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-CMDWGMEOSA-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 |
|---|---|---|
| Stable expression of a human liver UDP-glucuronosyltransferase (UGT2B15) with activity toward steroid and xenobiotic substrates. | 1994 Sep-Oct |
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| Colour reactions of PH. EUR. for identification of drugs using 1,3-dibromo-5,5-dimethylhydantoin (DBH) instead of elemental bromine. Analytical methods of pharmacopoeias with DBH in respect to environmental and economical concern, Part 10. | 2002 Mar |
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| Total syntheses of sesterpenic acids: refuted (+/-)-bilosespenes A and B. | 2003 Nov 27 |
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| 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 |
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| Highly diastereoselective tandem photoenolization-hetero-Diels-Alder cycloaddition reactions of o-tolualdehydes in the solid state. | 2004 Nov 26 |
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| Metal carbene-promoted sequential transformations for the enantioselective synthesis of highly functionalized cycloheptadienes. | 2005 Feb 9 |
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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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| Separation of structurally related estrogens using isocratic elution pressurized capillary electrochromatography. | 2005 Oct 28 |
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| Caging effects on the ground and excited states of 2,2'-bipyridine-3,3'-diol embedded in cyclodextrins. | 2006 Jun 29 |
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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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| Novel approaches to the analysis of steroid estrogens in river sediments. | 2007 Feb |
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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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| 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 |
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| 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 |
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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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| Stereoselective preparation of dienol phosphates from alpha,beta-ethylenic aldehydes. | 2008 Sep 5 |
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| Interventions for psychosexual dysfunction in women treated for gynaecological malignancy. | 2009 Apr 15 |
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| Determination of anabolic steroids in bovine urine by liquid chromatography-tandem mass spectrometry. | 2009 Aug 1 |
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| Towards high-throughput identification of endocrine disrupting compounds with mass spectrometry. | 2009 Jun |
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| 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 |
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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SUBSTANCE RECORD
