DIENESTROL

US Previously Marketed

First approved in 1947

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

Structure Search

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+

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14102837
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
Estrogen receptor alpha 134 Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9048584	Agonist 2752		0.05 nM [Ki]
Estrogen receptor beta 113 Target ID: CHEMBL242 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9048584	Agonist 2752		0.03 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atrophic vaginitis 13 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14102837	Primary		Approved 8583	DIENESTROL Approved Use Unknown Launch Date 1947
Kraurosis vulvae 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10571841	Primary		Approved 8583	DIENESTROL Approved Use Unknown Launch Date 1947

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P004SFK
abcr GmbH	AB137538	http://www.abcr.com/shop/en/AB137538
ABI Chem	AC1NXGIT
ABI Chem	AC1Q2CAN
AK Scientific	7628AL
Ambinter	Amb22732971	http://www.ambinter.com/reference/22732971
AstaTech	T71379
BLD Pharm	BD124470	http://www.bldpharm.com/products/84-19-5.html
Combi-Blocks	QF-5428
DC Chemicals	DC38029	http://www.dcchemicals.com//product_show-Dienestrol_diacetate.html
eMolecules	50150015
eMolecules	511032
eNovation Chemicals	D760161
KeyOrganics	AS-72063
Lab Network	LN01740473
LGC Standards	DRE-C12598020	https://www.lgcstandards.com/US/en/p/DRE-C12598020
MolPort	MolPort-004-964-442
MuseChem	R058888
NCI Plated 2007	81279
NovoSeek	5805243
Smolecule	S526008	http://www.smolecule.com/products/s526008
Smolecule	S679072	https://www.smolecule.com/products/s679072
THE BioTek	bt-264491	https://www.thebiotek.com/product/inhibitors/bt-264491
Tractus	TR-031754
Wonderchem	WD06S3F
ZINC	ZINC000000608322	http://zinc15.docking.org/substances/ZINC000000608322

PubMed

Title	Date	PubMed
Amelioration of sexual adverse effects in the early breast cancer patient.	2010-09	20602189
Synthetic studies on schisandra nortriterpenoids. Stereocontrolled synthesis of enantiopure C-5-epi ABC ring systems of micrandilactone A and lancifodilactone G using RCM.	2010-06-18	20491457
Comparison of murine and human estrogen sulfotransferase inhibition in vitro and in silico--implications for differences in activity, subunit dimerization and substrate inhibition.	2010-04-12	20025931
Synthesis and applications of diethylstilbestrol-based molecularly imprinted polymer-coated hollow fiber tube.	2010-03-17	20172093
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.	2010-02-10	20041659
Role of water in the multifaceted catalytic antibody 4B2 for allylic isomerization and Kemp elimination reactions.	2009-11-19	19860435
Ability of Group IVB metallocene polyethers containing dienestrol to arrest the growth of selected cancer cell lines.	2009-10-07	19811643
Quantitative screening of stilbenes and zeranol and its related residues and natural precursors in veal liver by gas chromatography-mass spectrometry.	2009-08-12	19722563
Determination of anabolic steroids in bovine urine by liquid chromatography-tandem mass spectrometry.	2009-08-01	19375394
[Determination of hormone multi-residues in animal tissues by gas chromatography-mass spectrometry].	2009-05	19803132
Interventions for psychosexual dysfunction in women treated for gynaecological malignancy.	2009-04-15	19370605
Development of a rapid method for the analysis of synthetic growth promoters in bovine muscle using liquid chromatography tandem mass spectrometry.	2009-04-01	19286019
Mechanism of metabolic activation and DNA adduct formation by the human carcinogen diethylstilbestrol: the defining link to natural estrogens.	2009-03-15	19089919
A short access to 3-hydroxy-4-hydroxymethyltetrahydrofurans: application to the total synthesis of amphiasterin B4.	2009-03-06	19199668
Total synthesis and structural confirmation of brevisamide, a new marine cyclic ether alkaloid from the dinoflagellate Karenia brevis.	2009-01-01	19067558
Potential use of an estrogen-glucocorticoid receptor chimera as a drug screen for tissue selective estrogenic activity.	2009-01	18976723
Total synthesis of spirotenuipesines A and B.	2008-12-19	18973385
Total synthesis of (-)-pseudolaric acid B.	2008-12-03	18998641
Stereoselective preparation of dienol phosphates from alpha,beta-ethylenic aldehydes.	2008-09-05	18646858
Efficient preparation of terminal conjugated dienes by coupling of dienol phosphates with grignard reagents under iron catalysis.	2008-06-19	18476715
Development and in-house validation of an LC-MS/MS method for the determination of stilbenes and resorcylic acid lactones in bovine urine.	2008-06	18363048
[Role of insufficient hormone production in development of osteopenia in consequence of physical loads defficiency].	2008-03-21	18350830
Determination of estrogens in wastewater using three-phase hollow fiber-mediated liquid-phase microextraction followed by HPLC.	2008-03	18275104
Role of androgens, progestins and tibolone in the treatment of menopausal symptoms: a review of the clinical evidence.	2008	18488873
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	18338409
Activity of xenoestrogens at nanomolar concentrations in the E-Screen assay.	2007-12	18174956
Management of sexual dysfunction in postmenopausal breast cancer patients taking adjuvant aromatase inhibitor therapy.	2007-12	18087605
Pulsed field ionization electron spectroscopy and molecular structure of aluminum uracil.	2007-10-25	17914779
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.	2007-10-23	17902707
Simultaneous determination of residual stilbenes and stilbene metabolites in animal tissue by liquid chromatography-tandem mass spectrometry.	2007-06-01	17452030
Determination of synthetic hormones in animal urine by high-performance liquid chromatography/mass spectrometry.	2007-05-04	17474533
Novel approaches to the analysis of steroid estrogens in river sediments.	2007-02	17219098
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.	2007-01-16	17217168
Catalytic role for arginine 188 in the C-C hydrolase catalytic mechanism for Escherichia coli MhpC and Burkholderia xenovorans LB400 BphD.	2006-10-17	17029402
Development and validation of a fluorescence HPLC-based screening assay for inhibition of human estrogen sulfotransferase.	2006-10-01	16914110
[Determination of residues of three stilbene drugs in animal tissues using gas chromatography-mass spectrometry].	2006-09	17165538
Caging effects on the ground and excited states of 2,2'-bipyridine-3,3'-diol embedded in cyclodextrins.	2006-06-29	16789770
Evolution of enzymatic activity in the tautomerase superfamily: mechanistic and structural consequences of the L8R mutation in 4-oxalocrotonate tautomerase.	2006-06-27	16784221
[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].	2006-03-16	16536031
Separation of structurally related estrogens using isocratic elution pressurized capillary electrochromatography.	2005-10-28	16199236
Catalytic, enantioselective, vinylogous aldol reactions.	2005-07-25	15940727
On-line coupling of pressurized capillary electrochromatography with end-column amperometric detection for analysis of estrogens.	2005-06	15920782
On the Diels-Alder reactions of pentadienyl maleates and citraconates.	2005-04-07	15785820
Synthesis of the catechols of natural and synthetic estrogens by using 2-iodoxybenzoic acid (IBX) as the oxidizing agent.	2005-03	15763595
Catalytic mechanism of C-C hydrolase MhpC from Escherichia coli: kinetic analysis of His263 and Ser110 site-directed mutants.	2005-02-11	15663941
Metal carbene-promoted sequential transformations for the enantioselective synthesis of highly functionalized cycloheptadienes.	2005-02-09	15686344
Highly diastereoselective tandem photoenolization-hetero-Diels-Alder cycloaddition reactions of o-tolualdehydes in the solid state.	2004-11-26	15549821
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.	2004-07	15276617
Total syntheses of sesterpenic acids: refuted (+/-)-bilosespenes A and B.	2003-11-27	14627429
Serum levels of insulin-like growth factor-I, IGF-binding protein 1 and 3, and insulin and endometrial cancer risk.	2003-11-03	14583772

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 Created by `admin` on `Mon Mar 31 17:46:24 GMT 2025` Edited by `admin` on `Mon Mar 31 17:46:24 GMT 2025`
Record UNII	RRW32X4U1F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIENESTROL

Official Name

English

CYCLADIENE

Preferred Name

English

RESTROL

Brand Name

English

GYNEFOLLIN

Brand Name

English

DIENESTROL [VANDF]

Common Name

English

DIENESTROL [HSDB]

Common Name

English

NSC-59809

Code

English

OESTRORAL

Brand Name

English

OESTRASID

Brand Name

English

FOLLIDIENE

Brand Name

English

PHENOL, 4,4'-(1,2-DIETHYLIDENE-1,2-ETHANEDIYL)BIS-, (E,E)

Common Name

English

ESTRAGARD

Brand Name

English

DIENESTROL [USP IMPURITY]

Common Name

English

DV

Brand Name

English

HORMOFEMIN

Brand Name

English

Dienestrol [WHO-DD]

Common Name

English

DIENOL

Brand Name

English

OESTRODIENE

Brand Name

English

.ALPHA.-DIENESTROL DIACETATE

Common Name

English

DIENESTROL [EP IMPURITY]

Common Name

English

DIENESTROL, .ALPHA.-

Common Name

English

(E,E)-4,4'-(DIETHYLIDENEETHYLENE)DIPHENOL

Systematic Name

English

RETALON

Brand Name

English

DIENESTROL [ORANGE BOOK]

Common Name

English

dienestrol [INN]

Common Name

English

SYNESTROL

Brand Name

English

DIENOESTROL

Common Name

English

ESTRAGUARD

Brand Name

English

ESTRORAL

Brand Name

English

DIENESTROL [MI]

Common Name

English

DIENESTROL [MART.]

Common Name

English

DEHYDROSTILBESTROL

Brand Name

English

DIENESTROL TRANS-FORM [MI]

Common Name

English

DIENESTROL DIACETATE, .ALPHA.-

Common Name

English

DINOVEX

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QG03CC02