Page last updated: 2024-11-10

dimethylstilbestrol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

dimethylstilbestrol: stilbene derivative with anti-estrogenic & anti-fertility activities; minor descriptor (75-85); on-line & Index Medicus search STILBENES (75-85); RN given refers to cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3004636
CHEMBL ID269003
CHEBI ID34717
SCHEMBL ID125634
SCHEMBL ID125635
MeSH IDM0262892

Synonyms (42)

Synonym
4,4'-(2e)-but-2-ene-2,3-diyldiphenol
4-[(e)-2-(4-hydroxyphenyl)-1-methyl-prop-1-enyl]phenol
dimethylstibestrol
BIDD:ER0155
30l22q8n9m ,
unii-30l22q8n9m
4, trans-.alpha.,.alpha.'-dimethyl-
4,2-dimethyl-1,2-ethenediyl)bis(phenol) (e)-
nsc-45946
dimethylstilbesterol
dimethylstilbestrol
nsc45946
.alpha.,4'-stilbenediol (e)-
552-80-7
4, .alpha.,.alpha.'-dimethyl-, (e)-
phenol,4'-(1,2-dimethyl-1,2-ethenediyl)bis-, (e)-
nsc-658943
nsc658943
(e)-4,4'-(1,2-dimethyl-1,2-ethenediyl)bisphenol
alpha,alpha'-dimethyl-4,4'-stilbenediol (e)-
ai3-61021
dimethylstilboestrol
phenol, 4,4'-((1e)-1,2-dimethyl-1,2-ethenediyl)bis-
4,4'-(1,2-dimethyl-1,2-ethenediyl)bis(phenol) (e)-
nsc 45946
phenol, 4,4'-(1,2-dimethyl-1,2-ethenediyl)bis-, (e)-
4,4'-stilbenediol, alpha,alpha'-dimethyl-, (e)-
CHEMBL269003
chebi:34717 ,
4-[(e)-3-(4-hydroxyphenyl)but-2-en-2-yl]phenol
bdbm50410510
phenol, 4,4'-(1,2-dimethyl-1,2-ethenediyl)bis-
13366-36-4
alpha,alpha'-dimethyl-4,4'-stilbenediol
4,4'-(1,2-dimethyl-1,2-ethenediyl)diphenol
4,4'-stilbenediol, alpha,alpha'-dimethyl
4,4'-stilbenediol, .alpha.,.alpha.'-dimethyl-, (e)-
.alpha.,.alpha.'-dimethyl-4,4'-stilbenediol
SCHEMBL125634
SCHEMBL125635
DTXSID2022468
Q27116241
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
stilbenoidAny olefinic compound characterised by a 1,2-diphenylethylene backbone.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Androgen receptorRattus norvegicus (Norway rat)IC50 (µMol)14.12540.00101.979414.1600AID255211
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID113030Uterotrophic effect in mice at 0 ug dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID113040Uterotrophic effect in mice at 1 ug dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID113060Uterotrophic effect in BD2F mice bearing transplantable hormone dependent MXT at 13.80 mg dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID113063Uterotrophic effect in BD2F mice bearing transplantable hormone dependent MXT at 2.76 mg dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID113048Uterotrophic effect in mice at 0 ug dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID117023Anti-uterotrophic effect in mice at 25 ug dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID121829Relative average tumor wet weight in treated compared to untreated mice at 2.76 mg dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID113056Uterotrophic effect in mice at 500 ug dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID69224Relative binding affinity ( relative to estradiol) to mouse estrogen receptor.1998Journal of medicinal chemistry, Jun-18, Volume: 41, Issue:13
Three-dimensional quantitative structure-activity relationship study of nonsteroidal estrogen receptor ligands using the comparative molecular field analysis/cross-validated r2-guided region selection approach.
AID255211Inhibitory concentration against recombinant rat androgen receptor expressed in Escherichia coli using [3H]methyltrienolone (R 1881)2005Journal of medicinal chemistry, Sep-08, Volume: 48, Issue:18
Impact of induced fit on ligand binding to the androgen receptor: a multidimensional QSAR study to predict endocrine-disrupting effects of environmental chemicals.
AID113054Uterotrophic effect in mice at 25 ug dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID121834Relative average tumor wet weight in treated compared to untreated mice at 8 mg dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID69704Relative binding affinity for sheep uterine estrogen receptor relative to estradiol as Ka(compound)/Ka(estradiol) x 1001980Journal of medicinal chemistry, Sep, Volume: 23, Issue:9
Estrogen receptor based imaging agents. 2. Synthesis and receptor binding affinity of side-chain halogenated hexestrol derivatives.
AID121827Relative average tumor wet weight in treated compared to untreated mice at 13.80 mg dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID113045Uterotrophic effect in mice at 100 ug dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID113055Uterotrophic effect in mice at 5 ug dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID124023Uterotrophic effect in BD2F mice bearing transplantable hormone dependent MXT at 8 mg dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID113052Uterotrophic effect in mice at 100 ug dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID113046Uterotrophic effect in mice at 1000 ug dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID113044Uterotrophic effect in mice at 10 ug dose1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
AID71119Relative Binding Affinity (RBA) for calf uterine estrogen receptor1986Journal of medicinal chemistry, Mar, Volume: 29, Issue:3
Influence of alkyl-chain fluorination on the action of mammary tumor inhibiting 2,3-bis(hydroxyphenyl)butanes and 2,3-bis(hydroxyphenyl)but-2-enes.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (80.00)18.7374
1990's1 (10.00)18.2507
2000's1 (10.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.68

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.68 (24.57)
Research Supply Index2.48 (2.92)
Research Growth Index4.17 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.68)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (9.09%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (90.91%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]