in cultured human uterine leiomyoma cells. Molecular human reproduction 20080301
The activities of progesterone receptor isoform A and B are differentially modulated by their ligands in a gene-selective manner. International journal of cancer 20080101
Action of progesterone receptor modulators on uterine leiomyomas. Clinical and experimental obstetrics & gynecology 20080101
Ulipristal, a progesterone receptor antagonist as a contraceptive and for the treatment of uterine fibroids. Current opinion in investigational drugs (London, England : 2000) 20071001
Effects of the progesterone receptor modulator VA2914 in a continuous low dose on the hypothalamic-pituitary-ovarian axis and endometrium in normal women: a prospective, randomized, placebo-controlled trial. The Journal of clinical endocrinology and metabolism 20070901
Effects of levonorgestrel-releasing IUS and progesterone receptor modulator PRM CDB-2914 on uterine leiomyomas. Contraception 20070601
Progesterone and progesterone receptor modulator in uterine leiomyoma growth. Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology 20070401
A novel pathway involving progesterone receptor, endothelin-2, and endothelin receptor B controls ovulation in mice. Molecular endocrinology (Baltimore, Md.) 20061101
Emergency contraception: politics and science move forward. Obstetrics and gynecology 20061101
Progesterone receptor modulator for emergency contraception: a randomized controlled trial. Obstetrics and gynecology 20061101
Progesterone receptor modulator CDB-2914 down-regulates vascular endothelial growth factor, adrenomedullin and their receptors and modulates progesterone receptor content in cultured human uterine leiomyoma cells. Human reproduction (Oxford, England) 20060901
Inhibition of proliferation of endometrial stromal cells by trichostatin A, RU486, CDB-2914, N-acetylcysteine, and ICI 182780. Gynecologic and obstetric investigation 20060101
Progesterone receptor modulator CDB-2914 down-regulates proliferative cell nuclear antigen and Bcl-2 protein expression and up-regulates caspase-3 and poly(adenosine 5'-diphosphate-ribose) polymerase expression in cultured human uterine leiomyoma cells. The Journal of clinical endocrinology and metabolism 20050201
Selective progesterone receptor modulators and progesterone antagonists: mechanisms of action and clinical applications. Human reproduction update 20050101
In vitro antiprogestational/antiglucocorticoid activity and progestin and glucocorticoid receptor binding of the putative metabolites and synthetic derivatives of CDB-2914, CDB-4124, and mifepristone. The Journal of steroid biochemistry and molecular biology 20040301
Pharmacologic properties of CDB(VA)-2914. Steroids 20031101
Development of the selective progesterone receptor modulator CDB-2914 for clinical indications. Steroids 20031101
Luteal phase dose-response relationships of the antiprogestin CDB-2914 in normally cycling women. Human reproduction (Oxford, England) 20030901
CDB-4124 and its putative monodemethylated metabolite, CDB-4453, are potent antiprogestins with reduced antiglucocorticoid activity: in vitro comparison to mifepristone and CDB-2914. Molecular and cellular endocrinology 20020225
Properties