Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H18O8P2.2Na.2H |
| Molecular Weight | 472.2737 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H+].[H+].[Na+].[Na+].CC\C(=C(\CC)C1=CC=C(OP([O-])([O-])=O)C=C1)C2=CC=C(OP([O-])([O-])=O)C=C2
InChI
InChIKey=OPZDSBAHQHNXRQ-QIKYXUGXSA-L
InChI=1S/C18H22O8P2.2Na/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;2*+1/p-2/b18-17+;;
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C18H20O8P2 |
| Molecular Weight | 426.2941 |
| Charge | -2 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
DescriptionSources: http://druginfosys.com/Drug.aspx?drugCode=327&drugName=&type=0https://www.drugs.com/mmx/stilbestrol.htmlCurator'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
Sources: http://druginfosys.com/Drug.aspx?drugCode=327&drugName=&type=0https://www.drugs.com/mmx/stilbestrol.html
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
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
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL206 |
0.18 nM [EC50] | ||
Target ID: CHEMBL242 |
0.06 nM [EC50] | ||
| 10.0 µM [EC50] | |||
Target ID: CHEMBL3751 |
700.0 nM [EC50] | ||
Target ID: CHEMBL4245 |
700.0 nM [EC50] | ||
| 1.0 µM [IC50] | |||
| 1.0 µM [IC50] | |||
| 1.0 µM [IC50] | |||
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Stilphostrol Approved UseUnknown Launch Date1981 |
|||
| Primary | STILBESTROL Approved UseUsed in the treatment of prostate cancer. Launch Date1973 |
|||
| Preventing | STILBESTROL Approved UsePrevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery. Launch Date1973 |
|||
| Primary | STILBESTROL Approved UseIt is used for the treatment of senile (atrophic) vaginitis. Launch Date1973 |
|||
| Primary | STILBESTROL Approved UseIt is used for the treatment of vulvar dystrophy. Launch Date1973 |
|||
| Primary | STILBESTROL Approved UseOther therapeutic use of diethylstilbestrol was post menopause syndrome. Launch Date1973 |
|||
| Primary | STILBESTROL Approved UseDrug is indicated for replacement therapy of estrogen deficiency associated with amenorrhea. Launch Date1973 |
|||
| Primary | STILBESTROL Approved UseDrug is indicated for replacement therapy of estrogen deficiency associated with female hypogonadism. Launch Date1973 |
|||
| Preventing | STILBESTROL Approved UseDrug is indicated for the prevention of osteoporosis. Launch Date1973 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5.64 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24618069/ |
2 mg single, oral dose: 2 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIETHYLSTILBESTROL unknown | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
3672.44 pg/mL |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIETHYLSTILBESTROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
9741.84 pg × h/mL |
1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered: |
DIETHYLSTILBESTROL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
1500 mg 3 times / day multiple, oral Highest studied dose Dose: 1500 mg, 3 times / day Route: oral Route: multiple Dose: 1500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Other AEs: Anorexia, Nausea... Other AEs: Anorexia (grade 1-3, 21.6%) Sources: Nausea (grade 1-3, 44%) Vomiting (grade 1-3, 24.1%) Diarrhea (grade 1-3, 6.9%) Peri-nipple pigmentation (grade 1-3, 16.4%) Uterine bleeding (grade 1-3, 4.3%) Withdrawal bleeding (grade 1-3, 3.4%) Hypercalcemia (grade 1-3, 5.2%) Edema (grade 1-3, 18.1%) Congestive heart failure (grade 1-3, 5.2%) |
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: |
unhealthy, 56-87 |
Disc. AE: Vomiting... AEs leading to discontinuation/dose reduction: Vomiting (1 patient) Sources: |
600 mg 1 times / day multiple, oral Dose: 600 mg, 1 times / day Route: oral Route: multiple Dose: 600 mg, 1 times / day Sources: |
unhealthy, 59 |
Disc. AE: Secondary adrenocortical insufficiency... AEs leading to discontinuation/dose reduction: Secondary adrenocortical insufficiency Sources: |
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: |
unhealthy, 65 Health Status: unhealthy Age Group: 65 Sex: M Sources: |
Disc. AE: Toxic reaction (NOS), Toxic reaction (NOS)... AEs leading to discontinuation/dose reduction: Toxic reaction (NOS) (grade 2, 3 patients) Sources: Toxic reaction (NOS) (grade 3, 2 patients) |
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 Sources: |
unhealthy, 68 |
DLT: Nausea and vomiting, Nausea and vomiting... Dose limiting toxicities: Nausea and vomiting (grade 1, 13 patients) Sources: Nausea and vomiting (grade 2, 4 patients) Weight gain (2 patients) Edema (2 patients) |
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: |
unhealthy, 70 |
Other AEs: Gynecomastia, Peripheral edema... Other AEs: Gynecomastia (38%) Sources: Peripheral edema (32%) Gastrointestinal discomfort (19%) Deep vein thrombosis (8%) Skin rash (5%) Hypertension (5%) Transaminases increased (2%) |
1104 mg 1 times / day multiple, intravenous Dose: 1104 mg, 1 times / day Route: intravenous Route: multiple Dose: 1104 mg, 1 times / day Sources: |
unhealthy, 74 |
Other AEs: Nausea, Bone pain... Other AEs: Nausea (17 patients) Sources: Bone pain (17 patients) Perineal pain (1 patient) Deep vein thrombosis (4 patients) |
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: |
unhealthy |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Peri-nipple pigmentation | grade 1-3, 16.4% | 1500 mg 3 times / day multiple, oral Highest studied dose Dose: 1500 mg, 3 times / day Route: oral Route: multiple Dose: 1500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Edema | grade 1-3, 18.1% | 1500 mg 3 times / day multiple, oral Highest studied dose Dose: 1500 mg, 3 times / day Route: oral Route: multiple Dose: 1500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Anorexia | grade 1-3, 21.6% | 1500 mg 3 times / day multiple, oral Highest studied dose Dose: 1500 mg, 3 times / day Route: oral Route: multiple Dose: 1500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Vomiting | grade 1-3, 24.1% | 1500 mg 3 times / day multiple, oral Highest studied dose Dose: 1500 mg, 3 times / day Route: oral Route: multiple Dose: 1500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Withdrawal bleeding | grade 1-3, 3.4% | 1500 mg 3 times / day multiple, oral Highest studied dose Dose: 1500 mg, 3 times / day Route: oral Route: multiple Dose: 1500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Uterine bleeding | grade 1-3, 4.3% | 1500 mg 3 times / day multiple, oral Highest studied dose Dose: 1500 mg, 3 times / day Route: oral Route: multiple Dose: 1500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Nausea | grade 1-3, 44% | 1500 mg 3 times / day multiple, oral Highest studied dose Dose: 1500 mg, 3 times / day Route: oral Route: multiple Dose: 1500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Congestive heart failure | grade 1-3, 5.2% | 1500 mg 3 times / day multiple, oral Highest studied dose Dose: 1500 mg, 3 times / day Route: oral Route: multiple Dose: 1500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Hypercalcemia | grade 1-3, 5.2% | 1500 mg 3 times / day multiple, oral Highest studied dose Dose: 1500 mg, 3 times / day Route: oral Route: multiple Dose: 1500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Diarrhea | grade 1-3, 6.9% | 1500 mg 3 times / day multiple, oral Highest studied dose Dose: 1500 mg, 3 times / day Route: oral Route: multiple Dose: 1500 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| 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: |
unhealthy, 56-87 |
| 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: |
unhealthy, 59 |
| 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: |
unhealthy, 65 Health Status: unhealthy Age Group: 65 Sex: M Sources: |
| 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: |
unhealthy, 65 Health Status: unhealthy Age Group: 65 Sex: M Sources: |
| 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 Sources: |
unhealthy, 68 |
| 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 Sources: |
unhealthy, 68 |
| 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 Sources: |
unhealthy, 68 |
| 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 Sources: |
unhealthy, 68 |
| 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: |
unhealthy, 70 |
| 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: |
unhealthy, 70 |
| 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: |
unhealthy, 70 |
| 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: |
unhealthy, 70 |
| 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: |
unhealthy, 70 |
| 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: |
unhealthy, 70 |
| 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: |
unhealthy, 70 |
| 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 Sources: |
unhealthy, 74 |
| 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 Sources: |
unhealthy, 74 |
| 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 Sources: |
unhealthy, 74 |
| 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 Sources: |
unhealthy, 74 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Small nuclear RING finger protein expression during gonad development: regulation by gonadotropins and estrogen in the postnatal ovary. | 2004-05 |
|
| 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. | 2004-05 |
|
| Upregulation of angiotensin II type 2 receptor expression in estrogen-induced pituitary hyperplasia. | 2004-05 |
|
| Neonatal estrogenization leads to increased expression of cellular retinol binding protein 2 in the mouse reproductive tract. | 2004-04 |
|
| Diethylstilbestrol induces fish oocyte maturation. | 2004-03-09 |
|
| Long-term alteration of gene expression without morphological change in testis after neonatal exposure to genistein in mice: toxicogenomic analysis using cDNA microarray. | 2004-03 |
|
| Modulation of AhR-mediated CYP1A1 mRNA and EROD activities by 17beta-estradiol and dexamethasone in TCDD-induced H411E cells. | 2004-03 |
|
| Dimerization modulates the activity of the orphan nuclear receptor ERRgamma. | 2004-02-20 |
|
| Comparison of the Hershberger assay and androgen receptor binding assay of twelve chemicals. | 2004-02-15 |
|
| Identification of estrogen-responsive genes by complementary deoxyribonucleic acid microarray and characterization of a novel early estrogen-induced gene: EEIG1. | 2004-02 |
|
| 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. | 2004-01 |
|
| Toxicogenomic difference between diethylstilbestrol and 17beta-estradiol in mouse testicular gene expression by neonatal exposure. | 2004-01 |
|
| The inhibitory effects of flavonoids and antiestrogens on the Glut1 glucose transporter in human erythrocytes. | 2003-12-15 |
|
| The immune system of geriatric mice is modulated by estrogenic endocrine disruptors (diethylstilbestrol, alpha-zearalanol, and genistein): effects on interferon-gamma. | 2003-12-15 |
|
| Limb reduction defects in the first generation and deafness in the second generation of intrauterine exposed fetuses to diethylstilbestrol. | 2003-12-09 |
|
| Effect of diethylstilbestrol on polyamine metabolism in hamster epididymis. | 2003-12 |
|
| Similarities and differences in uterine gene expression patterns caused by treatment with physiological and non-physiological estrogens. | 2003-12 |
|
| 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. | 2003-11-07 |
|
| Effects of endocrine disrupting compounds on the pathology and oestrogen receptor alpha and beta distribution in the uterus and cervix of ewe lambs. | 2003-11 |
|
| 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. | 2003-10-24 |
|
| The effect of endocrine disrupting chemicals on thyroid hormone binding to Japanese quail transthyretin and thyroid hormone receptor. | 2003-10-15 |
|
| Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003-10 |
|
| Neonatal diethylstilbestrol exposure induces persistent elevation of c-fos expression and hypomethylation in its exon-4 in mouse uterus. | 2003-10 |
|
| Autocrine/paracrine action of pituitary vasoactive intestinal peptide on lactotroph hyperplasia induced by estrogen. | 2003-10 |
|
| Sulfonation of environmental estrogens by zebrafish cytosolic sulfotransferases. | 2003-09-12 |
|
| Cirrhosis with steatohepatitis following longterm stilboestrol treatment. | 2003-08 |
|
| Estrogenic endocrine disruptive components interfere with calcium handling and differentiation of human trophoblast cells. | 2003-07-01 |
|
| Cytotoxic and xenoestrogenic effects via biotransformation of trans-anethole on isolated rat hepatocytes and cultured MCF-7 human breast cancer cells. | 2003-07-01 |
|
| In vitro modulation of prolactin mRNA by toxaphene and 3,3',4,4'-tetrachlorobiphenyl. | 2003-07 |
|
| Update on cryptorchidism: endocrine, environmental and therapeutic aspects. | 2003-06 |
|
| Activation of estrogen receptor alpha and ERbeta by 4-methylbenzylidene-camphor in human and rat cells: comparison with phyto- and xenoestrogens. | 2003-04-30 |
|
| Differential expression of c-fos and c-myc protooncogenes by estrogens, xenobiotics and other growth-stimulatory agents in primary rat hepatocytes. | 2003-03 |
|
| 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. | 2003-03 |
|
| Quantitative structure-activity relationships for estrogen receptor binding affinity of phenolic chemicals. | 2003-03 |
|
| Diethylstilbestrol induces rat spermatogenic cell apoptosis in vivo through increased expression of spermatogenic cell Fas/FasL system. | 2003-02-21 |
|
| Endocrine disrupting chemicals: interference of thyroid hormone binding to transthyretins and to thyroid hormone receptors. | 2003-01-31 |
|
| Long-lasting effects of lindane on mouse spermatogenesis induced by in utero exposure. | 2003-01-01 |
|
| Oxidative DNA damage induced by toluene is involved in its male reproductive toxicity. | 2003-01 |
|
| Simulation of the different biological activities of diethylstilbestrol (DES) on estrogen receptor alpha and estrogen-related receptor gamma. | 2003-01 |
|
| Improvement of a sensitive enzyme-linked immunosorbent assay for screening estrogen receptor binding activity. | 2002-12 |
|
| Increases in mouse uterine heat shock protein levels are a sensitive and specific response to uterotrophic agents. | 2002-12 |
|
| 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. | 2002-12 |
|
| Responsiveness of endometrial genes Connexin26, Connexin43, C3 and clusterin to primary estrogen, selective estrogen receptor modulators, phyto- and xenoestrogens. | 2002-10 |
|
| Modulation of the onset of postnatal development of H(+)-ATPase-rich cells by steroid hormones in rat epididymis. | 2002-10 |
|
| 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. | 2002-08-15 |
|
| Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids. | 2002-07 |
|
| Estrogen receptor binding assay of chemicals with a surface plasmon resonance biosensor. | 2002-05 |
|
| Effect of mesulergine on prolactin secretion and dopamine D2 receptors-adaptive changes in diethylstilbestrol-induced hyperplasia of the rat anterior pituitary. | 1992-03 |
|
| Induction of urogenital anomalies and some tumors in the progeny of mice receiving diethylstilbestrol during pregnancy. | 1977-04 |
|
| Clear cell adenocarcinoma of the cervix and vagina. A clinicopathologic study of 21 cases with and without a history of maternal ingestion of estrogens. | 1976-02 |
Patents
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
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m5550
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76970428
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