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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24O4.H2O
Molecular Weight 322.3967
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTETROL MONOHYDRATE

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.O

InChI

InChIKey=XRJNAPXFAXBPAM-BVTDNVAGSA-N
InChI=1S/C18H24O4.H2O/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;1H2/t12-,13-,14-,15-,16-,17+,18+;/m1./s1

HIDE SMILES / InChI

Molecular Formula C18H24O4
Molecular Weight 304.3814
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
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
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
Substance Class Chemical
Created
by admin
on Fri Jun 25 23:58:30 UTC 2021
Edited
by admin
on Fri Jun 25 23:58:30 UTC 2021
Record UNII
KC3GI9UM9V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTETROL MONOHYDRATE
Official Name English
NEXTSTELLIS COMPONENT ESTETROL
Brand Name English
ESTETROL COMPONENT OF NEXTSTELLIS
Brand Name English
ESTETROL (HYDROUS) [USAN]
Common Name English
ESTRA-1,3,5(10)-TRIENE-3,15,16,17-TETROL, HYDRATE (1:1), (15.ALPHA.,16.ALPHA.,17.BETA.)-
Systematic Name English
ESTRA-1,3,5(10)-TRIENE-3,15.ALPHA.,16.ALPHA.,17.BETA.-TETROL MONOHYDRATE
Systematic Name English
Code System Code Type Description
PUBCHEM
135391051
Created by admin on Fri Jun 25 23:58:30 UTC 2021 , Edited by admin on Fri Jun 25 23:58:30 UTC 2021
PRIMARY
CAS
2055649-81-3
Created by admin on Fri Jun 25 23:58:30 UTC 2021 , Edited by admin on Fri Jun 25 23:58:30 UTC 2021
PRIMARY
FDA UNII
KC3GI9UM9V
Created by admin on Fri Jun 25 23:58:30 UTC 2021 , Edited by admin on Fri Jun 25 23:58:30 UTC 2021
PRIMARY
NCI_THESAURUS
C169963
Created by admin on Fri Jun 25 23:58:30 UTC 2021 , Edited by admin on Fri Jun 25 23:58:30 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY