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
Molecular Formula C18H20O2
Molecular Weight 268.3502
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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
Late effects in the vaginal and cervical epithelia after injections of diethylstilbestrol into neonatal mice.
1975 Jan 1
Follow-up study of male and female offspring of DES-treated mothers a preliminary report.
1975 Jul
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
Sexual dimorphism in diethylstilbestrol-induced prolactin pituitary tumors in F344 rats.
2000 Aug
Assaying estrogenicity by quantitating the expression levels of endogenous estrogen-regulated genes.
2000 May
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
Cell-transforming activity and estrogenicity of bisphenol-A and 4 of its analogs in mammalian cells.
2001 Jul 1
4-Hydroxytamoxifen binds to and deactivates the estrogen-related receptor gamma.
2001 Jul 17
Estrogen and xenoestrogens upregulate the brain aromatase isoform (P450aromB) and perturb markers of early development in zebrafish (Danio rerio).
2001 Jun
Uterine adenocarcinoma in mice treated neonatally with genistein.
2001 Jun 1
Oestrogenic potencies of Zeranol, oestradiol, diethylstilboestrol, Bisphenol-A and genistein: implications for exposure assessment of potential endocrine disrupters.
2001 May
Assessment of oestrogenic potency of chemicals used as growth promoter by in-vitro methods.
2001 May
Concurrent primaries of vaginal clear cell adenocarcinoma and endometrial adenocarcinoma in a 39-year old woman with in utero diethylstilbestrol exposure.
2001 May-Jun
Cell response endpoints enhance sensitivity of the immature mouse uterotropic assay.
2001 May-Jun
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
Transcriptional regulation of the estrogen-inducible pS2 breast cancer marker gene by the ERR family of orphan nuclear receptors.
2001 Sep 15
Interaction of estrogen mimics, singly and in combination, with plasma sex steroid-binding proteins in rainbow trout (Oncorhynchus mykiss).
2002 Feb
Characterization of diethylstilbestrol-induced hypospadias in female mice.
2002 Jan 1
Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids.
2002 Jul
Cirrhosis with steatohepatitis following longterm stilboestrol treatment.
2003 Aug
Similarities and differences in uterine gene expression patterns caused by treatment with physiological and non-physiological estrogens.
2003 Dec
Estrogenic endocrine disruptive components interfere with calcium handling and differentiation of human trophoblast cells.
2003 Jul 1
Cytotoxic and xenoestrogenic effects via biotransformation of trans-anethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells.
2003 Jul 1
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
Prenatal exposure to estrogenic compounds alters the expression pattern of platelet-derived growth factor receptors alpha and beta in neonatal rat testis: identification of gonocytes as targets of estrogen exposure.
2003 Mar
Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals.
2003 Mar
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
Sulfonation of environmental estrogens by zebrafish cytosolic sulfotransferases.
2003 Sep 12
Neonatal estrogenization leads to increased expression of cellular retinol binding protein 2 in the mouse reproductive tract.
2004 Apr
Identification of estrogen-responsive genes by complementary deoxyribonucleic acid microarray and characterization of a novel early estrogen-induced gene: EEIG1.
2004 Feb
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
Diethylstilbestrol induces fish oocyte maturation.
2004 Mar 9
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10
JP4527401B2
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37
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15
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101
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5
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JPH04358132A
5
JPH04358133A
5
JPH06345625A
5
JPH08283707A
5
JPH08283708A
5
JPH08337557A
5
JPH09275998A
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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
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:35:47 GMT 2023
Edited
by admin
on Fri Dec 15 16:35:47 GMT 2023
Record UNII
731DCA35BT
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
ESTROGEN RECEPTOR
TARGET -> INHIBITOR
Binding Assay
IC50
Related Record Type Details
Structure of DIETHYLSTILBESTROL MONOGLUCURONIDE
METABOLITE -> PARENT
Related Record Type Details
Structure of DIETHYLSTILBESTROL
ACTIVE MOIETY
NIH
NCATS
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DISCLAIMER
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