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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
Structure of ESTETROL ANHYDROUS

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

HIDE SMILES / InChI
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Simple chamber for temperature-controlled planar chromatography.
2002 Sep 20
Endogenous estradiol metabolites stimulate the in vitro proliferation of human osteoblastic cells.
2003 Apr
[Estrogen: estrone (E1), estradiol (E2), estriol (E3) and estetrol (E4)].
2005 Aug
Determination of steroids in human plasma using temperature-dependent inclusion chromatography for metabolomic investigations.
2006 Feb 3
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
Maternal and fetal estetrol levels during pregnancy.
2008
In vitro effects of estetrol on receptor binding, drug targets and human liver cell metabolism.
2008
A new route of synthesis of estetrol.
2008
Estetrol review: profile and potential clinical applications.
2008
Estetrol does not bind sex hormone binding globulin or increase its production by human HepG2 cells.
2008
First human exposure to exogenous single-dose oral estetrol in early postmenopausal women.
2008
Estrogenic uterovaginal effects of oral estetrol in the modified Allen-Doisy test.
2008
Preventive effect of oral estetrol in a menopausal hot flush model.
2008
Oral bioavailability and bone-sparing effects of estetrol in an osteoporosis model.
2008
Estetrol: a unique steroid in human pregnancy.
2008
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
Ovulation inhibition by estetrol in an in vivo model.
2008 Mar
Estetrol: a unique steroid in human pregnancy.
2008 May
Clinical applications for estetrol.
2009 Mar
Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: I. Optimization of separation protocol.
2009 Oct 30
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
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: in combination with 3 mg drospirenone tablets
15 mg administered once daily for 13 consecutive cycles following a 24/4-day regimen.
Route of Administration: Oral
Binding of Estetrol at the glucocorticoid, progesterone and
Name Type Language
ESTETROL ANHYDROUS
Common Name English
ESTETROL
INN  
INN  
Preferred Name English
E4
Code English
ESTETROL [WHO-DD]
Common Name English
ESTRA-1,3,5(10)-TRIENE-3,15,16,17-TETROL, (15.ALPHA.,16.ALPHA.,17.BETA.)-
Systematic Name English
ESTETROL (ANHYDROUS) [USAN]
Common Name English
ESTRA-1,3,5(10)-TRIENE-3,15.ALPHA.,16.ALPHA.,17.BETA.-TETROL
Systematic Name English
ESTETROL [INN]
Common Name English
E-4
Code English
15.ALPHA.-HYDROXYESTRIOL
Common Name English
Classification Tree Code System Code
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
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
Code System Code Type Description
WIKIPEDIA
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
PRIMARY
INN
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
PRIMARY
EPA CompTox
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
PRIMARY
NCI_THESAURUS
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
PRIMARY
FDA UNII
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
PRIMARY
PUBCHEM
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
PRIMARY
DRUG BANK
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
PRIMARY
CAS
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
PRIMARY