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 |
|---|---|---|
| Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. | 1997 Mar |
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| Evolution of the vinylogous Mannich reaction as a key construction for alkaloid synthesis. | 2002 Oct |
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| Activation enthalpies and entropies for the microscopic rate constants of acetate-catalyzed isomerization of 5-androstene-3,17-dione. | 2003 Aug 27 |
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| Defined subcomplexes of the A1 ATPase from the archaeon Methanosarcina mazei Gö1: biochemical properties and redox regulation. | 2003 Jun 5 |
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| Total syntheses of sesterpenic acids: refuted (+/-)-bilosespenes A and B. | 2003 Nov 27 |
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| On the Diels-Alder reactions of pentadienyl maleates and citraconates. | 2005 Apr 7 |
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| Catalytic, enantioselective, vinylogous aldol reactions. | 2005 Jul 25 |
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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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| Catalytic role for arginine 188 in the C-C hydrolase catalytic mechanism for Escherichia coli MhpC and Burkholderia xenovorans LB400 BphD. | 2006 Oct 17 |
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| [Determination of residues of three stilbene drugs in animal tissues using gas chromatography-mass spectrometry]. | 2006 Sep |
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| Activity of xenoestrogens at nanomolar concentrations in the E-Screen assay. | 2007 Dec |
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| Simultaneous determination of residual stilbenes and stilbene metabolites in animal tissue by liquid chromatography-tandem mass spectrometry. | 2007 Jun 1 |
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| Determination of synthetic hormones in animal urine by high-performance liquid chromatography/mass spectrometry. | 2007 Mar-Apr |
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| [Role of insufficient hormone production in development of osteopenia in consequence of physical loads defficiency]. | 2007 Nov-Dec |
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| 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 |
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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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| Development of a rapid method for the analysis of synthetic growth promoters in bovine muscle using liquid chromatography tandem mass spectrometry. | 2009 Apr 1 |
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| Determination of anabolic steroids in bovine urine by liquid chromatography-tandem mass spectrometry. | 2009 Aug 1 |
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| Mechanism of metabolic activation and DNA adduct formation by the human carcinogen diethylstilbestrol: the defining link to natural estrogens. | 2009 Mar 15 |
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| 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 |
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| Ability of Group IVB metallocene polyethers containing dienestrol to arrest the growth of selected cancer cell lines. | 2009 Oct 7 |
|
| 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
