Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C34H50O4 |
| Molecular Weight | 522.7584 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCC(=O)OC1=CC=C(C=C1)[C@@H](CC)[C@@H](CC)C2=CC=C(OC(=O)CCCCCCC)C=C2
InChI
InChIKey=JZMCTYYCJNIOBO-MEKGRNQZSA-N
InChI=1S/C34H50O4/c1-5-9-11-13-15-17-33(35)37-29-23-19-27(20-24-29)31(7-3)32(8-4)28-21-25-30(26-22-28)38-34(36)18-16-14-12-10-6-2/h19-26,31-32H,5-18H2,1-4H3/t31-,32+
| Molecular Formula | C34H50O4 |
| Molecular Weight | 522.7584 |
| 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 |
|---|---|---|
| [Experimental research on prostatic antineoplastic agent: hexestrol diphosphate]. | 1956 Jul-Dec |
|
| [Preliminary results obtained with hexestrol diphosphate in therapy of prostate cancer]. | 1957 Dec 7 |
|
| [Changes in glycogen content in prostatic epithelial cells in dogs after administration of hormone preparations (methyltestosterone, hexestrol and hexestrol diphosphate)]. | 1957 Mar-Apr |
|
| [Remote clinical results in patients with prostatic carcinoma treated with hexestrol diphosphate]. | 1959 Nov-Dec |
|
| Clear-cell adenocarcinoma of the genital tract in young females. Registry report. | 1972 Dec 21 |
|
| Relationship of human liver dihydrodiol dehydrogenases to hepatic bile-acid-binding protein and an oxidoreductase of human colon cells. | 1996 Jan 15 |
|
| Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. | 1997 Mar |
|
| [Effects of veterinary drugs on beta-hexosaminidase release from rat basophilic leukemia cells (RBL-2H3)]. | 2002 Oct |
|
| Peritoneal lesions in guinea pigs treated with hormones. | 2002 Oct |
|
| Selective and potent inhibitors of human 20alpha-hydroxysteroid dehydrogenase (AKR1C1) that metabolizes neurosteroids derived from progesterone. | 2003 Feb 1 |
|
| Defined subcomplexes of the A1 ATPase from the archaeon Methanosarcina mazei Gö1: biochemical properties and redox regulation. | 2003 Jun 5 |
|
| Pharmacological inhibition of outwardly rectifying Cl- currents in rat peritoneal mast cells: a comparison of different stilbene derivatives. | 2003 Oct 8 |
|
| [Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals]. | 2004 Apr |
|
| A sol-gel method using acetic anhydride in the presence of cholesterol in organic solution media: preparation of silicas that recognize steroid hormones. | 2004 Apr 15 |
|
| Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types. | 2004 Jul |
|
| Formation of the depurinating N3adenine and N7guanine adducts by reaction of DNA with hexestrol-3',4'-quinone or enzyme-activated 3'-hydroxyhexestrol. Implications for a unifying mechanism of tumor initiation by natural and synthetic estrogens. | 2005 Jan |
|
| Separation of structurally related estrogens using isocratic elution pressurized capillary electrochromatography. | 2005 Oct 28 |
|
| Cellular and molecular regulation of the primate endometrium: a perspective. | 2006 |
|
| Molecular cloning of a novel type of rat cytoplasmic 17beta-hydroxysteroid dehydrogenase distinct from the type 5 isozyme. | 2006 Jun |
|
| Determination of hexoestrol residues in animal tissues based on enzyme-linked immunosorbent assay and comparison with liquid chromatography-tandem mass spectrometry. | 2006 Jun 7 |
|
| Enzymatic properties of a member (AKR1C20) of the aldo-keto reductase family. | 2006 Mar |
|
| Catechol quinones of estrogens in the initiation of breast, prostate, and other human cancers: keynote lecture. | 2006 Nov |
|
| 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. | 2006 Nov-Dec |
|
| Development and validation of a fluorescence HPLC-based screening assay for inhibition of human estrogen sulfotransferase. | 2006 Oct 1 |
|
| [Determination of residues of three stilbene drugs in animal tissues using gas chromatography-mass spectrometry]. | 2006 Sep |
|
| Activity of xenoestrogens at nanomolar concentrations in the E-Screen assay. | 2007 Dec |
|
| HPLC-tandem mass spectrometric method to characterize resveratrol metabolism in humans. | 2007 Feb |
|
| Interactions of diethylstilbestrol (DES) and DES analogs with membrane progestin receptor-alpha and the correlation with their nongenomic progestin activities. | 2007 Jul |
|
| A new molecularly imprinted polymer for the on-column solid-phase extraction of diethylstilbestrol from aqueous samples. | 2007 Jul |
|
| Simultaneous determination of residual stilbenes and stilbene metabolites in animal tissue by liquid chromatography-tandem mass spectrometry. | 2007 Jun 1 |
|
| 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 Mar-Apr |
|
| Determination of synthetic hormones in animal urine by high-performance liquid chromatography/mass spectrometry. | 2007 Mar-Apr |
|
| Studies on thermal reactivity of beta-(1,2-allenyl)butenolides and 2-allyl-3-allenylcyclohex-2-enones. | 2008 |
|
| Development and in-house validation of an LC-MS/MS method for the determination of stilbenes and resorcylic acid lactones in bovine urine. | 2008 Jun |
|
| Effects of hexestrol on mouse ovarian morphology and ovulation. | 2008 Jun 20 |
|
| [Hexestrol inhibits ATP-induced contractile response of isolated preparations of pregnant human uterus]. | 2008 Nov-Dec |
|
| Six-month depot formulation of leuprorelin acetate in the treatment of prostate cancer. | 2009 |
|
| Development of a rapid method for the analysis of synthetic growth promoters in bovine muscle using liquid chromatography tandem mass spectrometry. | 2009 Apr 1 |
|
| In silico identification of anthropogenic chemicals as ligands of zebrafish sex hormone binding globulin. | 2009 Jan 1 |
|
| Treatments for suppression of lactation. | 2009 Jan 21 |
|
| [Effects of Yi Fu Ning soft gelatin capsules on reproductive endocrine-immune function of ovariectomized rats]. | 2009 Jul |
|
| Towards high-throughput identification of endocrine disrupting compounds with mass spectrometry. | 2009 Jun |
|
| 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 Mar |
|
| Biochemical and structural characterization of a short-chain dehydrogenase/reductase of Thermus thermophilus HB8: a hyperthermostable aldose-1-dehydrogenase with broad substrate specificity. | 2009 Mar 16 |
|
| Characterization of a rat NADPH-dependent aldo-keto reductase (AKR1B13) induced by oxidative stress. | 2009 Mar 16 |
|
| [Determination of hormone multi-residues in animal tissues by gas chromatography-mass spectrometry]. | 2009 May |
|
| 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 Aug |
|
| Rational quantitative structure-activity relationship (RQSAR) screen for PXR and CAR isoform-specific nuclear receptor ligands. | 2010 Dec 5 |
|
| Diethylstilbestrol and other nonsteroidal estrogens: novel class of store-operated calcium channel modulators. | 2010 May |
|
| Endocrine disruption screening by protein and gene expression of vitellogenin in freshly isolated and cryopreserved rainbow trout hepatocytes. | 2014 Aug 18 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:05:09 GMT 2023
by
admin
on
Sat Dec 16 08:05:09 GMT 2023
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| Record UNII |
J9DFR4IT9Z
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| Record Status |
Validated (UNII)
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| Record Version |
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SUB02512MIG
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21123950
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100000086682
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20305-51-5
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Hexestrol dicaprylate
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J9DFR4IT9Z
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DTXSID50942446
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