U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of DIENESTROL

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
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

Sources: Dodds et al., Proc. Roy. Soc. 127B, 162 (1939)

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.05 nM [Ki]
0.03 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DIENESTROL

Approved Use

Unknown

Launch Date

-7.2515518E11
Primary
DIENESTROL

Approved Use

Unknown

Launch Date

-7.2515518E11
PubMed

PubMed

TitleDatePubMed
Vaginal cancer after maternal treatment with synthetic estrogens.
1971 Aug 12
Clear-cell adenocarcinoma of the genital tract in young females. Registry report.
1972 Dec 21
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
Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta.
1997 Mar
Evolution of the vinylogous Mannich reaction as a key construction for alkaloid synthesis.
2002 Oct
Peritoneal lesions in guinea pigs treated with hormones.
2002 Oct
Diethylstilbestrol and tetrahydrochrysenes are calcium channel blockers in human platelets: relationship to the stilbene pharmacophore.
2003 Apr 15
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
Defined subcomplexes of the A1 ATPase from the archaeon Methanosarcina mazei Gö1: biochemical properties and redox regulation.
2003 Jun 5
Serum levels of insulin-like growth factor-I, IGF-binding protein 1 and 3, and insulin and endometrial cancer risk.
2003 Nov 3
Effects of environmental estrogenic chemicals on AP1 mediated transcription with estrogen receptors alpha and beta.
2004 Jan
On the Diels-Alder reactions of pentadienyl maleates and citraconates.
2005 Apr 7
Catalytic mechanism of C-C hydrolase MhpC from Escherichia coli: kinetic analysis of His263 and Ser110 site-directed mutants.
2005 Feb 11
Metal carbene-promoted sequential transformations for the enantioselective synthesis of highly functionalized cycloheptadienes.
2005 Feb 9
Catalytic, enantioselective, vinylogous aldol reactions.
2005 Jul 25
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
[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].
2005 Nov-Dec
Separation of structurally related estrogens using isocratic elution pressurized capillary electrochromatography.
2005 Oct 28
Evolution of enzymatic activity in the tautomerase superfamily: mechanistic and structural consequences of the L8R mutation in 4-oxalocrotonate tautomerase.
2006 Jun 27
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
Development and validation of a fluorescence HPLC-based screening assay for inhibition of human estrogen sulfotransferase.
2006 Oct 1
Catalytic role for arginine 188 in the C-C hydrolase catalytic mechanism for Escherichia coli MhpC and Burkholderia xenovorans LB400 BphD.
2006 Oct 17
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
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
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
Determination of anabolic steroids in bovine urine by liquid chromatography-tandem mass spectrometry.
2009 Aug 1
Potential use of an estrogen-glucocorticoid receptor chimera as a drug screen for tissue selective estrogenic activity.
2009 Jan
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
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
Synthesis and applications of diethylstilbestrol-based molecularly imprinted polymer-coated hollow fiber tube.
2010 Mar 17
Amelioration of sexual adverse effects in the early breast cancer patient.
2010 Sep
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
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
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 Fri Dec 15 15:05:57 UTC 2023
Edited
by admin
on Fri Dec 15 15:05:57 UTC 2023
Record UNII
RRW32X4U1F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIENESTROL
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
INN  
Official 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
CYCLADIENE
Brand 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
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
NCI_THESAURUS C2182
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
WHO-ATC G03CC02
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
LIVERTOX 301
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
WHO-VATC QG03CB01
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
WHO-ATC G03CB01
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
Code System Code Type Description
EVMPD
SUB07107MIG
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
NSC
59809
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
ChEMBL
CHEMBL1018
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
CHEBI
4518
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
IUPHAR
7160
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-519-7
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
NCI_THESAURUS
C65377
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
DRUG CENTRAL
870
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
DRUG BANK
DB00890
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
PUBCHEM
667476
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
CAS
13029-44-2
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
SMS_ID
100000082943
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
MERCK INDEX
m4385
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY Merck Index
MESH
D004028
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
CAS
84-17-3
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
FDA UNII
RRW32X4U1F
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
WIKIPEDIA
DIENESTROL
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
HSDB
84-17-3
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
RXCUI
3368
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY RxNorm
INN
1523
Created by admin on Fri Dec 15 15:05:57 UTC 2023 , Edited by admin on Fri Dec 15 15:05:57 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY