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Overview
| Generic Names: | DEB; DES; Diethylstilbesterol; Diethylstilbestrol BP; Diethylstilboesterol; Dietilestilbestrol; Percutatrine oestrogenique iscovesco; Rcra waste number U089; trans-Diethylstilbesterol; trans-Diethylstilbestrol; trans-Diethylstilboesterol |
|---|---|
| Trade Names: | Acnestrol; Agostilben; Antigestil; Bio-des; Bufon; Climaterine; Comestrol; Comestrol estrobene; Cyren; Cyren A; Dawe's destrol; Desma; Destrol; Di-Estryl; DiBestrol 2 Premix; Diastyl; Dibestrol; Dicorvin; Distilbene; Domestrol; Dyestrol; Estilben; Estilbin MCO; Estril; Estrobene; Estrogenine; Estromenin; Estrosyn; Follidiene; Fonatol; Grafestrol; Gynopharm; Hi-Bestrol; Idroestril; Iscovesco; Makarol; Menostilbeen; Micrest; Microest; Milestrol; Neo-Oestranol I; New-Estranol 1; OeKolp; Oestrogenine; Oestrol vetag; Oestromenin; Oestromensil; Oestromensyl; Oestromienin; Oestromon; Pabestrol; Palestrol; Protectona; Rumestrol 1; Rumestrol 2; Sedestran; Serral; Sexocretin; Sibol; Sintestrol; Stibilium; Stil; Stil-Rol; Stilbestroform; Stilbestrol; Stilbestrone; Stilbetin; Stilboefral; Stilboestroform; Stilboestrol; Stilbofolin; Stilbofollin; Stilbol; Stilkap; Stilphostrol; Synestrin; Synthestrin; Synthoestrin; Synthofolin; Syntofolin; Tampovagan stilboestrol; Tylosterone; Vagestrol; neo-Oestranol 1; strobene |
| PharmGKB Accession Id: | PA449307 |
Description
A synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen. (Merck, 11th ed) (source: Drug Bank)
Indication
Used in the treatment of prostate cancer. Previously used in the prevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery. (source: Drug Bank)
ATC Therapeutic Categories
- G03CB:Synthetic estrogens, plain
- G03CC:Estrogens, combinations with other drugs
- L02AA:Estrogens
Pharmacology, Interactions, and Contraindications
Mechanism Of Action
Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH). (source: Drug Bank)
Pharmacology
Diethylstilbestrol is a synthetic estrogen that was developed to supplement a woman's natural estrogen production. In 1971, the Food and Drug Administration (FDA) issued a Drug Bulletin advising physicians to stop prescribing DES to pregnant women because it was linked to a rare vaginal cancer in female offspring. (source: Drug Bank)
Absorption, Distribution, Metabolism, Elimination & Toxicity
Biotransformation
Hepatic. (source: Drug Bank)
Toxicity
Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females. (source: Drug Bank)
Isomeric SMILES Code:
CC/C(=C(/CC)\c1ccc(cc1)O)/c2ccc(cc2)O (source: Drug Bank)
The following genes are in curated knowledge about this drug.
| Gene | Relationship | Evidence | |
|---|---|---|---|
|
NR1I2 |
|
Publications |
A list of non-curated publications that mention this drug along with other genes is available.
Drug Targets
| Gene | Description | |
|---|---|---|
| ESR1 |
|
(source: Drug Bank) |
| ESRRG |
|
(source: Drug Bank) |
| TTR |
|
(source: Drug Bank) |
BioCarta Pathways†
- carm1 and regulation of the estrogen receptor - (BioCarta via Pathway Interaction Database)
- downregulated of mta-3 in er-negative breast tumors - (BioCarta via Pathway Interaction Database)
- estrogen responsive protein efp controls cell cycle and breast tumors growth - (BioCarta via Pathway Interaction Database)
- overview of telomerase protein component gene htert transcriptional regulation - (BioCarta via Pathway Interaction Database)
- pelp1 modulation of estrogen receptor activity - (BioCarta via Pathway Interaction Database)
Reactome Pathways†
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| Drug | Description | |
|---|---|---|
| amobarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| butalbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| griseofulvin |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| hexobarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| mephenytoin |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| methylphenobarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| pentobarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| phenobarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| phenytoin |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| prednisolone |
|
The estrogenic agent increases the effect of corticosteroid (source: Drug Bank) |
| prednisone |
|
The estrogenic agent increases the effect of corticosteroid (source: Drug Bank) |
| primidone |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| raloxifene |
|
Association not recommended (source: Drug Bank) |
| ursodeoxycholic acid |
|
Estrogens decreases the effect of ursodiol (source: Drug Bank) |
Non-Curated Information
A list of non-curated publications that mention this drug along with other diseases is available.
Additional Datasets
These datasets are minimally curated and are sorted alphabetically by title.
LinkOuts
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.