ESTETROL ANHYDROUS

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18464023 | https://www.ncbi.nlm.nih.gov/pubmed/26394847 | https://www.ncbi.nlm.nih.gov/pubmed/24997853 | http://adisinsight.springer.com/drugs/800044874

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

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor alpha 123 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18464023	Modulator 777	Prostate cancer Breast cancer Pregnancy	4.90000000000000036 nM [Ki]
Estrogen receptor beta 106 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18464023	Modulator 777	Pregnancy Breast cancer Prostate cancer	19 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase
Pregnancy 64 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27153745 https://www.ncbi.nlm.nih.gov/pubmed/26394847	Preventing	Estrogen receptor alpha Estrogen receptor beta	Phase III 650
Breast cancer 411 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24997853	Primary	Estrogen receptor alpha Estrogen receptor beta	Phase II
Prostate cancer 161 Sources: https://clinicaltrials.gov/ct2/show/NCT02718378	Primary	Estrogen receptor alpha Estrogen receptor beta	Phase I 593

PubMed

Title	Date	PubMed
		252160577
[Estrogen: estrone (E1), estradiol (E2), estriol (E3) and estetrol (E4)].	2005 Aug	16149545
Determination of steroids in human plasma using temperature-dependent inclusion chromatography for metabolomic investigations.	2006 Feb 3	16364333
Maternal and fetal estetrol levels during pregnancy.	2008	18464026
In vitro effects of estetrol on receptor binding, drug targets and human liver cell metabolism.	2008	18464025
A new route of synthesis of estetrol.	2008	18464024
Estrogenic uterovaginal effects of oral estetrol in the modified Allen-Doisy test.	2008	18464018
Preventive effect of oral estetrol in a menopausal hot flush model.	2008	18464017
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	18563397
Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: I. Optimization of separation protocol.	2009 Oct 30	19362314
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	19356767

Patents

Sample Use Guides

In Vivo Use Guide

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

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

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Name

Type

Language

ESTETROL ANHYDROUS

Common Name

English

ESTETROL

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