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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

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

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

Targets

Targets

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
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: Page: p.34
healthy, ADULT
n = 6
Health Status: healthy
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 6
Sources: 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: 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: Page: p.855
Disc. AE: uterine bleedin...
AEs leading to
discontinuation/dose reduction:
uterine bleedin (grade 3, 2%)
Sources: 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: 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: 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: 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: Page: p.855
PubMed

PubMed

TitleDatePubMed
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
Estetrol review: profile and potential clinical applications.
2008
Preventive effect of oral estetrol in a menopausal hot flush model.
2008
Estetrol: a unique steroid in human pregnancy.
2008
Ovulation inhibition by estetrol in an in vivo model.
2008 Mar
Estetrol: a unique steroid in human pregnancy.
2008 May
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 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 Sat Jun 26 07:40:53 UTC 2021
Edited
by admin
on Sat Jun 26 07:40:53 UTC 2021
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
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
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY