Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H24O4 |
| Molecular Weight | 304.3814 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@]12CC[C@]3([H])c4ccc(cc4CC[C@@]3([H])[C@]2([H])[C@]([H])([C@]([H])([C@]1([H])O)O)O)O
InChI
InChIKey=AJIPIJNNOJSSQC-NYLIRDPKSA-N
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
Estetrol is the natural human fetal selective estrogen receptor modulator. It is synthesized exclusively by the human fetal liver during pregnancy. Estetrol has a moderate affinity for human estrogen A receptor (ERa) and estrogen B receptor (ERb). 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. The most common drug-related adverse events were lower abdominal pain, nausea, headache, dysmenorrhoea, breast enlargement and acne. Estetrol had been in clinical trials for the treatment of breast and prostate cancers.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Simple chamber for temperature-controlled planar chromatography. | 2002 Sep 20 |
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| Endogenous estradiol metabolites stimulate the in vitro proliferation of human osteoblastic cells. | 2003 Apr |
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| [Estrogen: estrone (E1), estradiol (E2), estriol (E3) and estetrol (E4)]. | 2005 Aug |
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| Determination of steroids in human plasma using temperature-dependent inclusion chromatography for metabolomic investigations. | 2006 Feb 3 |
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| Characterization of human fetal cord blood steroid profiles in relation to fetal sex and mode of delivery using temperature-dependent inclusion chromatography and principal component analysis (PCA). | 2007 Aug 15 |
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| Maternal and fetal estetrol levels during pregnancy. | 2008 |
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| In vitro effects of estetrol on receptor binding, drug targets and human liver cell metabolism. | 2008 |
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| A new route of synthesis of estetrol. | 2008 |
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| Estetrol review: profile and potential clinical applications. | 2008 |
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| Estetrol does not bind sex hormone binding globulin or increase its production by human HepG2 cells. | 2008 |
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| First human exposure to exogenous single-dose oral estetrol in early postmenopausal women. | 2008 |
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| Estrogenic uterovaginal effects of oral estetrol in the modified Allen-Doisy test. | 2008 |
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| Preventive effect of oral estetrol in a menopausal hot flush model. | 2008 |
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| Oral bioavailability and bone-sparing effects of estetrol in an osteoporosis model. | 2008 |
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| Estetrol: a unique steroid in human pregnancy. | 2008 |
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| Interaction of native alpha-cyclodextrin, beta-cyclodextrin and gamma-cyclodextrin and their hydroxypropyl derivatives with selected organic low molecular mass compounds at elevated and subambient temperature under RP-HPLC conditions. | 2008 Aug |
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| Ovulation inhibition by estetrol in an in vivo model. | 2008 Mar |
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| Estetrol: a unique steroid in human pregnancy. | 2008 May |
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| Clinical applications for estetrol. | 2009 Mar |
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| Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: I. Optimization of separation protocol. | 2009 Oct 30 |
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| Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: II. Fast screening of free steroids and related low-molecular-mass compounds fraction in the environmental samples derived from surface waters, treated and untreated sewage waters as well as activated sludge material. | 2009 Oct 30 |
|
| [Estrogen: estrone (E1), estradiol (E2), estriol (E3) and estetrol (E4)]. | 2010 Jul |
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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FDA ORPHAN DRUG |
678119
Created by
admin on Sat Jun 26 07:40:53 UTC 2021 , Edited by admin on Sat Jun 26 07:40:53 UTC 2021
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EU-Orphan Drug |
EU/3/17/1865
Created by
admin on Sat Jun 26 07:40:53 UTC 2021 , Edited by admin on Sat Jun 26 07:40:53 UTC 2021
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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ESTETROL
Created by
admin on Sat Jun 26 07:40:53 UTC 2021 , Edited by admin on Sat Jun 26 07:40:53 UTC 2021
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10439
Created by
admin on Sat Jun 26 07:40:53 UTC 2021 , Edited by admin on Sat Jun 26 07:40:53 UTC 2021
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PRIMARY | |||
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15183-37-6
Created by
admin on Sat Jun 26 07:40:53 UTC 2021 , Edited by admin on Sat Jun 26 07:40:53 UTC 2021
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PRIMARY | |||
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C68928
Created by
admin on Sat Jun 26 07:40:53 UTC 2021 , Edited by admin on Sat Jun 26 07:40:53 UTC 2021
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PRIMARY | |||
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ENB39R14VF
Created by
admin on Sat Jun 26 07:40:53 UTC 2021 , Edited by admin on Sat Jun 26 07:40:53 UTC 2021
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PRIMARY | |||
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27125
Created by
admin on Sat Jun 26 07:40:53 UTC 2021 , Edited by admin on Sat Jun 26 07:40:53 UTC 2021
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PRIMARY | |||
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DB12235
Created by
admin on Sat Jun 26 07:40:53 UTC 2021 , Edited by admin on Sat Jun 26 07:40:53 UTC 2021
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15183-37-6
Created by
admin on Sat Jun 26 07:40:53 UTC 2021 , Edited by admin on Sat Jun 26 07:40:53 UTC 2021
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PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
