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

Details

Stereochemistry ACHIRAL
Molecular Formula C18H20O2
Molecular Weight 268.3502
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DIETHYLSTILBESTROL

SMILES

CC\C(C1=CC=C(O)C=C1)=C(\CC)C2=CC=C(O)C=C2

InChI

InChIKey=RGLYKWWBQGJZGM-ISLYRVAYSA-N
InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: http://www.accessdata.fda.gov/drugsatfda_docs/nda/pre96/083003.pdf | https://en.wikipedia.org/wiki/Diethylstilbestrol | http://monographs.iarc.fr/ENG/Monographs/vol100A/mono100A-16.pdf

Diethylstilbestrol is a synthetic non-steroidal estrogen. It is used in the treatment of menopausal and postmenopausal disorders, prostate cancer and in the prevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery. Diethylstilbestrol is a very potent full agonist of the estrogen receptors. At the cellular level, estrogens increase the synthesis of DNA, RNA, and various proteins in target tissues. Pituitary mass is also increased. Estrogens reduce the release of gonadotropin-releasing hormone from the hypothalamus, leading to a reduction in release of follicle-stimulating hormone and luteinizing hormone from the pituitary. Adverse effects are: breast pain or tenderness, enlargement of breasts, gynecomastia, peripheral edema and others. Estrogens may interfere with the effects of bromocriptine. Dosage adjustment may be needed. Concurrent use with estrogens may alter the metabolism and protein binding of the glucocorticoids, leading to decreased clearance, increased elimination half-life, and increased therapeutic and toxic effects of the glucocorticoids.

Originator

Dodds E.C. et al.
5
Sources: DOI: 10.1016/0305-7372(84)90049-5https://www.nature.com/articles/141247b0
Curator's Comment: Fosfestrol was developed in the research laboratories of Asta-Werke and introduced in 1952 for the therapy of metastasizing prostatic carcinoma under the name of Honvan.

Approval Year

1941
158
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 0.18 nM [EC50]
Agonist
2678
 0.06 nM [EC50]
Inverse Agonist
80
 10.0 µM [EC50]
Inverse Agonist
80
 700.0 nM [EC50]
Inverse Agonist
80
 700.0 nM [EC50]
estrogen receptor 1
5
Target ID: P03372
Gene Symbol: ESR1
Agonist
2678
Inverse Agonist
80
 1.0 µM [IC50]
Inverse Agonist
80
 1.0 µM [IC50]
Inverse Agonist
80
 1.0 µM [IC50]
estrogen receptor 2 (ER beta)
5
Target ID: Q92731
Gene Symbol: ESR2
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Stilphostrol

Approved Use

Unknown

Launch Date

1981
Primary
Approved
8429
STILBESTROL

Approved Use

Used in the treatment of prostate cancer.

Launch Date

1973
Preventing
Approved
8429
STILBESTROL

Approved Use

Prevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery.

Launch Date

1973
Primary
Approved
8429
STILBESTROL

Approved Use

It is used for the treatment of senile (atrophic) vaginitis.

Launch Date

1973
Primary
Approved
8429
STILBESTROL

Approved Use

It is used for the treatment of vulvar dystrophy.

Launch Date

1973
Primary
Approved
8429
STILBESTROL

Approved Use

Other therapeutic use of diethylstilbestrol was post menopause syndrome.

Launch Date

1973
Primary
Approved
8429
STILBESTROL

Approved Use

Drug is indicated for replacement therapy of estrogen deficiency associated with amenorrhea.

Launch Date

1973
Primary
Approved
8429
STILBESTROL

Approved Use

Drug is indicated for replacement therapy of estrogen deficiency associated with female hypogonadism.

Launch Date

1973
Preventing
Approved
8429
STILBESTROL

Approved Use

Drug is indicated for the prevention of osteoporosis.

Launch Date

1973
Doses

Doses

DosePopulationAdverse events​
1104 mg 1 times / day multiple, intravenous
Recommended
Dose: 1104 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 1104 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12496896/
unhealthy, 56-87
n = 17
Health Status: unhealthy
Condition: prostate cancer
Age Group: 56-87
Sex: M
Population Size: 17
Sources:
https://pubmed.ncbi.nlm.nih.gov/12496896/
Disc. AE: Vomiting...
AEs leading to
discontinuation/dose reduction:
Vomiting (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12496896/
600 mg 1 times / day multiple, oral
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10526944/
unhealthy, 59
n = 1
Health Status: unhealthy
Condition: prostate cancer
Age Group: 59
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/10526944/
Disc. AE: Secondary adrenocortical insufficiency...
AEs leading to
discontinuation/dose reduction:
Secondary adrenocortical insufficiency
Sources:
https://pubmed.ncbi.nlm.nih.gov/10526944/
120 mg 3 times / day multiple, oral
Recommended
Dose: 120 mg, 3 times / day
Route: oral
Route: multiple
Dose: 120 mg, 3 times / day
Sources:
https://www.ijmpo.org/article.asp?issn=0971-5851;year=2019;volume=40;issue=1;spage=79;epage=84;aulast=Kalaiyarasi
unhealthy, 65
n = 47
Health Status: unhealthy
Condition: prostate cancer
Age Group: 65
Sex: M
Population Size: 47
Sources:
https://www.ijmpo.org/article.asp?issn=0971-5851;year=2019;volume=40;issue=1;spage=79;epage=84;aulast=Kalaiyarasi
Disc. AE: Toxic reaction (NOS), Toxic reaction (NOS)...
AEs leading to
discontinuation/dose reduction:
Toxic reaction (NOS) (grade 2, 3 patients)
Toxic reaction (NOS) (grade 3, 2 patients)
Sources:
https://www.ijmpo.org/article.asp?issn=0971-5851;year=2019;volume=40;issue=1;spage=79;epage=84;aulast=Kalaiyarasi
5.7 g 1 times / day multiple, intravenous
MTD
Dose: 5.7 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.7 g, 1 times / day
Co-administed with::
SALICYLIC ACID(200 mg; 1/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
unhealthy, 68
n = 21
Health Status: unhealthy
Condition: prostate cancer
Age Group: 68
Sex: M
Population Size: 21
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
DLT: Nausea and vomiting, Nausea and vomiting...
Dose limiting toxicities:
Nausea and vomiting (grade 1, 13 patients)
Nausea and vomiting (grade 2, 4 patients)
Weight gain (2 patients)
Edema (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
unhealthy, 70
n = 38
Health Status: unhealthy
Condition: prostate cancer
Age Group: 70
Sex: M
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
Other AEs: Hypertension, Gynecomastia...
Other AEs:
Hypertension (5%)
Gynecomastia (38%)
Peripheral edema (32%)
Gastrointestinal discomfort (19%)
Deep vein thrombosis (8%)
Skin rash (5%)
Transaminases increased (2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
1104 mg 1 times / day multiple, intravenous
Dose: 1104 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 1104 mg, 1 times / day
Co-administed with::
MEPERIDINE(75 mg; i.m; 1/day)
PROCHLORPERAZINE(12.5 mg; i.m; 1/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9607886/
unhealthy, 74
n = 17
Health Status: unhealthy
Condition: prostate cancer
Age Group: 74
Sex: M
Population Size: 17
Sources:
https://pubmed.ncbi.nlm.nih.gov/9607886/
Other AEs: Nausea, Bone pain...
Other AEs:
Nausea (17 patients)
Bone pain (17 patients)
Perineal pain (1 patient)
Deep vein thrombosis (4 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9607886/
4 g 1 times / day multiple, intravenous
RP2D
Dose: 4 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 4 g, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
unhealthy
Health Status: unhealthy
Condition: prostate cancer
Sex: M
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
AEs

AEs

AESignificanceDosePopulation
Vomiting 1 patient
Disc. AE
1104 mg 1 times / day multiple, intravenous
Recommended
Dose: 1104 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 1104 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12496896/
unhealthy, 56-87
n = 17
Health Status: unhealthy
Condition: prostate cancer
Age Group: 56-87
Sex: M
Population Size: 17
Sources:
https://pubmed.ncbi.nlm.nih.gov/12496896/
Secondary adrenocortical insufficiency Disc. AE
600 mg 1 times / day multiple, oral
Dose: 600 mg, 1 times / day
Route: oral
Route: multiple
Dose: 600 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10526944/
unhealthy, 59
n = 1
Health Status: unhealthy
Condition: prostate cancer
Age Group: 59
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/10526944/
Toxic reaction (NOS) grade 2, 3 patients
Disc. AE
120 mg 3 times / day multiple, oral
Recommended
Dose: 120 mg, 3 times / day
Route: oral
Route: multiple
Dose: 120 mg, 3 times / day
Sources:
https://www.ijmpo.org/article.asp?issn=0971-5851;year=2019;volume=40;issue=1;spage=79;epage=84;aulast=Kalaiyarasi
unhealthy, 65
n = 47
Health Status: unhealthy
Condition: prostate cancer
Age Group: 65
Sex: M
Population Size: 47
Sources:
https://www.ijmpo.org/article.asp?issn=0971-5851;year=2019;volume=40;issue=1;spage=79;epage=84;aulast=Kalaiyarasi
Toxic reaction (NOS) grade 3, 2 patients
Disc. AE
120 mg 3 times / day multiple, oral
Recommended
Dose: 120 mg, 3 times / day
Route: oral
Route: multiple
Dose: 120 mg, 3 times / day
Sources:
https://www.ijmpo.org/article.asp?issn=0971-5851;year=2019;volume=40;issue=1;spage=79;epage=84;aulast=Kalaiyarasi
unhealthy, 65
n = 47
Health Status: unhealthy
Condition: prostate cancer
Age Group: 65
Sex: M
Population Size: 47
Sources:
https://www.ijmpo.org/article.asp?issn=0971-5851;year=2019;volume=40;issue=1;spage=79;epage=84;aulast=Kalaiyarasi
Edema 2 patients
DLT
5.7 g 1 times / day multiple, intravenous
MTD
Dose: 5.7 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.7 g, 1 times / day
Co-administed with::
SALICYLIC ACID(200 mg; 1/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
unhealthy, 68
n = 21
Health Status: unhealthy
Condition: prostate cancer
Age Group: 68
Sex: M
Population Size: 21
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
Weight gain 2 patients
DLT
5.7 g 1 times / day multiple, intravenous
MTD
Dose: 5.7 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.7 g, 1 times / day
Co-administed with::
SALICYLIC ACID(200 mg; 1/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
unhealthy, 68
n = 21
Health Status: unhealthy
Condition: prostate cancer
Age Group: 68
Sex: M
Population Size: 21
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
Nausea and vomiting grade 1, 13 patients
DLT
5.7 g 1 times / day multiple, intravenous
MTD
Dose: 5.7 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.7 g, 1 times / day
Co-administed with::
SALICYLIC ACID(200 mg; 1/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
unhealthy, 68
n = 21
Health Status: unhealthy
Condition: prostate cancer
Age Group: 68
Sex: M
Population Size: 21
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
Nausea and vomiting grade 2, 4 patients
DLT
5.7 g 1 times / day multiple, intravenous
MTD
Dose: 5.7 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 5.7 g, 1 times / day
Co-administed with::
SALICYLIC ACID(200 mg; 1/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
unhealthy, 68
n = 21
Health Status: unhealthy
Condition: prostate cancer
Age Group: 68
Sex: M
Population Size: 21
Sources:
https://pubmed.ncbi.nlm.nih.gov/7508621/
Gastrointestinal discomfort 19%
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
unhealthy, 70
n = 38
Health Status: unhealthy
Condition: prostate cancer
Age Group: 70
Sex: M
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
Transaminases increased 2%
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
unhealthy, 70
n = 38
Health Status: unhealthy
Condition: prostate cancer
Age Group: 70
Sex: M
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
Peripheral edema 32%
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
unhealthy, 70
n = 38
Health Status: unhealthy
Condition: prostate cancer
Age Group: 70
Sex: M
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
Gynecomastia 38%
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
unhealthy, 70
n = 38
Health Status: unhealthy
Condition: prostate cancer
Age Group: 70
Sex: M
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
Hypertension 5%
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
unhealthy, 70
n = 38
Health Status: unhealthy
Condition: prostate cancer
Age Group: 70
Sex: M
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
Skin rash 5%
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
unhealthy, 70
n = 38
Health Status: unhealthy
Condition: prostate cancer
Age Group: 70
Sex: M
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
Deep vein thrombosis 8%
100 mg 3 times / day multiple, oral
Recommended
Dose: 100 mg, 3 times / day
Route: oral
Route: multiple
Dose: 100 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
unhealthy, 70
n = 38
Health Status: unhealthy
Condition: prostate cancer
Age Group: 70
Sex: M
Population Size: 38
Sources:
https://pubmed.ncbi.nlm.nih.gov/10761752/
Perineal pain 1 patient
1104 mg 1 times / day multiple, intravenous
Dose: 1104 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 1104 mg, 1 times / day
Co-administed with::
MEPERIDINE(75 mg; i.m; 1/day)
PROCHLORPERAZINE(12.5 mg; i.m; 1/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9607886/
unhealthy, 74
n = 17
Health Status: unhealthy
Condition: prostate cancer
Age Group: 74
Sex: M
Population Size: 17
Sources:
https://pubmed.ncbi.nlm.nih.gov/9607886/
Bone pain 17 patients
1104 mg 1 times / day multiple, intravenous
Dose: 1104 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 1104 mg, 1 times / day
Co-administed with::
MEPERIDINE(75 mg; i.m; 1/day)
PROCHLORPERAZINE(12.5 mg; i.m; 1/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9607886/
unhealthy, 74
n = 17
Health Status: unhealthy
Condition: prostate cancer
Age Group: 74
Sex: M
Population Size: 17
Sources:
https://pubmed.ncbi.nlm.nih.gov/9607886/
Nausea 17 patients
1104 mg 1 times / day multiple, intravenous
Dose: 1104 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 1104 mg, 1 times / day
Co-administed with::
MEPERIDINE(75 mg; i.m; 1/day)
PROCHLORPERAZINE(12.5 mg; i.m; 1/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9607886/
unhealthy, 74
n = 17
Health Status: unhealthy
Condition: prostate cancer
Age Group: 74
Sex: M
Population Size: 17
Sources:
https://pubmed.ncbi.nlm.nih.gov/9607886/
Deep vein thrombosis 4 patients
1104 mg 1 times / day multiple, intravenous
Dose: 1104 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 1104 mg, 1 times / day
Co-administed with::
MEPERIDINE(75 mg; i.m; 1/day)
PROCHLORPERAZINE(12.5 mg; i.m; 1/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9607886/
unhealthy, 74
n = 17
Health Status: unhealthy
Condition: prostate cancer
Age Group: 74
Sex: M
Population Size: 17
Sources:
https://pubmed.ncbi.nlm.nih.gov/9607886/
Sourcing

Sourcing

Vendor/AggregatorIDURL
A2Z Chemical
AZM13788
ABI Chem
AC1MHWYU
Aurora Fine Chemicals LLC
K16.450.167
http://online.aurorafinechemicals.com/info?ID=K16.450.167
BLD Pharm
BD131559
http://www.bldpharm.com/products/4719-75-9.html
BOC Sciences
4719-75-9
https://www.bocsci.com/tetrasodium-fosfestrol-cas-4719-75-9-item-15065.html
Changzhou Highassay Chemical Co., Ltd
my_sub1996
ChemMol
99096292
http://www.chemmol.com/chemmol/99096292.html
Glentham Life Sciences
GP2439
http://www.glentham.com/products/product/GP2439/
Hairui
HR110840
http://www.hairuichem.com/en/product/23519-26-8.html
NovoSeek
3034148
PubChem
3034148
https://pubchem.ncbi.nlm.nih.gov/compound/3034148
iChemical
EBD43877
http://www.ichemical.com/chemicals/cas-4719-75-9
PubMed

PubMed

TitleDatePubMed
Serum lipid levels and thromboembolic complications during estrogen therapy of prostatic cancer.
1975
Squamous neoplasia of vagina related to DES syndrome.
1975 May
Induction of urogenital anomalies and some tumors in the progeny of mice receiving diethylstilbestrol during pregnancy.
1977 Apr
Effects of estrogenic agents on chitobiase activity in the epidermis and hepatopancreas of the fiddler crab, Uca pugilator.
1999 Feb
Rapid inhibition of rat brain mitochondrial proton F0F1-ATPase activity by estrogens: comparison with Na+, K+ -ATPase of porcine cortex.
1999 Feb 26
Myopia in diethylstilboestrol exposed amblyopic subjects.
1999 Jan
Low-dose bioactivity of xenoestrogens in animals: fetal exposure to low doses of methoxychlor and other xenoestrogens increases adult prostate size in mice.
1999 Jan-Mar
Transplacental administration of diethylstilbestrol (DES) causes lesions in female reproductive organs of Donryu rats, including endometrial neoplasia.
1999 Jul 1
Estrogen receptor activation via activation function 2 predicts agonism of xenoestrogens in normal and neoplastic cells of the uterine myometrium.
1999 Jul 1
The role of estrogen receptor, androgen receptor and growth factors in diethylstilbestrol-induced programming of prostate differentiation.
2000 Aug
Sexual dimorphism in diethylstilbestrol-induced prolactin pituitary tumors in F344 rats.
2000 Aug
Exposure of newborn male and female rats to environmental estrogens: delayed and sustained hyperprolactinemia and alterations in estrogen receptor expression.
2000 Dec
Differential estrogen receptor binding of estrogenic substances: a species comparison.
2000 Nov 15
Estrogen inhibition of cystic fibrosis transmembrane conductance regulator-mediated chloride secretion.
2000 Oct
Activation of a uterine insulin-like growth factor I signaling pathway by clinical and environmental estrogens: requirement of estrogen receptor-alpha.
2000 Sep
Diethylstilbestrol regulates trophoblast stem cell differentiation as a ligand of orphan nuclear receptor ERR beta.
2001 Apr 1
The role of diethylstilbestrol in the treatment of prostate cancer.
2001 Aug
Uterine adenocarcinoma in mice treated neonatally with genistein.
2001 Jun 1
Metabolism of bisphenol A in isolated rat hepatocytes and oestrogenic activity of a hydroxylated metabolite in MCF-7 human breast cancer cells.
2001 Mar
Effects of prenatal exposure to low doses of diethylstilbestrol, o,p'DDT, and methoxychlor on postnatal growth and neurobehavioral development in male and female mice.
2001 Sep
Comparison of an array of in vitro assays for the assessment of the estrogenic potential of natural and synthetic estrogens, phytoestrogens and xenoestrogens.
2001 Sep 14
Transcriptional regulation of the estrogen-inducible pS2 breast cancer marker gene by the ERR family of orphan nuclear receptors.
2001 Sep 15
Uterine responsiveness to estradiol and DNA methylation are altered by fetal exposure to diethylstilbestrol and methoxychlor in CD-1 mice: effects of low versus high doses.
2002 Aug 15
Improvement of a sensitive enzyme-linked immunosorbent assay for screening estrogen receptor binding activity.
2002 Dec
Increases in mouse uterine heat shock protein levels are a sensitive and specific response to uterotrophic agents.
2002 Dec
Induction of reproductive tract developmental abnormalities in the male rat by lowering androgen production or action in combination with a low dose of diethylstilbestrol: evidence for importance of the androgen-estrogen balance.
2002 Dec
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.
2002 Jul
Estrogen receptor binding assay of chemicals with a surface plasmon resonance biosensor.
2002 May
Responsiveness of endometrial genes Connexin26, Connexin43, C3 and clusterin to primary estrogen, selective estrogen receptor modulators, phyto- and xenoestrogens.
2002 Oct
Modulation of the onset of postnatal development of H(+)-ATPase-rich cells by steroid hormones in rat epididymis.
2002 Oct
Effect of diethylstilbestrol on polyamine metabolism in hamster epididymis.
2003 Dec
Diethylstilbestrol induces rat spermatogenic cell apoptosis in vivo through increased expression of spermatogenic cell Fas/FasL system.
2003 Feb 21
Oxidative DNA damage induced by toluene is involved in its male reproductive toxicity.
2003 Jan
Long-lasting effects of lindane on mouse spermatogenesis induced by in utero exposure.
2003 Jan-Feb
Update on cryptorchidism: endocrine, environmental and therapeutic aspects.
2003 Jun
Differential expression of c-fos and c-myc protooncogenes by estrogens, xenobiotics and other growth-stimulatory agents in primary rat hepatocytes.
2003 Mar
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.
2003 Oct
Neonatal diethylstilbestrol exposure induces persistent elevation of c-fos expression and hypomethylation in its exon-4 in mouse uterus.
2003 Oct
Autocrine/paracrine action of pituitary vasoactive intestinal peptide on lactotroph hyperplasia induced by estrogen.
2003 Oct
Combined effects of tumor promoters and serum on proliferin mRNA induction: a biomarker sensitive to saccharin, 2,3,7,8-TCDD, and other compounds at minimal concentrations promoting C3H/10T1/2 cell transformation.
2003 Oct 24
Induction of vitellogenin synthesis in an Atlantic salmon (Salmo salar) hepatocyte culture: a sensitive in vitro bioassay for the oestrogenic and anti-oestrogenic activity of chemicals.
2003 Sep-Oct
Neonatal estrogenization leads to increased expression of cellular retinol binding protein 2 in the mouse reproductive tract.
2004 Apr
Comparison of the Hershberger assay and androgen receptor binding assay of twelve chemicals.
2004 Feb 15
Dimerization modulates the activity of the orphan nuclear receptor ERRgamma.
2004 Feb 20
Long-term alteration of gene expression without morphological change in testis after neonatal exposure to genistein in mice: toxicogenomic analysis using cDNA microarray.
2004 Mar
Modulation of AhR-mediated CYP1A1 mRNA and EROD activities by 17beta-estradiol and dexamethasone in TCDD-induced H411E cells.
2004 Mar
Diethylstilbestrol induces fish oocyte maturation.
2004 Mar 9
Small nuclear RING finger protein expression during gonad development: regulation by gonadotropins and estrogen in the postnatal ovary.
2004 May
Abnormal morphology of the penis in male rats exposed neonatally to diethylstilbestrol is associated with altered profile of estrogen receptor-alpha protein, but not of androgen receptor protein: a developmental and immunocytochemical study.
2004 May
Upregulation of angiotensin II type 2 receptor expression in estrogen-induced pituitary hyperplasia.
2004 May
Patents

Patents

03989825
6
04055638
6
05030328
7
05811547
5
05962438
5
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9
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34
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414
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15
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87
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101
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33
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31
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5
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5
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5
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5
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5
JPH08283707A
5
JPH08283708A
5
JPH08337557A
5
JPH09275998A
5
JPH093014A
5
JPS59155337A
5
JPS60208905A
8
JPS6143101A
5
JPS6440412A
12

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Intravenous: Initial: 600-1,200 mg/day via slow injection for 5-10 days, then 300 mg/day for 10-20 days.
360-480 mg 3 times/day. Maintenance: 120-240 mg 3 times/day.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: There was exposed three prostatic carcinoma cell lines (LNCaP, DU 145, and PC-3), three non-prostatic neoplastic cell lines (KB: epidermoid carcinoma, EJ: Bladder carcinoma, Daudi: Burkitt lymphoma), and one non-transformed embryonic fibroblast line (MRC-5) to diethylstilbestrol (DES), DES monophosphate, and DES diphosphate (DESDP), at levels comparable to those occurring in patients’ sera during DESDP infusions. At concentrations of 1–20 µg/ml the drugs showed marked, dose-dependent cytotoxicity towards all cell lines under study.
1–20 µg/ml
Name Type Language
DIETHYLSTILBESTROL
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
Diethylstilbestrol [WHO-DD]
Common Name English
STILBETIN
Brand Name English
DIETHYLSTILBESTROL [ORANGE BOOK]
Common Name English
DIETHYLSTILBESTROL [IARC]
Common Name English
.ALPHA.,.ALPHA.'-DIETHYL-(E)-4,4'-STILBENEDIOL
Common Name English
STILBESTRO
Brand Name English
PHENOL 4,4'-(1,2-DIETHYL-1,2-ETHENEDIYL)BIS-, (E)-
Common Name English
NSC-3070
Code English
DIETHYLSTILBESTROL [MI]
Common Name English
STILBESTROL
Brand Name English
DIETHYLSTILBESTROL [USP-RS]
Common Name English
DIETHYLSTILBESTROL [EP MONOGRAPH]
Common Name English
DIETHYLSTILBESTROL [MART.]
Common Name English
DIETHYLSTILBESTROL [HSDB]
Common Name English
diethylstilbestrol [INN]
Common Name English
DIETHYLSTILBESTROL [VANDF]
Common Name English
DIETHYLSTILBESTROL [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
WHO-VATC QG03CC05
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
WHO-VATC QL02AA01
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
CFR 21 CFR 530.41
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
NCI_THESAURUS C2182
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
IARC Diethylstilbestrol
WHO-ATC L02AA01
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
WHO-ATC G03CB02
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
WHO-VATC QG03CB02
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
WHO-ATC G03CC05
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
Code System Code Type Description
DRUG CENTRAL
875
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
SMS_ID
100000085041
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID3020465
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
HSDB
3060
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
FDA UNII
731DCA35BT
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
CAS
56-53-1
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
NSC
3070
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
ChEMBL
CHEMBL411
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
INN
388
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
PUBCHEM
448537
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
MERCK INDEX
m4418
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
DIETHYLSTILBESTROL
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-278-5
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
RS_ITEM_NUM
1195001
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
EVMPD
SUB07112MIG
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
NCI_THESAURUS
C433
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
CHEBI
41922
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
DAILYMED
731DCA35BT
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
MESH
D004054
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
RXCUI
3390
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB00255
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
IUPHAR
2801
Created by admin on Fri Dec 15 16:35:47 GMT 2023 , Edited by admin on Fri Dec 15 16:35:47 GMT 2023
PRIMARY
NIH
NCATS
PRIVACY ACT
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