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+
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 |
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| 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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| Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates. | 1994 Sep-Oct |
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| Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. | 1997 Mar |
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| Effects of environmental estrogenic chemicals on AP1 mediated transcription with estrogen receptors alpha and beta. | 2004 Jan |
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| [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]. | 2005 Nov-Dec |
|
| Separation of structurally related estrogens using isocratic elution pressurized capillary electrochromatography. | 2005 Oct 28 |
|
| Evolution of enzymatic activity in the tautomerase superfamily: mechanistic and structural consequences of the L8R mutation in 4-oxalocrotonate tautomerase. | 2006 Jun 27 |
|
| Caging effects on the ground and excited states of 2,2'-bipyridine-3,3'-diol embedded in cyclodextrins. | 2006 Jun 29 |
|
| 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 |
|
| Catalytic role for arginine 188 in the C-C hydrolase catalytic mechanism for Escherichia coli MhpC and Burkholderia xenovorans LB400 BphD. | 2006 Oct 17 |
|
| [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 |
|
| Management of sexual dysfunction in postmenopausal breast cancer patients taking adjuvant aromatase inhibitor therapy. | 2007 Dec |
|
| Novel approaches to the analysis of steroid estrogens in river sediments. | 2007 Feb |
|
| Simultaneous determination of residual stilbenes and stilbene metabolites in animal tissue by liquid chromatography-tandem mass spectrometry. | 2007 Jun 1 |
|
| Determination of synthetic hormones in animal urine by high-performance liquid chromatography/mass spectrometry. | 2007 Mar-Apr |
|
| [Role of insufficient hormone production in development of osteopenia in consequence of physical loads defficiency]. | 2007 Nov-Dec |
|
| 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 Oct 23 |
|
| Pulsed field ionization electron spectroscopy and molecular structure of aluminum uracil. | 2007 Oct 25 |
|
| 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 |
|
| Total synthesis of spirotenuipesines A and B. | 2008 Dec 19 |
|
| Total synthesis of (-)-pseudolaric acid B. | 2008 Dec 3 |
|
| 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 |
|
| Efficient preparation of terminal conjugated dienes by coupling of dienol phosphates with grignard reagents under iron catalysis. | 2008 Jun 19 |
|
| Determination of estrogens in wastewater using three-phase hollow fiber-mediated liquid-phase microextraction followed by HPLC. | 2008 Mar |
|
| Stereoselective preparation of dienol phosphates from alpha,beta-ethylenic aldehydes. | 2008 Sep 5 |
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| Development of a rapid method for the analysis of synthetic growth promoters in bovine muscle using liquid chromatography tandem mass spectrometry. | 2009 Apr 1 |
|
| Interventions for psychosexual dysfunction in women treated for gynaecological malignancy. | 2009 Apr 15 |
|
| Determination of anabolic steroids in bovine urine by liquid chromatography-tandem mass spectrometry. | 2009 Aug 1 |
|
| 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 |
|
| A short access to 3-hydroxy-4-hydroxymethyltetrahydrofurans: application to the total synthesis of amphiasterin B4. | 2009 Mar 6 |
|
| [Determination of hormone multi-residues in animal tissues by gas chromatography-mass spectrometry]. | 2009 May |
|
| 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 |
|
| Amelioration of sexual adverse effects in the early breast cancer patient. | 2010 Sep |
|
| Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities. | 2012 Nov 19 |
|
| FDA-approved drugs and other compounds tested as inhibitors of human glutathione transferase P1-1. | 2013 Sep 5 |
|
| Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein. | 2015 Feb |
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.
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Dienestrol diacetate
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m4385
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ACTIVE MOIETY
SUBSTANCE RECORD
