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+
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL206 |
0.05 nM [Ki] | ||
Target ID: CHEMBL242 |
0.03 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | DIENESTROL Approved UseUnknown Launch Date-7.2515518E11 |
|||
| Primary | DIENESTROL Approved UseUnknown Launch Date-7.2515518E11 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Vaginal cancer after maternal treatment with synthetic estrogens. | 1971 Aug 12 |
|
| 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 |
|
| 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 |
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| Validation of screening method for residues of diethylstilbestrol, dienestrol, hexestrol, and zeranol in bovine urine using immunoaffinity chromatography and gas chromatography/mass spectrometry. | 2003 Jul-Aug |
|
| Total syntheses of sesterpenic acids: refuted (+/-)-bilosespenes A and B. | 2003 Nov 27 |
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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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| Catalytic mechanism of C-C hydrolase MhpC from Escherichia coli: kinetic analysis of His263 and Ser110 site-directed mutants. | 2005 Feb 11 |
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| Synthesis of the catechols of natural and synthetic estrogens by using 2-iodoxybenzoic acid (IBX) as the oxidizing agent. | 2005 Mar |
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| Development and validation of a fluorescence HPLC-based screening assay for inhibition of human estrogen sulfotransferase. | 2006 Oct 1 |
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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 |
|
| Activity of xenoestrogens at nanomolar concentrations in the E-Screen assay. | 2007 Dec |
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| Management of sexual dysfunction in postmenopausal breast cancer patients taking adjuvant aromatase inhibitor therapy. | 2007 Dec |
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| 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 (-)-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 |
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| Potential use of an estrogen-glucocorticoid receptor chimera as a drug screen for tissue selective estrogenic activity. | 2009 Jan |
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| Total synthesis and structural confirmation of brevisamide, a new marine cyclic ether alkaloid from the dinoflagellate Karenia brevis. | 2009 Jan 1 |
|
| [Determination of hormone multi-residues in animal tissues by gas chromatography-mass spectrometry]. | 2009 May |
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| 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 |
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| Synthesis and applications of diethylstilbestrol-based molecularly imprinted polymer-coated hollow fiber tube. | 2010 Mar 17 |
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| Amelioration of sexual adverse effects in the early breast cancer patient. | 2010 Sep |
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| 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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WHO-VATC |
QG03CC02
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NCI_THESAURUS |
C2182
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WHO-ATC |
G03CC02
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LIVERTOX |
301
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QG03CB01
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G03CB01
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84-17-3
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ACTIVE MOIETY
