Estetrol

  • CAT Number: R010032
  • CAS Number: 15183-37-6
  • Molecular Formula: C18H24O4
  • Molecular Weight: 304.38
  • Purity: 98%
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Estetrol (Cat No.:R010032) is a naturally occurring estrogen produced by the fetal liver during pregnancy, and it is now being developed for therapeutic use in contraception and hormone replacement therapy (HRT). Unlike other estrogens, estetrol exhibits selective tissue activity, providing beneficial effects on reproductive tissues while minimizing impact on the liver and breast, reducing the risk of clotting and breast cancer. Its unique profile makes it an ideal candidate for safe, effective hormonal treatments. Estetrol is used in combination oral contraceptives, offering enhanced safety and fewer side effects compared to traditional estrogens.


Catalog Number R010032
CAS Number 15183-37-6
Synonyms

(15α,16α,17β)-Estra-1,3,5(10)-triene-3,15,16,17-tetrol; ?Estra-1,3,5(10)-triene-3,15α,16α,17β-tetrol; 15α-Hydroxyestriol; 3,15α,16α,17β-Tetrahydroxyestra-1,3,5(10)-triene;

Molecular Formula C18H24O4
Purity 98%
Target Estrogen/progestogen Receptor
Target Protein

P03372,,,

Appearance Solid
Storage Dry, dark and at 2 - 8 °C for six months or -20°C for two years.
IC50 Estetrol has IC50 and Ki values of 17 nM and 4.9 nM against ER-α receptors
IUPAC Name (8R,9S,13S,14S,15R,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,15,16,17-tetrol
InChI InChI=1S/C18H24O4/c1-18-7-6-12-11-5-3-10(19)8-9(11)2-4-13(12)14(18)15(20)16(21)17(18)22/h3,5,8,12-17,19-22H,2,4,6-7H2,1H3/t12-,13-,14-,15-,16-,17+,18+/m1/s1
InChIKey AJIPIJNNOJSSQC-NYLIRDPKSA-N
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1[C@H]([C@H]([C@@H]2O)O)O)CCC4=C3C=CC(=C4)O
Reference

</br>1:Whole blood microsampling for the quantitation of estetrol without derivatization by liquid chromatography-tandem mass spectrometry. Nys G, Gallez A, Kok MGM, Cobraiville G, Servais AC, Piel G, Pequeux C, Fillet M.J Pharm Biomed Anal. 2017 Jun 5;140:258-265. doi: 10.1016/j.jpba.2017.02.060. Epub 2017 Mar 27. PMID: 28371720 </br>2:Regulatory effects of estetrol on the endothelial plasminogen pathway and endothelial cell migration. Montt-Guevara MM, Palla G, Spina S, Bernacchi G, Cecchi E, Campelo AE, Shortrede JE, Canu A, Simoncini T.Maturitas. 2017 May;99:1-9. doi: 10.1016/j.maturitas.2017.02.005. Epub 2017 Feb 12. PMID: 28364860 </br>3:Pharmacokinetics of the fetal estrogen estetrol in a multiple-rising-dose study in postmenopausal women. Coelingh Bennink HJT, Verhoeven C, Zimmerman Y, Visser M, Foidart JM, Gemzell-Danielsson K.Climacteric. 2017 Jun;20(3):285-289. doi: 10.1080/13697137.2017.1291608. Epub 2017 Mar 7. PMID: 28267365 </br>4:Pharmacodynamic effects of the fetal estrogen estetrol in postmenopausal women: results from a multiple-rising-dose study. Coelingh Bennink HJ, Verhoeven C, Zimmerman Y, Visser M, Foidart JM, Gemzell-Danielsson K.Menopause. 2017 Feb 6. doi: 10.1097/GME.0000000000000823. [Epub ahead of print] PMID: 28169916 </br>5:Estrogen receptors and estetrol-dependent neuroprotective actions: a pilot study. Tskitishvili E, Pequeux C, Munaut C, Viellevoye R, Nisolle M, Noël A, Foidart JM.J Endocrinol. 2017 Jan;232(1):85-95. Epub 2016 Oct 31. PMID: 27799463 Free PMC Article</br>6:Reduced hemostatic effects with drospirenone-based oral contraceptives containing estetrol vs. ethinyl estradiol. Kluft C, Zimmerman Y, Mawet M, Klipping C, Duijkers IJ, Neuteboom J, Foidart JM, Bennink HC.Contraception. 2017 Feb;95(2):140-147. doi: 10.1016/j.contraception.2016.08.018. Epub 2016 Sep 1. PMID: 27593335 </br>7:Clinical effects of the fetal estrogen estetrol in a multiple-rising-dose study in postmenopausal women. Coelingh Bennink HJ, Verhoeven C, Zimmerman Y, Visser M, Foidart JM, Gemzell-Danielsson K.Maturitas. 2016 Sep;91:93-100. doi: 10.1016/j.maturitas.2016.06.017. Epub 2016 Jun 23. PMID: 27451327 Free Article</br>8:Use of estetrol with other steroids for attenuation of neonatal hypoxic-ischemic brain injury: to combine or not to combine? Tskitishvili E, Pequeux C, Munaut C, Viellevoye R, Nisolle M, Noël A, Foidart JM.Oncotarget. 2016 Jun 7;7(23):33722-43. doi: 10.18632/oncotarget.9591. PMID: 27231853 Free PMC Article</br>9:Bleeding pattern and cycle control with estetrol-containing combined oral contraceptives: results from a phase II, randomised, dose-finding study (FIESTA). Apter D, Zimmerman Y, Beekman L, Mawet M, Maillard C, Foidart JM, Coelingh Bennink HJ.Contraception. 2016 Oct;94(4):366-73. doi: 10.1016/j.contraception.2016.04.015. Epub 2016 May 3. PMID: 27153745 Free Article</br>10:Inhibition of ovulation by administration of estetrol in combination with drospirenone or levonorgestrel: Results of a phase II dose-finding pilot study. Duijkers IJ, Klipping C, Zimmerman Y, Appels N, Jost M, Maillard C, Mawet M, Foidart JM, Coelingh Bennink HJ.Eur J Contracept Reprod Health Care. 2015;20(6):476-89. doi: 10.3109/13625187.2015.1074675. PMID: 26394847 Free PMC Article

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