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

Details

Stereochemistry ACHIRAL
Molecular Formula C18H22O8P2
Molecular Weight 428.31
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FOSFESTROL

SMILES

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

InChI

InChIKey=NLORYLAYLIXTID-ISLYRVAYSA-N
InChI=1S/C18H22O8P2/c1-3-17(13-5-9-15(10-6-13)25-27(19,20)21)18(4-2)14-7-11-16(12-8-14)26-28(22,23)24/h5-12H,3-4H2,1-2H3,(H2,19,20,21)(H2,22,23,24)/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
Clear cell adenocarcinoma of the cervix and vagina. A clinicopathologic study of 21 cases with and without a history of maternal ingestion of estrogens.
1976 Feb
Induction of urogenital anomalies and some tumors in the progeny of mice receiving diethylstilbestrol during pregnancy.
1977 Apr
Effect of mesulergine on prolactin secretion and dopamine D2 receptors-adaptive changes in diethylstilbestrol-induced hyperplasia of the rat anterior pituitary.
1992 Mar
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
Activation of estrogen receptor alpha and ERbeta by 4-methylbenzylidene-camphor in human and rat cells: comparison with phyto- and xenoestrogens.
2003 Apr 30
Cirrhosis with steatohepatitis following longterm stilboestrol treatment.
2003 Aug
Effect of diethylstilbestrol on polyamine metabolism in hamster epididymis.
2003 Dec
Similarities and differences in uterine gene expression patterns caused by treatment with physiological and non-physiological estrogens.
2003 Dec
The inhibitory effects of flavonoids and antiestrogens on the Glut1 glucose transporter in human erythrocytes.
2003 Dec 15
The immune system of geriatric mice is modulated by estrogenic endocrine disruptors (diethylstilbestrol, alpha-zearalanol, and genistein): effects on interferon-gamma.
2003 Dec 15
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
Simulation of the different biological activities of diethylstilbestrol (DES) on estrogen receptor alpha and estrogen-related receptor gamma.
2003 Jan
Endocrine disrupting chemicals: interference of thyroid hormone binding to transthyretins and to thyroid hormone receptors.
2003 Jan 31
Long-lasting effects of lindane on mouse spermatogenesis induced by in utero exposure.
2003 Jan-Feb
In vitro modulation of prolactin mRNA by toxaphene and 3,3',4,4'-tetrachlorobiphenyl.
2003 Jul
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
Effects of endocrine disrupting compounds on the pathology and oestrogen receptor alpha and beta distribution in the uterus and cervix of ewe lambs.
2003 Nov
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
The effect of endocrine disrupting chemicals on thyroid hormone binding to Japanese quail transthyretin and thyroid hormone receptor.
2003 Oct 15
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
Limb reduction defects in the first generation and deafness in the second generation of intrauterine exposed fetuses to diethylstilbestrol.
2003 Oct-Dec
Sulfonation of environmental estrogens by zebrafish cytosolic sulfotransferases.
2003 Sep 12
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
Identification of estrogen-responsive genes by complementary deoxyribonucleic acid microarray and characterization of a novel early estrogen-induced gene: EEIG1.
2004 Feb
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
Age, sex and co-exposure to N-ethyl-N-nitrosourea influence mutations in the Alu repeat sequences in diethylstilbestrol-induced kidney tumors in Syrian hamsters.
2004 Jan
Toxicogenomic difference between diethylstilbestrol and 17beta-estradiol in mouse testicular gene expression by neonatal exposure.
2004 Jan
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

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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
FOSFESTROL
INN   MART.   MI   WHO-DD  
INN  
Official Name English
DIETHYLSTILBESTROL DIPHOSPHATE [VANDF]
Common Name English
FOSFESTROL [MART.]
Common Name English
FOSFESTROL [JAN]
Common Name English
fosfestrol [INN]
Common Name English
DIETHYLSTILBESTROL DIPHOSPHATE [ORANGE BOOK]
Common Name English
PHENOL, 4,4'-(1,2-DIETHYL-1,2-ETHENEDIYL)BIS-, BIS(DIHYDROGEN PHOSPHATE), (E)
Common Name English
.ALPHA.,.ALPHA.'-DIETHYL-(E)-4,4'-STILBENEDIOL BIS(DIHYDROGEN PHOSPHATE)
Common Name English
STILPHOSTROL
Brand Name English
DIETHYLSTILBESTROL DIPHOSPHATE
ORANGE BOOK   VANDF  
Systematic Name English
FOSFESTROL [MI]
Common Name English
Fosfestrol [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC L02AA04
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
NCI_THESAURUS C2182
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
WHO-VATC QL02AA04
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
Code System Code Type Description
SMS_ID
100000086880
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
DRUG CENTRAL
3248
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID3046906
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
DRUG BANK
DBSALT001389
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
MERCK INDEX
m5550
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
FOSFESTROL
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
FDA UNII
A0E0NMA80F
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
MESH
C004955
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
NCI_THESAURUS
C1105
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-328-8
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
RXCUI
25284
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY RxNorm
PUBCHEM
3032325
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200598
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
CAS
522-40-7
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
INN
1824
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
EVMPD
SUB07795MIG
Created by admin on Fri Dec 15 15:00:28 GMT 2023 , Edited by admin on Fri Dec 15 15:00:28 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of FOSFESTROL
SALT/SOLVATE (PARENT)
Structure of FOSFESTROL SODIUM
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
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