DGIdb - DIETHYLSTILBESTROL Drug Record

DIETHYLSTILBESTROL chembl:CHEMBL411 Antineoplastic

Alternate Names:

STILBESTROFORM
ESTROGENINE
SYNESTRIN
STILBOESTROL
SYNTHESTRIN
TAMPOVAGAN
CYREN A
DIETHYLSTILBESTROL
NEW-ESTRANOL 1
PALESTROL
STILBETIN
APSTIL
ESTROMENIN
NSC-3070
ESTROBENE
STILBESTROL
STILBOESTEROL
FONATOL
DISTILBENE
TRANS-DIETHYLSTILBOESTEROL
(E)-3,4-BIS(4-HYDROXYPHENYL)-3-HEXENE
4,4'-DIHYDROXY-ALPHA,BETA-DIETHYLSTILBENE
(E)-4,4'-(1,2-DIETHYL-1,2-ETHENEDIYL)BISPHENOL
TRANS-DIETHYLSTILBESTEROL
Α,Α'-DIETHYL-(E)-4,4'-STILBENEDIOL
ALPHA,ALPHA'-DIETHYL-(E)-4,4'-STILBENEDIOL
TRANS-DIETHYLSTILBESTROL
TRANS-4,4'-(1,2-DIETHYL-1,2-ETHENEDIYL)BISPHENOL
4,4'-DIHYDROXY-Α,Β-DIETHYLSTILBENE
DES
DIETHYLSTILBESTROLUM
DIETILESTILBESTROL
chembl:CHEMBL411
chemidplus:56-53-1
pubchem.compound:448537
drugbank:00255
rxcui:3390

Drug Info:

Drug Class	hormone replacement agents
Year of Approval	approved before 1982
FDA Approval	Approved before 1982
Drug Class	small molecule
Drug Indications	Hormone Replacement Agents

(5 More Sources)

Publications:

Hodnik Ž et al., 2015, Diethylstilbestrol-scaffold-based pregnane X receptor modulators., Eur J Med Chem
Kretschmer XC et al., 2005, CAR and PXR: xenosensors of endocrine disrupters?, Chem Biol Interact
Visser et al., 1998, Effect of prenatal exposure to diethylstilbestrol on Müllerian duct development in fetal male mice., Endocrinology
Wang et al., 1990, Lectin bindings and diethylstilbestrol effects on the recognition of mullerian inhibiting substance (MIS) on chick mullerian ducts by MIS-antiserum., Histochemistry
Salleh et al., 2004, Gene expression profiling of p53(+/-) knockout and wild-type mice following diethylstilbestrol administration., IUBMB Life
Berman et al., 2000, The Protein Data Bank., Nucleic Acids Res.
Greschik et al., 2004, Structural basis for the deactivation of the estrogen-related receptor gamma by diethylstilbestrol or 4-hydroxytamoxifen and determinants of selectivity., J. Biol. Chem.
Nam et al., 2003, Simulation of the different biological activities of diethylstilbestrol (DES) on estrogen receptor alpha and estrogen-related receptor gamma., Biopolymers
Tremblay et al., 2001, Diethylstilbestrol regulates trophoblast stem cell differentiation as a ligand of orphan nuclear receptor ERR beta., Genes Dev.
Kwok et al., 2010, Measuring binding kinetics of ligands with tethered receptors by fluorescence polarization and total internal reflection fluorescence., Anal. Chem.
Hart et al., 2007, Estrogen mobilizes a subset of estrogen receptor-alpha-immunoreactive vesicles in inhibitory presynaptic boutons in hippocampal CA1., J. Neurosci.
Muñoz et al., Association with litter size of new polymorphisms on ESR1 and ESR2 genes in a Chinese-European pig line., Genet. Sel. Evol.
Baron et al., 2007, Estrogen receptor alpha and the activating protein-1 complex cooperate during insulin-like growth factor-I-induced transcriptional activation of the pS2/TFF1 gene., J. Biol. Chem.
Chen et al., 2002, TTD: Therapeutic Target Database., Nucleic Acids Res.
Dixon et al., 2007, Renoprotective effects of a selective estrogen receptor modulator, raloxifene, in an animal model of diabetic nephropathy., Am. J. Nephrol.
Bains et al., 2007, Neuroprotection by estrogen against MPP+-induced dopamine neuron death is mediated by ERalpha in primary cultures of mouse mesencephalon., Exp. Neurol.
Noubani et al., 2000, B-type natriuretic peptide receptor expression and activity are hormonally regulated in rat ovarian cells., Endocrinology
Miller et al., 1998, Fetal exposure to DES results in de-regulation of Wnt7a during uterine morphogenesis., Nat. Genet.
Tamura H et al., 2006, Structural basis for androgen receptor agonists and antagonists: interaction of SPEED 98-listed chemicals and related compounds with the androgen receptor based on an in vitro reporter gene assay and 3D-QSAR., Bioorg Med Chem
Ramos et al., 2007, Diethylstilbestrol alters the population dynamic of neural precursor cells in the neonatal male rat dentate gyrus., Brain Res. Bull.
Sakatis MZ et al., 2012, Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds., Chem Res Toxicol
Wu et al., 2006, [Effect of environmental contaminants on DNA methyltransferase activity of mouse preimplantation embryos]., Wei Sheng Yan Jiu
Wang et al., 2004, Prenatal estrogen exposure differentially affects estrogen receptor-associated proteins in rat testis gonocytes., Biol. Reprod.
Shepel et al., 1990, Restriction fragment length polymorphisms in the rat N-ras and retinoblastoma genes: their identification and characterization., Oncogene
Kendall et al., 1992, The effects of diethylstilbestrol, tamoxifen, and toremifene on estrogen-inducible hepatic proteins and estrogen receptor proteins in female rats., Toxicol. Appl. Pharmacol.
Ghibaudi et al., 2000, Can estrogenic radicals, generated by lactoperoxidase, be involved in the molecular mechanism of breast carcinogenesis?, Redox Rep.
Li et al., 1983, Effect of steroid hormone treatment on aryl hydrocarbon hydroxylase activity in the Syrian hamster kidney., Biochem. Pharmacol.
Miyagawa et al., 2004, Estrogen-independent activation of erbBs signaling and estrogen receptor alpha in the mouse vagina exposed neonatally to diethylstilbestrol., Oncogene

DIETHYLSTILBESTROL ESRRB

Interaction Score: 6.4

Interaction Types & Directionality:

antagonist (inhibitory)

Interaction Info:

PMIDs:
26408814 11297507

Sources:
DTC
DIETHYLSTILBESTROL ESRRG

Interaction Score: 5.33

Interaction Types & Directionality:

agonist (activating)

antagonist (inhibitory)

Interaction Info:

PMIDs:
10592235 15161930 12579585 11297507

Sources:
NCI
DIETHYLSTILBESTROL WNT7A

Interaction Score: 4.26

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
9806537

Sources:
NCI
DIETHYLSTILBESTROL AMH

Interaction Score: 3.2

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
9751506 2286533

Sources:
NCI
DIETHYLSTILBESTROL LPO

Interaction Score: 1.42

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
10994878

Sources:
NCI
DIETHYLSTILBESTROL PTGES3

Interaction Score: 1.42

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
15229138

Sources:
NCI
DIETHYLSTILBESTROL NPPC

Interaction Score: 0.43

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
10650935

Sources:
NCI
DIETHYLSTILBESTROL CP

Interaction Score: 0.3

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
1533964

Sources:
NCI
DIETHYLSTILBESTROL E2F1

Interaction Score: 0.27

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
15545218

Sources:
NCI
DIETHYLSTILBESTROL DNMT1

Interaction Score: 0.16

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
16598927

Sources:
NCI
DIETHYLSTILBESTROL ESR1

Interaction Score: 0.14

Interaction Types & Directionality:

agonist (activating)

Interaction Info:

Novel drug target Established target

Trial Name -

Direct Interaction yes

PMIDs:
20387803 17314305 17306201 17317669 11752352 17308373 17320868 26408814

Sources:
DTC TdgClinicalTrial ChemblInteractions TEND TTD
DIETHYLSTILBESTROL HRAS

Interaction Score: 0.13

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
1980008

Sources:
NCI
DIETHYLSTILBESTROL MYC

Interaction Score: 0.11

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
15545218

Sources:
NCI
DIETHYLSTILBESTROL BCL2

Interaction Score: 0.1

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
15545218

Sources:
NCI
DIETHYLSTILBESTROL NR1I2

Interaction Score: 0.08

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
26408814 16054614

Sources:
DTC PharmGKB
DIETHYLSTILBESTROL SLC5A7

Interaction Score: 0.08

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
None found

Sources:
DTC
DIETHYLSTILBESTROL BDNF

Interaction Score: 0.07

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
17292805

Sources:
NCI
DIETHYLSTILBESTROL NR1H4

Interaction Score: 0.03

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
None found

Sources:
DTC
DIETHYLSTILBESTROL ERBB2

Interaction Score: 0.03

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
14647453

Sources:
NCI
DIETHYLSTILBESTROL RORC

Interaction Score: 0.02

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
None found

Sources:
DTC
DIETHYLSTILBESTROL TP53

Interaction Score: 0.01

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
15545218

Sources:
NCI
DIETHYLSTILBESTROL CYP2C9

Interaction Score: 0.01

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
22931300

Sources:
DTC
DIETHYLSTILBESTROL CYP2C19

Interaction Score: 0.01

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
22931300

Sources:
DTC
DIETHYLSTILBESTROL CYP1A2

Interaction Score: 0.01

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
6626258

Sources:
NCI
DIETHYLSTILBESTROL CYP2D6

Interaction Score: 0.01

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
22931300

Sources:
DTC
DIETHYLSTILBESTROL AR

Interaction Score: 0.0

Interaction Types & Directionality:

antagonist (inhibitory)

Interaction Info:

PMIDs:
16876421

Sources:
DTC
DIETHYLSTILBESTROL CYP3A4

Interaction Score: 0.0

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
22931300

Sources:
DTC
DIETHYLSTILBESTROL GMNN

Interaction Score: 0.0

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
None found

Sources:
DTC
DIETHYLSTILBESTROL NFE2L2

Interaction Score: 0.0

Interaction Types & Directionality:

n/a

Interaction Info:

PMIDs:
None found

Sources:
DTC

TEND: DIETHYLSTILBESTROL
- Version: 01-August-2011
Alternate Names:

DIETHYLSTILBESTROL Primary Drug Name

Drug Info:

Year of Approval approved before 1982

Drug Class hormone replacement agents

Publications:
TdgClinicalTrial: DIETHYLSTILBESTROL
- Version: January-2014
Alternate Names:

Drug Info:

Drug Indications Hormone Replacement Agents

Drug Class small molecule

FDA Approval Approved before 1982

Publications:

DTC: DIETHYLSTILBESTROL

Version: 02-September-2020

Alternate Names:

CHEMBL411 ChEMBL Drug ID

Drug Info:

Publications:

Sakatis MZ et al., 2012, Preclinical strategy to reduce clinical hepatotoxicity using in vitro bioactivation data for >200 compounds., Chem Res Toxicol

Hodnik Ž et al., 2015, Diethylstilbestrol-scaffold-based pregnane X receptor modulators., Eur J Med Chem

NCI: DIETHYLSTILBESTROL

Version: 14-September-2017

Alternate Names:

C433 NCI drug code

Drug Info:

Publications:

Wang et al., 1990, Lectin bindings and diethylstilbestrol effects on the recognition of mullerian inhibiting substance (MIS) on chick mullerian ducts by MIS-antiserum., Histochemistry

Shepel et al., 1990, Restriction fragment length polymorphisms in the rat N-ras and retinoblastoma genes: their identification and characterization., Oncogene

Wu et al., 2006, [Effect of environmental contaminants on DNA methyltransferase activity of mouse preimplantation embryos]., Wei Sheng Yan Jiu

NCI: DES

Version: 14-September-2017

Alternate Names:

C433 NCI drug code

Drug Info:

Publications:

Salleh et al., 2004, Gene expression profiling of p53(+/-) knockout and wild-type mice following diethylstilbestrol administration., IUBMB Life

Kendall et al., 1992, The effects of diethylstilbestrol, tamoxifen, and toremifene on estrogen-inducible hepatic proteins and estrogen receptor proteins in female rats., Toxicol. Appl. Pharmacol.

Ramos et al., 2007, Diethylstilbestrol alters the population dynamic of neural precursor cells in the neonatal male rat dentate gyrus., Brain Res. Bull.

TTD: Diethylstilbestrol
- Version: 2020.06.01
Alternate Names:

D0Y2NE TTD Drug ID

Drug Info:

Publications:
ChemblDrugs: chembl:CHEMBL411
- Version: ChEMBL_27
Alternate Names:

Drug Info:

Publications:
ChemblInteractions: CHEMBL411
- Version: chembl_23
Alternate Names:

Drug Info:

Publications:
PharmGKB: diethylstilbestrol
- Version: 18-August-2020
Alternate Names:

Drug Info:

Publications:

Novel drug target	Established target
Trial Name	-
Direct Interaction	yes

agonist (activating)
antagonist (inhibitory)

DIETHYLSTILBESTROL Drug Record

DIETHYLSTILBESTROL chembl:CHEMBL411 Antineoplastic

Alternate Names:

Drug Info:

Publications:

Interaction Types & Directionality: antagonist (inhibitory)

Interaction Info:

PMIDs: 26408814 11297507

Sources: DTC

Interaction Types & Directionality: agonist (activating) antagonist (inhibitory)

Interaction Info:

PMIDs: 10592235 15161930 12579585 11297507

Sources: NCI

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 9806537

Sources: NCI

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 9751506 2286533

Sources: NCI

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 10994878

Sources: NCI

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 15229138

Sources: NCI

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 10650935

Sources: NCI

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 1533964

Sources: NCI

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 15545218

Sources: NCI

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 16598927

Sources: NCI

Interaction Types & Directionality: agonist (activating)

Interaction Info: Novel drug target Established target Trial Name - Direct Interaction yes

PMIDs: 20387803 17314305 17306201 17317669 11752352 17308373 17320868 26408814

Sources: DTC TdgClinicalTrial ChemblInteractions TEND TTD

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 1980008

Sources: NCI

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 15545218

Sources: NCI

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 15545218

Sources: NCI

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 26408814 16054614

Sources: DTC PharmGKB

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: None found

Sources: DTC

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 17292805

Sources: NCI

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: None found

Sources: DTC

Interaction Types & Directionality: n/a

Interaction Info:

PMIDs: 14647453

Interaction Types & Directionality:

antagonist (inhibitory)

PMIDs:
26408814 11297507

Sources:
DTC

Interaction Types & Directionality:

agonist (activating)

antagonist (inhibitory)

PMIDs:
10592235 15161930 12579585 11297507

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
9806537

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
9751506 2286533

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
10994878

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
15229138

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
10650935

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
1533964

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
15545218

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
16598927

Sources:
NCI

Interaction Types & Directionality:

agonist (activating)

Interaction Info:

Novel drug target Established target

Trial Name -

Direct Interaction yes

PMIDs:
20387803 17314305 17306201 17317669 11752352 17308373 17320868 26408814

Sources:
DTC TdgClinicalTrial ChemblInteractions TEND TTD

Interaction Types & Directionality:

n/a

PMIDs:
1980008

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
15545218

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
15545218

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
26408814 16054614

Sources:
DTC PharmGKB

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
17292805

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
14647453

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
None found

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
15545218

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
22931300

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
22931300

Sources:
DTC

Interaction Types & Directionality:

n/a

PMIDs:
6626258

Sources:
NCI

Interaction Types & Directionality:

n/a

PMIDs:
22931300

Sources:
DTC

Interaction Types & Directionality:

antagonist (inhibitory)

PMIDs:
16876421

Sources:
DTC

Interaction Types & Directionality:

n/a