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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24O4.H2O
Molecular Weight 322.396
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTETROL MONOHYDRATE

SMILES

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

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

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
Simple chamber for temperature-controlled planar chromatography.
2002 Sep 20
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
First human exposure to exogenous single-dose oral estetrol in early postmenopausal women.
2008
[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 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 20:43:25 UTC 2023
Edited
by admin
on Thu Jul 06 20:43:25 UTC 2023
Record UNII
KC3GI9UM9V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTETROL MONOHYDRATE
Official Name English
Estetrol monohydrate [WHO-DD]
Common Name English
ESTETROL [ORANGE BOOK]
Common Name English
NEXTSTELLIS COMPONENT ESTETROL
Brand Name English
ESTETROL COMPONENT OF NEXTSTELLIS
Brand Name English
ESTETROL (HYDROUS) [USAN]
Common Name English
ESTETROL HYDRATE
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
ESTETROL HYDRATE [JAN]
Common Name English
Code System Code Type Description
SMS_ID
300000014640
Created by admin on Thu Jul 06 20:43:25 UTC 2023 , Edited by admin on Thu Jul 06 20:43:25 UTC 2023
PRIMARY
PUBCHEM
135391051
Created by admin on Thu Jul 06 20:43:25 UTC 2023 , Edited by admin on Thu Jul 06 20:43:25 UTC 2023
PRIMARY
CAS
2055649-81-3
Created by admin on Thu Jul 06 20:43:25 UTC 2023 , Edited by admin on Thu Jul 06 20:43:25 UTC 2023
PRIMARY
FDA UNII
KC3GI9UM9V
Created by admin on Thu Jul 06 20:43:25 UTC 2023 , Edited by admin on Thu Jul 06 20:43:25 UTC 2023
PRIMARY
RXCUI
2539035
Created by admin on Thu Jul 06 20:43:25 UTC 2023 , Edited by admin on Thu Jul 06 20:43:25 UTC 2023
PRIMARY
DAILYMED
KC3GI9UM9V
Created by admin on Thu Jul 06 20:43:25 UTC 2023 , Edited by admin on Thu Jul 06 20:43:25 UTC 2023
PRIMARY
NCI_THESAURUS
C169963
Created by admin on Thu Jul 06 20:43:25 UTC 2023 , Edited by admin on Thu Jul 06 20:43:25 UTC 2023
PRIMARY
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