HEXESTROL

US Previously Marketed

First approved in 1943

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H22O2
Molecular Weight	270.3661
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[C@@H]([C@@H](CC)C1=CC=C(O)C=C1)C2=CC=C(O)C=C2

InChI

InChIKey=PBBGSZCBWVPOOL-HDICACEKSA-N

InChI=1S/C18H22O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,17-20H,3-4H2,1-2H3/t17-,18+

HIDE SMILES / InChI

Molecular Formula	C18H22O2
Molecular Weight	270.3661
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13462184https://www.drugbank.ca/drugs/DB07931
Curator's Comment: description was created based on several sources, including https://www.drugs.com/international/hexestrol.html | https://www.ncbi.nlm.nih.gov/pubmed/27816005 | https://www.ncbi.nlm.nih.gov/pubmed/92377 | https://www.ncbi.nlm.nih.gov/pubmed/6099050 | https://www.ncbi.nlm.nih.gov/pubmed/27816005

Hexestrol (INN) (brand name Synoestrol, Estrifar, Estronal, numerous others), also known as hexoestrol, and dihydro-diethylstilbestrol, is a synthetic, non-steroidal estrogen of the stilbestrol group related to diethylstilbestrol that was used to treat estrogen deficiency but is now no longer employed medically. Hexestrol has also been available and used in ester form, including as hexestrol diacetate, hexestrol dicaprylate, hexestrol diphosphate, and hexestrol dipropionate.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Estrogen receptor alpha 127 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19286283	Agonist 2678
Estrogen receptor beta 110 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19286283	Agonist 2678

Conditions

Condition	Modality	Highest Phase	Product
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13462184	Primary	Not Provided 504	Unknown Approved Use Unknown
Prostatic hypertrophy 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/92377	Primary	Not Provided 504	Unknown Approved Use Unknown
Prostate cancer 178 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6099050	Primary	Not Provided 504	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
AAA Chemistry	AR-1F9907
ABI Chem	AC1L4VIK
ABI Chem	AC1Q6SHR
Alfa Chemistry	13425-53-1
BOC Sciences	13425-53-1
ChemTik	CTK4F4434
MuseChem	M062714
NovoSeek	193055
ZINC	ZINC000003650624	http://zinc15.docking.org/substances/ZINC000003650624

PubMed

Title	Date	PubMed
[Changes in glycogen content in prostatic epithelial cells in dogs after administration of hormone preparations (methyltestosterone, hexestrol and hexestrol diphosphate)].	1957 Mar-Apr	13464687
Validation of screening method for residues of diethylstilbestrol, dienestrol, hexestrol, and zeranol in bovine urine using immunoaffinity chromatography and gas chromatography/mass spectrometry.	2003 Jul-Aug	14509418
Drug-induced steatohepatitis.	2003 May	12879993
[Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals].	2004 Apr	15272608
A unifying mechanism in the initiation of cancer and other diseases by catechol quinones.	2004 Dec	15650250
On-line coupling of pressurized capillary electrochromatography with end-column amperometric detection for analysis of estrogens.	2005 Jun	15920782
Simultaneous determination of residual stilbenes and stilbene metabolites in animal tissue by liquid chromatography-tandem mass spectrometry.	2007 Jun 1	17452030
Determination of synthetic hormones in animal urine by high-performance liquid chromatography/mass spectrometry.	2007 Mar-Apr	17474533
Dipotassium 4,4'-(hexane-3,4-di-yl)bis-(benzene-sulfonate) dihydrate.	2008 Jul 16	21203019
Determination of estrogens in wastewater using three-phase hollow fiber-mediated liquid-phase microextraction followed by HPLC.	2008 Mar	18275104
Steatohepatitis-inducing drugs trigger cytokeratin cross-links in hepatocytes. Possible contribution to Mallory-Denk body formation.	2008 Sep	18603402
[Effects of Yi Fu Ning soft gelatin capsules on reproductive endocrine-immune function of ovariectomized rats].	2009 Jul	19873736
Synthesis and applications of diethylstilbestrol-based molecularly imprinted polymer-coated hollow fiber tube.	2010 Mar 17	20172093
Selective activation of zebrafish estrogen receptor subtypes by chemicals by using stable reporter gene assay developed in a zebrafish liver cell line.	2012 Feb	22045033
Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities.	2012 Nov 19	23013281
Robust array-based coregulator binding assay predicting ERα-agonist potency and generating binding profiles reflecting ligand structure.	2013 Mar 18	23383871

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Rectal

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:50:41 GMT 2023` Edited by `admin` on `Sat Dec 16 16:50:41 GMT 2023`
Record UNII	10BI795R7D
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

HEXESTROL

Official Name

English

NSC-9894

Code

English

MESO-HEXESTROL

Common Name

English

PHENOL, 4,4'-((1R,2S)-1,2-DIETHYL-1,2-ETHANEDIYL)BIS-, REL-

Common Name

English

HEXESTROL [JAN]

Common Name

English

4,4'-(1,2-DIETHYLETHYLENE)DIPHENOL

Systematic Name

English

ERYTHROHEXESTROL

Common Name

English

hexestrol [INN]

Common Name

English

MESO-3,4-DI(P-HYDROXYPHENYL)-N-HEXANE

Common Name

English

Hexestrol [WHO-DD]

Common Name

English

HEXESTROL [MART.]

Common Name

English

PHENOL, 4,4'-(1,2-DIETHYL-1,2-ETHANEDIYL)BIS-, (R*,S*)-

Common Name

English

HEXESTROL [MI]

Common Name

English

MESOHEXESTROL

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2182