Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C22H22O4 |
| Molecular Weight | 350.4077 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C\C=C(C1=CC=C(OC(C)=O)C=C1)\C(=C\C)C2=CC=C(OC(C)=O)C=C2
InChI
InChIKey=YWLLGDVBTLPARJ-OXAZHYLESA-N
InChI=1S/C22H22O4/c1-5-21(17-7-11-19(12-8-17)25-15(3)23)22(6-2)18-9-13-20(14-10-18)26-16(4)24/h5-14H,1-4H3/b21-5+,22-6+
| Molecular Formula | C22H22O4 |
| Molecular Weight | 350.4077 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
http://www.kiessig.com/drugs/druginfo.aspx?id=652 | https://www.ncbi.nlm.nih.gov/pubmed/2928320 | https://www.ncbi.nlm.nih.gov/pubmed/8794418
Curator's Comment: description was created based on several sources, including
http://www.kiessig.com/drugs/druginfo.aspx?id=652 | https://www.ncbi.nlm.nih.gov/pubmed/2928320 | https://www.ncbi.nlm.nih.gov/pubmed/8794418
Dienestrol (INN, USAN) (brand names Ortho Dienestrol, Dienoestrol, Dienoestrol Ortho, Sexadien, Denestrolin, Dienol, Dinovex, Follormon, Oestrodiene, Synestrol, numerous others) is a synthetic, non-steroidal estrogen. It is an estrogen receptor agonist. Estrogens work partly by increasing a normal clear discharge from the vagina and making the vulva and urethra healthy. Using or applying an estrogen relieves or lessens: dryness and soreness in the vagina, itching, redness, or soreness of the vulva. Conditions that are treated with vaginal estrogens include a genital skin condition (vulvar atrophy), inflammation of the vagina (atrophic vaginitis), and inflammation of the urethra (atrophic urethritis). Dienestrol currently discontinued in US, but still in market in some other counties
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Vaginal cancer after maternal treatment with synthetic estrogens. | 1971 Aug 12 |
|
| Clear-cell adenocarcinoma of the genital tract in young females. Registry report. | 1972 Dec 21 |
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| Cardiovascular birth defects and antenatal exposure to female sex hormones. | 1977 Jan 13 |
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| Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. | 1997 Mar |
|
| Overproduction of a functional A1 ATPase from the archaeon Methanosarcina mazei Gö1 in Escherichia coli. | 2001 Jul |
|
| Evolution of the vinylogous Mannich reaction as a key construction for alkaloid synthesis. | 2002 Oct |
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| On-line coupling of pressurized capillary electrochromatography with end-column amperometric detection for analysis of estrogens. | 2005 Jun |
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| Synthesis of the catechols of natural and synthetic estrogens by using 2-iodoxybenzoic acid (IBX) as the oxidizing agent. | 2005 Mar |
|
| Evolution of enzymatic activity in the tautomerase superfamily: mechanistic and structural consequences of the L8R mutation in 4-oxalocrotonate tautomerase. | 2006 Jun 27 |
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| 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 |
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| Development and validation of a fluorescence HPLC-based screening assay for inhibition of human estrogen sulfotransferase. | 2006 Oct 1 |
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| Novel approaches to the analysis of steroid estrogens in river sediments. | 2007 Feb |
|
| [Role of insufficient hormone production in development of osteopenia in consequence of physical loads defficiency]. | 2007 Nov-Dec |
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| Efficient preparation of terminal conjugated dienes by coupling of dienol phosphates with grignard reagents under iron catalysis. | 2008 Jun 19 |
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| Determination of estrogens in wastewater using three-phase hollow fiber-mediated liquid-phase microextraction followed by HPLC. | 2008 Mar |
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| Quantitative screening of stilbenes and zeranol and its related residues and natural precursors in veal liver by gas chromatography-mass spectrometry. | 2009 Aug 12 |
|
| Potential use of an estrogen-glucocorticoid receptor chimera as a drug screen for tissue selective estrogenic activity. | 2009 Jan |
|
| Total synthesis and structural confirmation of brevisamide, a new marine cyclic ether alkaloid from the dinoflagellate Karenia brevis. | 2009 Jan 1 |
|
| Towards high-throughput identification of endocrine disrupting compounds with mass spectrometry. | 2009 Jun |
|
| Mechanism of metabolic activation and DNA adduct formation by the human carcinogen diethylstilbestrol: the defining link to natural estrogens. | 2009 Mar 15 |
|
| Role of water in the multifaceted catalytic antibody 4B2 for allylic isomerization and Kemp elimination reactions. | 2009 Nov 19 |
|
| Ability of Group IVB metallocene polyethers containing dienestrol to arrest the growth of selected cancer cell lines. | 2009 Oct 7 |
|
| Comparison of murine and human estrogen sulfotransferase inhibition in vitro and in silico--implications for differences in activity, subunit dimerization and substrate inhibition. | 2010 Apr 12 |
|
| Improved synthesis of (3E,6Z,9Z)-1,3,6,9-nonadecatetraene, attraction inhibitor of bruce spanworm, Operophtera bruceata, to pheromone traps for monitoring winter moth, Operophtera brumata. | 2010 Feb 10 |
|
| Synthetic studies on schisandra nortriterpenoids. Stereocontrolled synthesis of enantiopure C-5-epi ABC ring systems of micrandilactone A and lancifodilactone G using RCM. | 2010 Jun 18 |
|
| Synthesis and applications of diethylstilbestrol-based molecularly imprinted polymer-coated hollow fiber tube. | 2010 Mar 17 |
|
| FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013 Sep 5 |
Patents
Sample Use Guides
The usual dosage range is one or two applicatorsful per day for one or two weeks, then gradually reduced to one half initial dosage for a similar period. A maintenance dosage of one applicatorful, one to three times a week, may be used after restoration of the vaginal mucosa has been achieved. The lowest dose that will control symptoms should be chosen and medication should be discontinued as promptly as possible. Attempts to discontinue or taper medication should be made at 3 to 6-month intervals.
Route of Administration:
Vaginal
Renal tubular cells were grown on a PF-HR-9 basement membrane under serum-free chemically defined culture conditions in the absence or presence of Dienestrol (as a solution in ethanol). Effect of Estrogens and Nonestrogenic Hormones on Cell Outgrowth was assayed at 5, 7, 11, and 14 days.
| Substance Class |
Chemical
Created
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D20D148WPQ
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Validated (UNII)
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Dienestrol diacetate
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