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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24O4
Molecular Weight 304.3808
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTETROL ANHYDROUS

SMILES

[H][C@@]12[C@@H](O)[C@@H](O)[C@H](O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C=C4

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
Molecular Formula C18H24O4
Molecular Weight 304.3808
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

2021
478
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
822
 4.9 nM [Ki]
Modulator
822
 19.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Phase III
663
Unknown

Approved Use

Unknown
Primary
Phase II
1144
Unknown

Approved Use

Unknown
Primary
Phase I
424
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
100 mg single, oral
Highest studied dose
Dose: 100 mg
Route: oral
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/18464021
Page: p.34
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/18464021
Page: p.34
Sources:
https://pubmed.ncbi.nlm.nih.gov/18464021
Page: p.34
15 mg 1 times / day multiple, oral
Minumum effective dose
Dose: 15 mg, 1 times / day
Route: oral
Route: multiple
Dose: 15 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32379217
Page: p.855
unhealthy, ADULT
n = 49
Health Status: unhealthy
Condition: reproductive system disease
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 49
Sources:
https://pubmed.ncbi.nlm.nih.gov/32379217
Page: p.855
Disc. AE: uterine bleedin...
AEs leading to
discontinuation/dose reduction:
uterine bleedin (grade 3, 2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/32379217
Page: p.855
60 mg 1 times / day multiple, oral
Studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/33242131
Page: p.1837
unhealthy, ADULT
n = 3
Health Status: unhealthy
Condition: breast cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 3
Sources:
https://pubmed.ncbi.nlm.nih.gov/33242131
Page: p.1837
Sources:
https://pubmed.ncbi.nlm.nih.gov/33242131
Page: p.1837
AEs

AEs

AESignificanceDosePopulation
uterine bleedin grade 3, 2%
Disc. AE
15 mg 1 times / day multiple, oral
Minumum effective dose
Dose: 15 mg, 1 times / day
Route: oral
Route: multiple
Dose: 15 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32379217
Page: p.855
unhealthy, ADULT
n = 49
Health Status: unhealthy
Condition: reproductive system disease
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 49
Sources:
https://pubmed.ncbi.nlm.nih.gov/32379217
Page: p.855
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P007XA8
https://www.1pchem.com/search?query=1P007XA8
Angene
AGN-PC-0WH1SZ
http://www.angenechemical.com/productshow/AGN-PC-0WH1SZ.html
Axon MedChem
1926
https://www.axonmedchem.com/product/1926
BOC Sciences
15183-37-6
http://www.bocsci.com/description.asp?cas=15183-37-6
Cayman Chemical
18232
http://www.caymanchem.com/app/template/Product.vm/catalog/18232
Chem Scene
CS-0008552
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0008552
MolPort
MolPort-042-665-780
https://www.molport.com/shop/molecule-link/MolPort-042-665-780
MolPort
MolPort-046-856-563
https://www.molport.com/shop/molecule-link/MolPort-046-856-563
Ryan Scientific
101-93964
https://ryansci.com/products?q=101-93964&list_q=&search_type=exact
Tetrahedron
TS75748
http://www.thsci.com/search.do?q=TS75748
Toronto Research Chemicals
E668450
https://www.trc-canada.com/product-detail/?CatNum=E668450
eMolecules
31225888
https://orderbb.emolecules.com/search/#?query=31225888
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
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
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
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
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

Patents

US20050277625
2
WO2004041839A2
2
WO2013034780A3
2

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
In Vitro Use Guide
Binding of Estetrol at the glucocorticoid, progesterone and testosterone receptors was only 11–15% at a concentration of 10 uM/l. Estetrol at a high concentration of 10 uM/l did not inhibit the major cytochrome P450 enzymes CYP1A2, CYP2C9, CYP2C19, CYP2D6 and CYP3A4.
Substance Class Chemical
Created
by admin
on Thu Jul 06 22:00:13 UTC 2023
Edited
by admin
on Thu Jul 06 22:00:13 UTC 2023
Record UNII
ENB39R14VF
Record Status Validated (UNII)
Record Version
  • Download
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
ESTETROL (E4)
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 Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
EU-Orphan Drug EU/3/17/1865
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
Code System Code Type Description
WIKIPEDIA
ESTETROL
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
INN
10439
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID50164888
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
RXCUI
2539031
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
USAN
FG-207
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
NCI_THESAURUS
C68928
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
FDA UNII
ENB39R14VF
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
DAILYMED
ENB39R14VF
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
WIKIPEDIA
Estetrol (medication)
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
PUBCHEM
27125
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
DRUG BANK
DB12235
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
CHEBI
142773
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
CAS
15183-37-6
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
SMS_ID
100000172329
Created by admin on Thu Jul 06 22:00:14 UTC 2023 , Edited by admin on Thu Jul 06 22:00:14 UTC 2023
PRIMARY
Related Record Type Details
ESTROGEN RECEPTOR BETA
TARGET -> AGONIST
Ki
Structure of ESTETROL MONOHYDRATE
SOLVATE->ANHYDROUS
Structure of ESTETROL MONOHYDRATE
SALT/SOLVATE -> PARENT
ESTROGEN RECEPTOR
TARGET -> AGONIST
Ki
Related Record Type Details
Structure of ESTETROL ANHYDROUS
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
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