Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H18O2 |
| Molecular Weight | 266.3343 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C\C=C(C1=CC=C(O)C=C1)\C(=C\C)C2=CC=C(O)C=C2
InChI
InChIKey=NFDFQCUYFHCNBW-SCGPFSFSSA-N
InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+
| Molecular Formula | C18H18O2 |
| Molecular Weight | 266.3343 |
| 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 |
|---|---|---|
| Cardiovascular birth defects and antenatal exposure to female sex hormones. | 1977 Jan 13 |
|
| 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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| Repellent activity of estrogenic compounds toward zoospores of the phytopathogenic fungus Aphanomyces cochlioides. | 2001 Mar-Apr |
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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 |
|
| Evolution of the vinylogous Mannich reaction as a key construction for alkaloid synthesis. | 2002 Oct |
|
| Defined subcomplexes of the A1 ATPase from the archaeon Methanosarcina mazei Gö1: biochemical properties and redox regulation. | 2003 Jun 5 |
|
| 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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| On-line coupling of pressurized capillary electrochromatography with end-column amperometric detection for analysis of estrogens. | 2005 Jun |
|
| Synthesis of the catechols of natural and synthetic estrogens by using 2-iodoxybenzoic acid (IBX) as the oxidizing agent. | 2005 Mar |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| 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 |
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
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| Record UNII |
RRW32X4U1F
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Validated (UNII)
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QG03CC02
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NCI_THESAURUS |
C2182
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