QuickView for Diethylstilbestrol (compound)

Summary
General Info

PubChem

PubChem Compound 3037262

Name:	Diethylstilbestrol
PubChem Compound ID:	3037262
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)
Molecular formula:	C₁₈H₁₈Na₂O₂
Molecular weight:	312.314 g/mol
Synonyms:	4,4'-Stilbenediol, alpha,alpha'-diethyl-, disodium salt; 63528-82-5; 56-53-1; Diethylstilbestrol disodium salt; DES disodium salt; alpha,alpha'-Diethyl-4,4'-stilbenediol disodium salt

DrugBank

Identification

Name:	Diethylstilbestrol
Name (isomeric):	DB00255
Drug Type:	small molecule
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)
Synonyms:	DEB; Percutatrine oestrogenique iscovesco; Rcra waste number U089; trans-Diethylstilbesterol; DES; Diethylstilboesterol; trans-Diethylstilbestrol; trans-Diethylstilboesterol; Dietilestilbestrol; Diethylstilbesterol. show more » DEB; Percutatrine oestrogenique iscovesco; Rcra waste number U089; trans-Diethylstilbesterol; DES; Diethylstilboesterol; trans-Diethylstilbestrol; trans-Diethylstilboesterol; Dietilestilbestrol; Diethylstilbesterol; Diethylstilbestrol BP show less «
Brand:	Rumestrol 1, Sedestran, Rumestrol 2, Estrogenine, Estilben, Estrobene, Stilboefral, Hi-Bestrol, Dibestrol, Tylosterone, DiBestrol 2 Premix, Iscovesco, Gynopharm, Oestromensil, Stilbol, Follidiene, Comestrol, Estromenin, Fonatol, Synthoestrin, Di-Estryl, Estril, Acnestrol, Oestrogenine, Diastyl, OeKolp, Synthestrin, Oestromenin, Cyren, Idroestril, Dyestrol, strobene, Stilbetin, Bio-des, Micrest, Menostilbeen, Sexocretin, Stilbofolin, Comestrol estrobene, Synthofolin, Serral, Agostilben, Oestromienin, Syntofolin, Stilbestroform, Bufon, Antigestil, Pabestrol, Stilbestrone, Destrol, Stilbestrol, Tampovagan stilboestrol, Stilphostrol, Stibilium, Neo-Oestranol I, Protectona, Stilboestrol, Makarol, neo-Oestranol 1, Sintestrol, Domestrol, Milestrol, Synestrin, New-Estranol 1, Stil-Rol, Sibol, Stilbofollin, Palestrol, Estilbin MCO, Oestrol vetag, Vagestrol, Oestromon, Dicorvin, Desma, Distilbene, Stil, Stilboestroform, Climaterine, Cyren A, Microest, Oestromensyl, Grafestrol, Stilkap, Dawe's destrol, Estrosyn
Category:	Antineoplastic Agents, Hormonal, Estrogens, Non-Steroidal, Carcinogens
CAS number:	56-53-1

Pharmacology

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.
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.
Mechanism of Action:	Estrogens diffuse into their target cells and interact with a protein receptor, the estrogen receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. The effect of Estrogen binding their receptors causes downstream increases the hepatic synthesis of sex hormone binding globulin (SHBG), th... show more » Estrogens diffuse into their target cells and interact with a protein receptor, the estrogen receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. The effect of Estrogen binding their receptors causes downstream increases 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). show less «
Biotransformation:	Hepatic.
Toxicity:	Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
Affected organisms:	Humans and other mammals

Interactions

Drug interaction:

Talbutal	The enzyme inducer, talbutal, decreases the effect of the hormone agent, diethylstilbestrol.
Butethal	The enzyme inducer, butethal, decreases the effect of the hormone agent, diethylstilbestrol.
Heptabarbital	The enzyme inducer, heptabarbital, decreases the effect of the hormone agent, diethylstilbestrol.
Methylphenobarbital	The enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, diethylstilbestrol.
Prednisone	The estrogenic agent, diethylstilbestrol, may increase the effect of corticosteroid, prednisone.

Talbutal	The enzyme inducer, talbutal, decreases the effect of the hormone agent, diethylstilbestrol.
Butethal	The enzyme inducer, butethal, decreases the effect of the hormone agent, diethylstilbestrol.
Heptabarbital	The enzyme inducer, heptabarbital, decreases the effect of the hormone agent, diethylstilbestrol.
Methylphenobarbital	The enzyme inducer, methylphenobarbital, decreases the effect of the hormone agent, diethylstilbestrol.
Prednisone	The estrogenic agent, diethylstilbestrol, may increase the effect of corticosteroid, prednisone.
Mephenytoin	The enzyme inducer, mephenytoin, decreases the effect of the hormone agent, diethylstilbestrol.
Methohexital	The enzyme inducer, methohexital, decreases the effect of the hormone agent, diethylstilbestrol.
Tipranavir	Diethylstilbestrol may increase the adverse dermatological effects (i.e. skin rash) of Tipranavir. Tipranavir may decrease the serum concentration Diethylstilbestrol. Monitor estrogen levels during concomitant therapy.
Fosphenytoin	The enzyme inducer, fosphenytoin, may decrease the therapeutic effect of diethylstilbestrol.
Butabarbital	The enzyme inducer, butabarbital, decreases the effect of the hormone agent, diethylstilbestrol.
Griseofulvin	The enzyme inducer, griseofulvin, decreases the effect of the hormone agent, diethylstilbestrol.
Secobarbital	The enzyme inducer, secobarbital, decreases the effect of the hormone agent, diethylstilbestrol.
Raloxifene	Association not recommended
Prednisolone	The estrogenic agent, diethylstilbestrol, may increase the effect of the corticosteroid, prednisolone.
Phenytoin	The enzyme inducer, phenytoin, decreases the effect of the hormone agent, diethylstilbestrol.
Aprobarbital	The enzyme inducer, aprobarbital, decreases the effect of the hormone agent, diethylstilbestrol.
Butalbital	The enzyme inducer, butalbital, decreases the effect of the hormone agent, diethylstilbestrol.
Hexobarbital	The enzyme inducer, hexobarbital, decreases the effect of the hormone agent, diethylstilbestrol.
Ursodeoxycholic acid	Estrogens decreases the effect of ursodiol
Amobarbital	The enzyme inducer, amobarbital, decreases the effect of the hormone agent, diethylstilbestrol.
Primidone	The enzyme inducer, primidone, may decrease the effect of the hormone agent, diethylstilbestrol.
Phenobarbital	The enzyme inducer, phenobarbital, may decrease the therapeutic effect of diethylstilbestrol.
Ethotoin	The enzyme inducer, ethotoin, decreases the effect of the hormone agent, diethylstilbestrol.
Pentobarbital	The enzyme inducer, pentobarbital, decreases the effect of the hormone agent, diethylstilbestrol.

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Targets

Estrogen receptor

Estrogen-related receptor gamma

Estrogen receptor beta

Enzymes

Catechol O-methyltransferase

Transporters

ATP-binding cassette sub-family G member 2

Multidrug resistance protein 1

Carriers

Transthyretin

UniProt ID:	P02766
Gene:	TTR