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

Details

Stereochemistry ACHIRAL
Molecular Formula C18H18O8P2.4Na
Molecular Weight 516.2373
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FOSFESTROL SODIUM

SMILES

[Na+].[Na+].[Na+].[Na+].CC\C(C1=CC=C(OP([O-])([O-])=O)C=C1)=C(\CC)C2=CC=C(OP([O-])([O-])=O)C=C2

InChI

InChIKey=XGZAXRQNRRXUMY-MJCKVQKWSA-J
InChI=1S/C18H22O8P2.4Na/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);;;;/q;4*+1/p-4/b18-17+;;;;

HIDE SMILES / InChI
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C18H18O8P2
Molecular Weight 424.2782
Charge -4
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
Serum lipid levels and thromboembolic complications during estrogen therapy of prostatic cancer.
1975
The Veterans' Administration Cooperative Urological Research Group studies of carcinoma of the prostate: a review.
1975 Jan-Feb
Endometrial carcinoma after cyclical oestrogen-progestogen therapy for Turner's syndrome.
1975 May
Induction of urogenital anomalies and some tumors in the progeny of mice receiving diethylstilbestrol during pregnancy.
1977 Apr
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
Sulfation of environmental estrogen-like chemicals by human cytosolic sulfotransferases.
2000 Jan 7
Pubertal development and reproductive functions of Crl:CD BR Sprague-Dawley rats exposed to bisphenol A during prenatal and postnatal development.
2000 Jun
Reproductive malformation of the male offspring following maternal exposure to estrogenic chemicals.
2000 Jun
Differential estrogen receptor binding of estrogenic substances: a species comparison.
2000 Nov 15
Differential effects of xenoestrogens on coactivator recruitment by estrogen receptor (ER) alpha and ERbeta.
2000 Nov 17
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
Estrogenic potency of benzophenone and its metabolites in juvenile female rats.
2001 Apr
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
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
Metabolism of bisphenol A in isolated rat hepatocytes and oestrogenic activity of a hydroxylated metabolite in MCF-7 human breast cancer cells.
2001 Mar
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
Modulation by estrogens and xenoestrogens of recombinant human neuronal nicotinic receptors.
2001 Nov 2
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
Characterization of diethylstilbestrol-induced hypospadias in female mice.
2002 Jan 1
Modulation of the onset of postnatal development of H(+)-ATPase-rich cells by steroid hormones in rat epididymis.
2002 Oct
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
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
Cytotoxic and xenoestrogenic effects via biotransformation of trans-anethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells.
2003 Jul 1
Differential expression of c-fos and c-myc protooncogenes by estrogens, xenobiotics and other growth-stimulatory agents in primary rat hepatocytes.
2003 Mar
Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals.
2003 Mar
Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor.
2003 Oct
The effect of endocrine disrupting chemicals on thyroid hormone binding to Japanese quail transthyretin and thyroid hormone receptor.
2003 Oct 15
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
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
Patents

Patents

03989825
6
04055638
6
05030328
7
05811547
5
05962438
5
JP1040412A
9
JP2000044435A
34
JP2000159733A
5
JP2001048900A
5
JP2002511777A
414
JP2002525268A
31
JP2003529540A
49
JP2005145832A
5
JP2005519871A
28
JP2005523278A
25
JP2006502184A
41
JP2006507253A
19
JP2006519264A
58
JP2006528196A
42
JP2007508039A
114
JP2007520453A
33
JP2008533018A
15
JP2008533019A
34
JP2008539832A
82
JP2009519341A
24
JP2009525790A
101
JP2009537636A
13
JP2010525083A
52
JP2011528275A
455
JP2965160B2
10
JP4527401B2
32
JP4658037B2
37
JP4663232B2
15
JP4758474B2
87
JP4787165B2
101
JP4799864B2
33
JP4818917B2
31
JPH03134050A
5
JPH03220121A
5
JPH04358132A
5
JPH04358133A
5
JPH06345625A
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
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:18:25 GMT 2023
Edited
by admin
on Fri Dec 15 17:18:25 GMT 2023
Record UNII
G9I1882VSD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FOSFESTROL SODIUM
MART.  
Common Name English
Fosfestrol tetrasodium [WHO-DD]
Common Name English
TETRASODIUM FOSFESTROL
Common Name English
FOSFESTROL TETRASODIUM SALT
MI  
Common Name English
FOSFESTROL SODIUM [MART.]
Common Name English
ANHYDROUS FOSFESTROL TETRASODIUM
Common Name English
FOSFESTROL TETRASODIUM SALT [MI]
Common Name English
FOSFESTROL TETRASODIUM
WHO-DD  
Common Name English
(E)-.ALPHA.,.ALPHA.'-DIETHYLSTILBENE-4,4'-DIOL BIS(DIHYDROGEN PHOSPHATE), TETRASODIUM SALT
Common Name English
Code System Code Type Description
RXCUI
281876
Created by admin on Fri Dec 15 17:18:25 GMT 2023 , Edited by admin on Fri Dec 15 17:18:25 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m5550
Created by admin on Fri Dec 15 17:18:25 GMT 2023 , Edited by admin on Fri Dec 15 17:18:25 GMT 2023
PRIMARY Merck Index
CAS
23519-26-8
Created by admin on Fri Dec 15 17:18:25 GMT 2023 , Edited by admin on Fri Dec 15 17:18:25 GMT 2023
ALTERNATIVE
CAS
4719-75-9
Created by admin on Fri Dec 15 17:18:25 GMT 2023 , Edited by admin on Fri Dec 15 17:18:25 GMT 2023
PRIMARY
CAS
22032-58-2
Created by admin on Fri Dec 15 17:18:25 GMT 2023 , Edited by admin on Fri Dec 15 17:18:25 GMT 2023
SUPERSEDED
EPA CompTox
DTXSID00963762
Created by admin on Fri Dec 15 17:18:25 GMT 2023 , Edited by admin on Fri Dec 15 17:18:25 GMT 2023
PRIMARY
ECHA (EC/EINECS)
225-209-6
Created by admin on Fri Dec 15 17:18:25 GMT 2023 , Edited by admin on Fri Dec 15 17:18:25 GMT 2023
PRIMARY
EVMPD
SUB02259MIG
Created by admin on Fri Dec 15 17:18:25 GMT 2023 , Edited by admin on Fri Dec 15 17:18:25 GMT 2023
PRIMARY
SMS_ID
100000087018
Created by admin on Fri Dec 15 17:18:25 GMT 2023 , Edited by admin on Fri Dec 15 17:18:25 GMT 2023
PRIMARY
PUBCHEM
3034148
Created by admin on Fri Dec 15 17:18:25 GMT 2023 , Edited by admin on Fri Dec 15 17:18:25 GMT 2023
PRIMARY
FDA UNII
G9I1882VSD
Created by admin on Fri Dec 15 17:18:25 GMT 2023 , Edited by admin on Fri Dec 15 17:18:25 GMT 2023
PRIMARY
Related Record Type Details
Structure of FOSFESTROL
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of FOSFESTROL
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