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 |
|---|---|---|
| Amelioration of sexual adverse effects in the early breast cancer patient. | 2010-09 |
|
| Synthetic studies on schisandra nortriterpenoids. Stereocontrolled synthesis of enantiopure C-5-epi ABC ring systems of micrandilactone A and lancifodilactone G using RCM. | 2010-06-18 |
|
| Comparison of murine and human estrogen sulfotransferase inhibition in vitro and in silico--implications for differences in activity, subunit dimerization and substrate inhibition. | 2010-04-12 |
|
| Synthesis and applications of diethylstilbestrol-based molecularly imprinted polymer-coated hollow fiber tube. | 2010-03-17 |
|
| 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. | 2010-02-10 |
|
| Role of water in the multifaceted catalytic antibody 4B2 for allylic isomerization and Kemp elimination reactions. | 2009-11-19 |
|
| Ability of Group IVB metallocene polyethers containing dienestrol to arrest the growth of selected cancer cell lines. | 2009-10-07 |
|
| Quantitative screening of stilbenes and zeranol and its related residues and natural precursors in veal liver by gas chromatography-mass spectrometry. | 2009-08-12 |
|
| Determination of anabolic steroids in bovine urine by liquid chromatography-tandem mass spectrometry. | 2009-08-01 |
|
| [Determination of hormone multi-residues in animal tissues by gas chromatography-mass spectrometry]. | 2009-05 |
|
| Interventions for psychosexual dysfunction in women treated for gynaecological malignancy. | 2009-04-15 |
|
| Development of a rapid method for the analysis of synthetic growth promoters in bovine muscle using liquid chromatography tandem mass spectrometry. | 2009-04-01 |
|
| Mechanism of metabolic activation and DNA adduct formation by the human carcinogen diethylstilbestrol: the defining link to natural estrogens. | 2009-03-15 |
|
| A short access to 3-hydroxy-4-hydroxymethyltetrahydrofurans: application to the total synthesis of amphiasterin B4. | 2009-03-06 |
|
| Total synthesis and structural confirmation of brevisamide, a new marine cyclic ether alkaloid from the dinoflagellate Karenia brevis. | 2009-01-01 |
|
| Potential use of an estrogen-glucocorticoid receptor chimera as a drug screen for tissue selective estrogenic activity. | 2009-01 |
|
| Total synthesis of spirotenuipesines A and B. | 2008-12-19 |
|
| Total synthesis of (-)-pseudolaric acid B. | 2008-12-03 |
|
| Stereoselective preparation of dienol phosphates from alpha,beta-ethylenic aldehydes. | 2008-09-05 |
|
| Efficient preparation of terminal conjugated dienes by coupling of dienol phosphates with grignard reagents under iron catalysis. | 2008-06-19 |
|
| 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 |
|
| [Role of insufficient hormone production in development of osteopenia in consequence of physical loads defficiency]. | 2008-03-21 |
|
| Determination of estrogens in wastewater using three-phase hollow fiber-mediated liquid-phase microextraction followed by HPLC. | 2008-03 |
|
| Role of androgens, progestins and tibolone in the treatment of menopausal symptoms: a review of the clinical evidence. | 2008 |
|
| Synthetic scope of Ru(OH)x/Al2O3-catalyzed hydrogen-transfer reactions: an application to reduction of allylic alcohols by a sequential process of isomerization/Meerwein-Ponndorf-Verley-type reduction. | 2008 |
|
| Activity of xenoestrogens at nanomolar concentrations in the E-Screen assay. | 2007-12 |
|
| Management of sexual dysfunction in postmenopausal breast cancer patients taking adjuvant aromatase inhibitor therapy. | 2007-12 |
|
| Pulsed field ionization electron spectroscopy and molecular structure of aluminum uracil. | 2007-10-25 |
|
| Kinetic and stereochemical analysis of YwhB, a 4-oxalocrotonate tautomerase homologue in Bacillus subtilis: mechanistic implications for the YwhB- and 4-oxalocrotonate tautomerase-catalyzed reactions. | 2007-10-23 |
|
| 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 |
|
| Novel approaches to the analysis of steroid estrogens in river sediments. | 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 |
|
| Catalytic role for arginine 188 in the C-C hydrolase catalytic mechanism for Escherichia coli MhpC and Burkholderia xenovorans LB400 BphD. | 2006-10-17 |
|
| Development and validation of a fluorescence HPLC-based screening assay for inhibition of human estrogen sulfotransferase. | 2006-10-01 |
|
| [Determination of residues of three stilbene drugs in animal tissues using gas chromatography-mass spectrometry]. | 2006-09 |
|
| Caging effects on the ground and excited states of 2,2'-bipyridine-3,3'-diol embedded in cyclodextrins. | 2006-06-29 |
|
| Evolution of enzymatic activity in the tautomerase superfamily: mechanistic and structural consequences of the L8R mutation in 4-oxalocrotonate tautomerase. | 2006-06-27 |
|
| [Functional state of calcitonin-producing cells of the female rats' thyroid as a result of experimental osteopenia therapy by graduated support loading combined with oestrogens and calcitonin injection]. | 2006-03-16 |
|
| Separation of structurally related estrogens using isocratic elution pressurized capillary electrochromatography. | 2005-10-28 |
|
| Catalytic, enantioselective, vinylogous aldol reactions. | 2005-07-25 |
|
| On-line coupling of pressurized capillary electrochromatography with end-column amperometric detection for analysis of estrogens. | 2005-06 |
|
| On the Diels-Alder reactions of pentadienyl maleates and citraconates. | 2005-04-07 |
|
| Synthesis of the catechols of natural and synthetic estrogens by using 2-iodoxybenzoic acid (IBX) as the oxidizing agent. | 2005-03 |
|
| Catalytic mechanism of C-C hydrolase MhpC from Escherichia coli: kinetic analysis of His263 and Ser110 site-directed mutants. | 2005-02-11 |
|
| Metal carbene-promoted sequential transformations for the enantioselective synthesis of highly functionalized cycloheptadienes. | 2005-02-09 |
|
| Highly diastereoselective tandem photoenolization-hetero-Diels-Alder cycloaddition reactions of o-tolualdehydes in the solid state. | 2004-11-26 |
|
| 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. | 2004-07 |
|
| Total syntheses of sesterpenic acids: refuted (+/-)-bilosespenes A and B. | 2003-11-27 |
|
| Serum levels of insulin-like growth factor-I, IGF-binding protein 1 and 3, and insulin and endometrial cancer risk. | 2003-11-03 |
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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on
Edited
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| Record UNII |
D20D148WPQ
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| Record Status |
Validated (UNII)
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201-520-2
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24705-61-1
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Dienestrol diacetate
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m4385
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