ESTETROL MONOHYDRATE

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 Search

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	C18H24O4
Molecular Weight	304.3808
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

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 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18464023	Modulator 828		4.9 nM [Ki]
Estrogen receptor beta 110 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18464023	Modulator 828		19.0 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Pregnancy 65 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27153745 https://www.ncbi.nlm.nih.gov/pubmed/26394847	Preventing	Phase III 656	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24997853	Primary	Phase II 1132	Unknown Approved Use Unknown
Prostate cancer 178 Sources: https://clinicaltrials.gov/ct2/show/NCT02718378	Primary	Phase I 428	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Simple chamber for temperature-controlled planar chromatography.	2002 Sep 20	12350114
Endogenous estradiol metabolites stimulate the in vitro proliferation of human osteoblastic cells.	2003 Apr	12708603
Maternal and fetal estetrol levels during pregnancy.	2008	18464026
A new route of synthesis of estetrol.	2008	18464024
Estetrol does not bind sex hormone binding globulin or increase its production by human HepG2 cells.	2008	18464022
Oral bioavailability and bone-sparing effects of estetrol in an osteoporosis model.	2008	18464016
Estetrol: a unique steroid in human pregnancy.	2008	18464015
Ovulation inhibition by estetrol in an in vivo model.	2008 Mar	18279689
Estetrol: a unique steroid in human pregnancy.	2008 May	18462934

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 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 Dec 16 15:09:42 GMT 2023` Edited by `admin` on `Sat Dec 16 15:09:42 GMT 2023`
Record UNII	KC3GI9UM9V
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ESTETROL MONOHYDRATE

Official Name

English

E4 monohydrate

Common 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