Estetrol is is a potent, orally bioavailable, natural human fetal selective estrogen receptor modulator, since it acts in the rat as an estrogen on all tissues investigated except breast tumor tissue, where it has estrogen antagonistic properties in the presence of estradiol. Estetrol attenuates neonatal hypoxic-ischemic brain injury. Estetrol may be suitable as a potential drug for human use in applications such as hormone replacement therapy (vaginal atrophy, hot flushes), contraception and osteoporosis. Additional areas worth exploring are the treatment of breast and prostate cancer, hypoactive sexual desire disorder and topical use.
| 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 | 95% |
| Storage | -20°C |
| 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 | CC12CCC3C(C1C(C(C2O)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 |
