Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H24O8P2 |
| Molecular Weight | 430.3259 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@@H]([C@@H](CC)C1=CC=C(OP(O)(O)=O)C=C1)C2=CC=C(OP(O)(O)=O)C=C2
InChI
InChIKey=JBDIWCWZUDNWTL-HDICACEKSA-N
InChI=1S/C18H24O8P2/c1-3-17(13-5-9-15(10-6-13)25-27(19,20)21)18(4-2)14-7-11-16(12-8-14)26-28(22,23)24/h5-12,17-18H,3-4H2,1-2H3,(H2,19,20,21)(H2,22,23,24)/t17-,18+
| Molecular Formula | C18H24O8P2 |
| Molecular Weight | 430.3259 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator'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
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Endocrine disruption screening by protein and gene expression of vitellogenin in freshly isolated and cryopreserved rainbow trout hepatocytes. | 2014-08-18 |
|
| Robust array-based coregulator binding assay predicting ERα-agonist potency and generating binding profiles reflecting ligand structure. | 2013-03-18 |
|
| Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities. | 2012-11-19 |
|
| Selective activation of zebrafish estrogen receptor subtypes by chemicals by using stable reporter gene assay developed in a zebrafish liver cell line. | 2012-02 |
|
| Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands. | 2010-12-05 |
|
| Optimization and prevalidation of the in vitro ERalpha CALUX method to test estrogenic and antiestrogenic activity of compounds. | 2010-08 |
|
| The assessment of estrogenic or anti-estrogenic activity of chemicals by the human stably transfected estrogen sensitive MELN cell line: results of test performance and transferability. | 2010-08 |
|
| Assessment of a robust model protocol with accelerated throughput for a human recombinant full length estrogen receptor-alpha binding assay: protocol optimization and intralaboratory assay performance as initial steps towards validation. | 2010-08 |
|
| Diethylstilbestrol and other nonsteroidal estrogens: novel class of store-operated calcium channel modulators. | 2010-05 |
|
| Synthesis and applications of diethylstilbestrol-based molecularly imprinted polymer-coated hollow fiber tube. | 2010-03-17 |
|
| Determination of anabolic steroids in bovine urine by liquid chromatography-tandem mass spectrometry. | 2009-08-01 |
|
| [Effects of Yi Fu Ning soft gelatin capsules on reproductive endocrine-immune function of ovariectomized rats]. | 2009-07 |
|
| Towards high-throughput identification of endocrine disrupting compounds with mass spectrometry. | 2009-06 |
|
| [Determination of hormone multi-residues in animal tissues by gas chromatography-mass spectrometry]. | 2009-05 |
|
| Development of a rapid method for the analysis of synthetic growth promoters in bovine muscle using liquid chromatography tandem mass spectrometry. | 2009-04-01 |
|
| Biochemical and structural characterization of a short-chain dehydrogenase/reductase of Thermus thermophilus HB8: a hyperthermostable aldose-1-dehydrogenase with broad substrate specificity. | 2009-03-16 |
|
| Characterization of a rat NADPH-dependent aldo-keto reductase (AKR1B13) induced by oxidative stress. | 2009-03-16 |
|
| Structure of the G225P/G226P mutant of mouse 3(17)alpha-hydroxysteroid dehydrogenase (AKR1C21) ternary complex: implications for the binding of inhibitor and substrate. | 2009-03 |
|
| Treatments for suppression of lactation. | 2009-01-21 |
|
| [Hexestrol inhibits ATP-induced contractile response of isolated preparations of pregnant human uterus]. | 2009-01-15 |
|
| In silico identification of anthropogenic chemicals as ligands of zebrafish sex hormone binding globulin. | 2009-01-01 |
|
| Potential use of an estrogen-glucocorticoid receptor chimera as a drug screen for tissue selective estrogenic activity. | 2009-01 |
|
| Six-month depot formulation of leuprorelin acetate in the treatment of prostate cancer. | 2009 |
|
| Steatohepatitis-inducing drugs trigger cytokeratin cross-links in hepatocytes. Possible contribution to Mallory-Denk body formation. | 2008-09 |
|
| Dipotassium 4,4'-(hexane-3,4-di-yl)bis-(benzene-sulfonate) dihydrate. | 2008-07-16 |
|
| Effects of hexestrol on mouse ovarian morphology and ovulation. | 2008-06-20 |
|
| Development and in-house validation of an LC-MS/MS method for the determination of stilbenes and resorcylic acid lactones in bovine urine. | 2008-06 |
|
| Synthesis of [4.6.4.6]fenestradienes and [4.6.4.6]fenestrenes based on an 8pi-6pi-cyclization-oxidation cascade. | 2008-04-16 |
|
| Determination of estrogens in wastewater using three-phase hollow fiber-mediated liquid-phase microextraction followed by HPLC. | 2008-03 |
|
| Studies on thermal reactivity of beta-(1,2-allenyl)butenolides and 2-allyl-3-allenylcyclohex-2-enones. | 2008 |
|
| Activity of xenoestrogens at nanomolar concentrations in the E-Screen assay. | 2007-12 |
|
| Comparison of time-resolved fluoroimmunoassay for determining hexoestrol residues in chicken muscle tissues based on polyclonal antibodies with liquid chromatography and tandem mass spectrometry. | 2007-09-08 |
|
| Interactions of diethylstilbestrol (DES) and DES analogs with membrane progestin receptor-alpha and the correlation with their nongenomic progestin activities. | 2007-07 |
|
| A new molecularly imprinted polymer for the on-column solid-phase extraction of diethylstilbestrol from aqueous samples. | 2007-07 |
|
| Simultaneous determination of residual stilbenes and stilbene metabolites in animal tissue by liquid chromatography-tandem mass spectrometry. | 2007-06-01 |
|
| Determination of synthetic hormones in animal urine by high-performance liquid chromatography/mass spectrometry. | 2007-05-04 |
|
| HPLC-tandem mass spectrometric method to characterize resveratrol metabolism in humans. | 2007-02 |
|
| The use of liquid membranes in the multi-residue extraction of stilbenes in a variety of biological matrices and their detection with LC-ES-MS. | 2007-01-16 |
|
| Catechol quinones of estrogens in the initiation of breast, prostate, and other human cancers: keynote lecture. | 2006-11 |
|
| [Determination of residues of three stilbene drugs in animal tissues using gas chromatography-mass spectrometry]. | 2006-09 |
|
| Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. | 1997-03 |
|
| Relationship of human liver dihydrodiol dehydrogenases to hepatic bile-acid-binding protein and an oxidoreductase of human colon cells. | 1996-01-15 |
|
| Subacute toxicity of diethylstilboestrol and hexoestrol in the female rat, and the effects of clomiphene pretreatment. | 1988-03 |
|
| Carcinogenicity and metabolic activation of hexestrol. | 1985-10 |
|
| Clear-cell adenocarcinoma of the genital tract in young females. Registry report. | 1972-12-21 |
|
| [Therapy of carcinoma of the prostate with hexestrol diphosphate administered by rectal route]. | 1960-07-01 |
|
| [Remote clinical results in patients with prostatic carcinoma treated with hexestrol diphosphate]. | 1959-11-01 |
|
| [Preliminary results obtained with hexestrol diphosphate in therapy of prostate cancer]. | 1957-12-07 |
|
| [Changes in glycogen content in prostatic epithelial cells in dogs after administration of hormone preparations (methyltestosterone, hexestrol and hexestrol diphosphate)]. | 1957-03-01 |
|
| [Experimental research on prostatic antineoplastic agent: hexestrol diphosphate]. | 1956-07-01 |
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
30L14W008X
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| Record Status |
Validated (UNII)
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| Record Version |
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m6007
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30L14W008X
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Hexestrol diphosphate
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193055
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DTXSID901016489
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14188-82-0
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24809-02-7
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SALT/SOLVATE -> PARENT |
