Identification

Name
Diethylstilbestrol
Accession Number
DB00255  (APRD00920, EXPT01164)
Type
Small Molecule
Groups
Approved, Investigational
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)

Structure
Thumb
Synonyms
  • (E)-3,4-bis(4-hydroxyphenyl)-3-hexene
  • (e)-4,4'-(1,2-Diethyl-1,2-ethenediyl)bisphenol
  • 4,4'-Dihydroxy-alpha,beta-diethylstilbene
  • 4,4'-dihydroxy-α,β-diethylstilbene
  • alpha,Alpha'-diethyl-(e)-4,4'-stilbenediol
  • DES
  • Diethylstilbestrol
  • Diethylstilbestrolum
  • Dietilestilbestrol
  • Distilbene
  • Stilboestrol
  • trans-4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenol
  • trans-Diethylstilbesterol
  • trans-Diethylstilbestrol
  • trans-Diethylstilboesterol
  • α,α'-diethyl-(E)-4,4'-stilbenediol
External IDs
RCRA waste number U089
Product Ingredients
IngredientUNIICASInChI Key
Diethylstilbestrol diphosphateA0E0NMA80F522-40-7NLORYLAYLIXTID-ISLYRVAYSA-N
Diethylstilbestrol diphosphate sodiumNot AvailableNot AvailableNot applicable
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Honvol Ampoules 250mgLiquid250 mgIntravenousCarter Horner Corp.1956-12-312000-11-17Canada
Honvol Tablets 100mgTablet100 mgOralCarter Horner Corp.1958-12-312001-05-22Canada
Stilbestrol 0.5mg TabletTablet.5 mgOralGlaxo Canada Inc1993-12-311998-07-30Canada
Stilbestrol 1.0mg TabletTablet1 mgOralGlaxo Canada Inc1991-12-311996-09-10Canada
Stilbestrol Tab 1mgTablet1 mgOralEverest Pharmaceuticals Ltd.1980-12-311999-07-14Canada
Stilbestrol Tablets 0.1 mgTablet0.105 mgOralWell Spring Pharmaceutical Corporation1996-07-302009-02-23Canada
Stilbestrol Tablets 0.5 mgTablet0.51 mgOralWell Spring Pharmaceutical Corporation1997-04-022009-02-23Canada
Stilbestrol Tablets 1.0 mgTablet1.0 mgOralWell Spring Pharmaceutical Corporation1996-07-302009-02-23Canada
Stilboestrol Tab 0.1mgTablet.1 mgOralAllen & Hanburys A Glaxo Canada Ltd. Co.1951-12-311996-09-10Canada
Stilboestrol Tab 0.5mgTablet.5 mgOralAllen & Hanburys A Glaxo Canada Ltd. Co.1951-12-311996-09-20Canada
International/Other Brands
Distilbene (Gerda) / Stilbestrol (Nysco) / Stilbetin (Bristol Myers-Squibb)
Categories
UNII
731DCA35BT
CAS number
56-53-1
Weight
Average: 268.3502
Monoisotopic: 268.146329884
Chemical Formula
C18H20O2
InChI Key
RGLYKWWBQGJZGM-ISLYRVAYSA-N
InChI
InChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17+
IUPAC Name
4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
SMILES
CCC(=C(CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

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.

Structured Indications
Not Available
Pharmacodynamics

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), 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).

TargetActionsOrganism
AEstrogen receptor alpha
agonist
Human
AEstrogen-related receptor gamma
agonist
Human
AEstrogen receptor beta
agonist
Human
USteroid hormone receptor ERR1Not AvailableHuman
USteroid hormone receptor ERR2Not AvailableHuman
UNuclear receptor coactivator 2Not AvailableHuman
UNuclear receptor subfamily 1 group I member 2Not AvailableHuman
UAndrogen receptor
antagonist
Human
USex hormone-binding globulinNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe serum concentration of Diethylstilbestrol can be decreased when it is combined with 1,10-Phenanthroline.Experimental
16-BromoepiandrosteroneThe serum concentration of 16-Bromoepiandrosterone can be increased when it is combined with Diethylstilbestrol.Investigational
19-norandrostenedioneThe serum concentration of 19-norandrostenedione can be increased when it is combined with Diethylstilbestrol.Experimental, Illicit
3,4-DichloroisocoumarinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with 3,4-Dichloroisocoumarin.Experimental
4-(2-Aminoethyl)Benzenesulfonyl FluorideThe serum concentration of Diethylstilbestrol can be decreased when it is combined with 4-(2-Aminoethyl)Benzenesulfonyl Fluoride.Experimental
5-androstenedioneThe serum concentration of 5-androstenedione can be increased when it is combined with Diethylstilbestrol.Experimental, Illicit
AbciximabDiethylstilbestrol may decrease the anticoagulant activities of Abciximab.Approved
AcenocoumarolDiethylstilbestrol may decrease the anticoagulant activities of Acenocoumarol.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Diethylstilbestrol.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Diethylstilbestrol.Experimental
AcitretinThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Acitretin.Approved
AdapaleneThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Adapalene.Approved
AlclometasoneThe serum concentration of Alclometasone can be increased when it is combined with Diethylstilbestrol.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Diethylstilbestrol.Experimental, Investigational
AlitretinoinThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Alitretinoin.Approved, Investigational
AlogliptinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Alpha-1-proteinase inhibitor.Approved
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be increased when it is combined with Diethylstilbestrol.Experimental, Investigational
AmcinonideThe serum concentration of Amcinonide can be increased when it is combined with Diethylstilbestrol.Approved
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Diethylstilbestrol.Approved
AmobarbitalThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Amobarbital.Approved, Illicit
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Diethylstilbestrol.Approved, Investigational
AmprenavirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Amprenavir.Approved
AnastrozoleThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Diethylstilbestrol.Approved, Investigational
AncrodDiethylstilbestrol may decrease the anticoagulant activities of Ancrod.Investigational
AndrostenedioneThe serum concentration of Androstenedione can be increased when it is combined with Diethylstilbestrol.Experimental, Illicit
AnecortaveThe serum concentration of Anecortave can be increased when it is combined with Diethylstilbestrol.Investigational
anecortave acetateThe serum concentration of anecortave acetate can be increased when it is combined with Diethylstilbestrol.Investigational
Anthrax immune globulin humanDiethylstilbestrol may increase the thrombogenic activities of Anthrax immune globulin human.Approved
Antithrombin III humanThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Antithrombin III human.Approved
ApixabanThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Apixaban.Approved
AprepitantThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Aprepitant.Approved, Investigational
AprotininThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Aprotinin.Approved, Withdrawn
ArdeparinDiethylstilbestrol may decrease the anticoagulant activities of Ardeparin.Approved, Investigational, Withdrawn
ArgatrobanThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Argatroban.Approved, Investigational
ArmodafinilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Armodafinil.Approved, Investigational
ArtemetherThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Artemether.Approved
ArtesunateThe serum concentration of the active metabolites of Artesunate can be reduced when Artesunate is used in combination with Diethylstilbestrol resulting in a loss in efficacy.Approved, Investigational
AsunaprevirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Asunaprevir.Approved, Investigational
AtamestaneThe serum concentration of Atamestane can be increased when it is combined with Diethylstilbestrol.Investigational
AtazanavirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Atazanavir.Approved, Investigational
AtorvastatinThe risk or severity of adverse effects can be increased when Diethylstilbestrol is combined with Atorvastatin.Approved
BarbexacloneThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Barbexaclone.Experimental
BarbitalThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Barbital.Illicit
BatimastatThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Batimastat.Experimental
BecaplerminDiethylstilbestrol may decrease the anticoagulant activities of Becaplermin.Approved, Investigational
Beclomethasone dipropionateThe serum concentration of Beclomethasone dipropionate can be increased when it is combined with Diethylstilbestrol.Approved, Investigational
BenazeprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Benazepril.Approved, Investigational
BenzamidineThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Benzamidine.Experimental
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Diethylstilbestrol.Approved, Vet Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Diethylstilbestrol.Approved, Investigational
BexaroteneThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Bexarotene.Approved, Investigational
BivalirudinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Boceprevir.Approved, Withdrawn
BosentanThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Diethylstilbestrol.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Diethylstilbestrol.Approved, Investigational
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Diethylstilbestrol.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Diethylstilbestrol.Approved
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Diethylstilbestrol.Approved
CamostatThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Camostat.Experimental
CandoxatrilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Candoxatrilat.Experimental
Capromab pendetideDiethylstilbestrol may decrease effectiveness of Capromab pendetide as a diagnostic agent.Approved
CaptoprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Captopril.Approved
CarbamazepineThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Carbamazepine.Approved, Investigational
CelecoxibCelecoxib may increase the thrombogenic activities of Diethylstilbestrol.Approved, Investigational
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Diethylstilbestrol.Withdrawn
CertoparinDiethylstilbestrol may decrease the anticoagulant activities of Certoparin.Approved, Investigational
Chenodeoxycholic acidThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Diethylstilbestrol.Approved
CholesterolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Cholesterol.Experimental, Investigational
CholestyramineThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Cholestyramine.Approved
ChymostatinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Chymostatin.Experimental
CiclesonideThe serum concentration of Ciclesonide can be increased when it is combined with Diethylstilbestrol.Approved, Investigational
CilastatinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Cilastatin.Approved
CilazaprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Cilazapril.Approved
Citric AcidDiethylstilbestrol may decrease the anticoagulant activities of Citric Acid.Approved, Nutraceutical, Vet Approved
ClobazamThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Clobazam.Approved, Illicit
ClobetasolThe serum concentration of Clobetasol can be increased when it is combined with Diethylstilbestrol.Investigational
Clobetasol propionateThe serum concentration of Clobetasol propionate can be increased when it is combined with Diethylstilbestrol.Approved
ClobetasoneThe serum concentration of Clobetasone can be increased when it is combined with Diethylstilbestrol.Approved
ClocortoloneThe serum concentration of Clocortolone can be increased when it is combined with Diethylstilbestrol.Approved
ClorindioneDiethylstilbestrol may decrease the anticoagulant activities of Clorindione.Experimental
CobicistatThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Cobicistat.Approved
ColesevelamThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Colestipol.Approved
Conestat alfaDiethylstilbestrol may increase the thrombogenic activities of Conestat alfa.Approved
Cortexolone 17α-propionateThe serum concentration of Cortexolone 17α-propionate can be increased when it is combined with Diethylstilbestrol.Investigational
CorticosteroneThe serum concentration of Corticosterone can be increased when it is combined with Diethylstilbestrol.Experimental
Cortisone acetateThe serum concentration of Cortisone acetate can be increased when it is combined with Diethylstilbestrol.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Diethylstilbestrol.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Diethylstilbestrol.Experimental
Dabigatran etexilateThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Dabigatran etexilate.Approved
DabrafenibThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Dabrafenib.Approved
DalteparinDiethylstilbestrol may decrease the anticoagulant activities of Dalteparin.Approved
DanaparoidDiethylstilbestrol may decrease the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarexabanThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Darexaban.Investigational
DarunavirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Darunavir.Approved
DeflazacortThe serum concentration of Deflazacort can be increased when it is combined with Diethylstilbestrol.Approved
DelanzomibThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Delanzomib.Investigational
DelaprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Delapril.Experimental
DesirudinDiethylstilbestrol may decrease the anticoagulant activities of Desirudin.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Diethylstilbestrol.Approved
DesonideThe serum concentration of Desonide can be increased when it is combined with Diethylstilbestrol.Approved, Investigational
DesoximetasoneThe serum concentration of Desoximetasone can be increased when it is combined with Diethylstilbestrol.Approved
Desoxycorticosterone acetateThe serum concentration of Desoxycorticosterone acetate can be increased when it is combined with Diethylstilbestrol.Approved
Desoxycorticosterone PivalateThe serum concentration of Desoxycorticosterone Pivalate can be increased when it is combined with Diethylstilbestrol.Experimental, Vet Approved
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Diethylstilbestrol.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe serum concentration of Dexamethasone isonicotinate can be increased when it is combined with Diethylstilbestrol.Vet Approved
DextranDiethylstilbestrol may decrease the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Diethylstilbestrol may decrease the anticoagulant activities of Dextran 40.Approved
Dextran 70Diethylstilbestrol may decrease the anticoagulant activities of Dextran 70.Approved
Dextran 75Diethylstilbestrol may decrease the anticoagulant activities of Dextran 75.Approved
DicoumarolDiethylstilbestrol may decrease the anticoagulant activities of Dicoumarol.Approved
DiflorasoneThe serum concentration of Diflorasone can be increased when it is combined with Diethylstilbestrol.Approved
DifluocortoloneThe serum concentration of Difluocortolone can be increased when it is combined with Diethylstilbestrol.Approved, Investigational
DifluprednateThe serum concentration of Difluprednate can be increased when it is combined with Diethylstilbestrol.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Diethylstilbestrol.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Diethylstilbestrol.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Diethylstilbestrol.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Diethylstilbestrol.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Diethylstilbestrol.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Diethylstilbestrol.Experimental
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Diethylstilbestrol.Approved
DiphenadioneDiethylstilbestrol may decrease the anticoagulant activities of Diphenadione.Experimental
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Diethylstilbestrol.Approved, Investigational
DyphyllineThe serum concentration of Dyphylline can be increased when it is combined with Diethylstilbestrol.Approved
EcabetThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Ecabet.Approved, Investigational
Edetic AcidDiethylstilbestrol may decrease the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Edoxaban.Approved
ElafinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Elafin.Investigational
ElvitegravirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Elvitegravir.Approved
EnalaprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Enalkiren.Experimental
EnoxaparinDiethylstilbestrol may decrease the anticoagulant activities of Enoxaparin.Approved
EntacaponeThe metabolism of Diethylstilbestrol can be decreased when combined with Entacapone.Approved, Investigational
Epigallocatechin GallateThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Epigallocatechin Gallate.Investigational
EquileninThe serum concentration of Equilenin can be increased when it is combined with Diethylstilbestrol.Experimental
EquilinThe serum concentration of Equilin can be increased when it is combined with Diethylstilbestrol.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Diethylstilbestrol.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Diethylstilbestrol.Approved
Eslicarbazepine acetateThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Diethylstilbestrol.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be increased when it is combined with Diethylstilbestrol.Approved
Ethyl biscoumacetateDiethylstilbestrol may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacEtodolac may increase the thrombogenic activities of Diethylstilbestrol.Approved, Investigational, Vet Approved
EtoricoxibEtoricoxib may increase the thrombogenic activities of Diethylstilbestrol.Approved, Investigational
ExemestaneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Diethylstilbestrol.Approved, Investigational
ExenatideThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Exenatide.Approved, Investigational
FaldaprevirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Faldaprevir.Investigational
FelbamateThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Felbamate.Approved
Ferulic acidDiethylstilbestrol may decrease the anticoagulant activities of Ferulic acid.Experimental
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Diethylstilbestrol.Approved
fluasteroneThe serum concentration of fluasterone can be increased when it is combined with Diethylstilbestrol.Investigational
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Diethylstilbestrol.Approved
FluindioneDiethylstilbestrol may decrease the anticoagulant activities of Fluindione.Investigational
FlumethasoneThe serum concentration of Flumethasone can be increased when it is combined with Diethylstilbestrol.Approved, Vet Approved
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Diethylstilbestrol.Approved, Investigational
Fluocinolone AcetonideThe serum concentration of Fluocinolone Acetonide can be increased when it is combined with Diethylstilbestrol.Approved, Investigational, Vet Approved
FluocinonideThe serum concentration of Fluocinonide can be increased when it is combined with Diethylstilbestrol.Approved, Investigational
FluocortoloneThe serum concentration of Fluocortolone can be increased when it is combined with Diethylstilbestrol.Approved, Withdrawn
FluorometholoneThe serum concentration of Fluorometholone can be increased when it is combined with Diethylstilbestrol.Approved
FluprednideneThe serum concentration of Fluprednidene can be increased when it is combined with Diethylstilbestrol.Approved, Withdrawn
FluprednisoloneThe serum concentration of Fluprednisolone can be increased when it is combined with Diethylstilbestrol.Approved
FlurandrenolideThe serum concentration of Flurandrenolide can be increased when it is combined with Diethylstilbestrol.Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Diethylstilbestrol.Approved
Fluticasone propionateThe serum concentration of Fluticasone propionate can be increased when it is combined with Diethylstilbestrol.Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Diethylstilbestrol.Approved
FondaparinuxDiethylstilbestrol may decrease the anticoagulant activities of Fondaparinux.Investigational
Fondaparinux sodiumDiethylstilbestrol may decrease the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
FormestaneThe serum concentration of Formestane can be increased when it is combined with Diethylstilbestrol.Approved, Investigational, Withdrawn
FosamprenavirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Fosaprepitant.Approved
FosinoprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Fosinopril.Approved
FosphenytoinThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Fosphenytoin.Approved
GabexateThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Gabexate.Investigational
GeldanamycinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Geldanamycin.Experimental, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Diethylstilbestrol.Experimental
GM6001The serum concentration of Diethylstilbestrol can be decreased when it is combined with GM6001.Experimental
GriseofulvinThe metabolism of Diethylstilbestrol can be increased when combined with Griseofulvin.Approved, Vet Approved
HalcinonideThe serum concentration of Halcinonide can be increased when it is combined with Diethylstilbestrol.Approved, Investigational, Withdrawn
HE3286The serum concentration of HE3286 can be increased when it is combined with Diethylstilbestrol.Investigational
HeparinDiethylstilbestrol may decrease the anticoagulant activities of Heparin.Approved, Investigational
HexobarbitalThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Hexobarbital.Approved
Human C1-esterase inhibitorDiethylstilbestrol may increase the thrombogenic activities of Human C1-esterase inhibitor.Approved
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Diethylstilbestrol.Approved, Investigational
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Diethylstilbestrol.Approved, Vet Approved
IdraparinuxThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Idraparinux.Investigational
ImidaprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Imidapril.Investigational
IndinavirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Indinavir.Approved
IsoflurophateThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Isoflurophate.Approved, Investigational, Withdrawn
IsotretinoinThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Isotretinoin.Approved
IstaroximeThe serum concentration of Istaroxime can be increased when it is combined with Diethylstilbestrol.Investigational
IxazomibThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Ixazomib.Approved
LamotrigineThe serum concentration of Lamotrigine can be decreased when it is combined with Diethylstilbestrol.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Diethylstilbestrol.Experimental
LenalidomideDiethylstilbestrol may increase the thrombogenic activities of Lenalidomide.Approved
LepirudinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Lepirudin.Approved
LetaxabanThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Letaxaban.Investigational
LevothyroxineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Diethylstilbestrol.Approved
LinagliptinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Linagliptin.Approved
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Diethylstilbestrol.Approved, Vet Approved
LiotrixThe therapeutic efficacy of Liotrix can be decreased when used in combination with Diethylstilbestrol.Approved
LisinoprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Lisinopril.Approved, Investigational
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Diethylstilbestrol.Approved, Investigational
LopinavirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Lopinavir.Approved
LoteprednolThe serum concentration of Loteprednol can be increased when it is combined with Diethylstilbestrol.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Diethylstilbestrol.Approved, Investigational
LumacaftorThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Lumacaftor.Approved
LumiracoxibLumiracoxib may increase the thrombogenic activities of Diethylstilbestrol.Approved, Investigational
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Diethylstilbestrol.Illicit, Investigational, Withdrawn
ME-609The serum concentration of ME-609 can be increased when it is combined with Diethylstilbestrol.Investigational
MedrysoneThe serum concentration of Medrysone can be increased when it is combined with Diethylstilbestrol.Approved
MelagatranThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Melagatran.Experimental
MelengestrolThe serum concentration of Melengestrol can be increased when it is combined with Diethylstilbestrol.Vet Approved
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Diethylstilbestrol.Experimental
MethohexitalThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Methohexital.Approved
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Diethylstilbestrol.Approved
MethylphenobarbitalThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Methylphenobarbital.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Diethylstilbestrol.Approved, Vet Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Diethylstilbestrol.Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Diethylstilbestrol.Experimental
MetreleptinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Metreleptin.Approved
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Diethylstilbestrol.Experimental
MifepristoneThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Mifepristone.Approved, Investigational
ModafinilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Modafinil.Approved, Investigational
MoexiprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Moexipril.Approved
MometasoneThe serum concentration of Mometasone can be increased when it is combined with Diethylstilbestrol.Approved, Vet Approved
Mycophenolic acidThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Mycophenolic acid.Approved
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Diethylstilbestrol can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NabumetoneNabumetone may increase the thrombogenic activities of Diethylstilbestrol.Approved
NadroparinDiethylstilbestrol may decrease the anticoagulant activities of Nadroparin.Approved
NafamostatThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Nafamostat.Approved, Investigational
NafcillinThe metabolism of Diethylstilbestrol can be increased when combined with Nafcillin.Approved
NCX 1022The serum concentration of NCX 1022 can be increased when it is combined with Diethylstilbestrol.Investigational
NelfinavirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Nelfinavir.Approved
NevirapineThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Nevirapine.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Diethylstilbestrol.Approved, Investigational
NitroaspirinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Nitroaspirin.Investigational
OleandrinOleandrin may decrease the cardiotoxic activities of Diethylstilbestrol.Experimental, Investigational
Oleoyl-estroneThe serum concentration of Oleoyl-estrone can be increased when it is combined with Diethylstilbestrol.Investigational
OmapatrilatThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Omapatrilat.Investigational
OspemifeneThe risk or severity of adverse effects can be increased when Diethylstilbestrol is combined with Ospemifene.Approved
OtamixabanThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Otamixaban.Investigational
OuabainOuabain may decrease the cardiotoxic activities of Diethylstilbestrol.Approved
OxcarbazepineThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Oxcarbazepine.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Diethylstilbestrol.Approved, Vet Approved
ParamethasoneThe serum concentration of Paramethasone can be increased when it is combined with Diethylstilbestrol.Approved
ParecoxibParecoxib may increase the thrombogenic activities of Diethylstilbestrol.Approved
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Diethylstilbestrol.Approved
Pentaerythritol TetranitrateDiethylstilbestrol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
PentobarbitalThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateDiethylstilbestrol may decrease the anticoagulant activities of Pentosan Polysulfate.Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Diethylstilbestrol.Approved, Investigational, Vet Approved, Withdrawn
PerindoprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Perindopril.Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Diethylstilbestrol.Experimental
PhenindioneDiethylstilbestrol may decrease the anticoagulant activities of Phenindione.Approved, Investigational
PhenobarbitalThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Phenobarbital.Approved
PhenprocoumonDiethylstilbestrol may decrease the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhenytoinThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Phenytoin.Approved, Vet Approved
PhosphoramidonThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Phosphoramidon.Experimental
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Diethylstilbestrol.Approved
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Diethylstilbestrol.Approved, Nutraceutical
Prasterone sulfateThe serum concentration of Prasterone sulfate can be increased when it is combined with Diethylstilbestrol.Investigational
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Diethylstilbestrol.Approved
PrednicarbateThe serum concentration of Prednicarbate can be increased when it is combined with Diethylstilbestrol.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Diethylstilbestrol.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Diethylstilbestrol.Approved, Vet Approved
PregnenoloneThe serum concentration of Pregnenolone can be increased when it is combined with Diethylstilbestrol.Experimental, Investigational
PrimidoneThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Primidone.Approved, Vet Approved
PrinomastatThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Prinomastat.Investigational
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Diethylstilbestrol.Experimental
Protein CDiethylstilbestrol may decrease the anticoagulant activities of Protein C.Approved
Protein S humanDiethylstilbestrol may decrease the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeDiethylstilbestrol may decrease the anticoagulant activities of Protocatechualdehyde.Approved
PrucaloprideThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Prucalopride.Approved
QuinaprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Quinapril.Approved, Investigational
RacecadotrilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Racecadotril.Investigational
RamiprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Ramipril.Approved
RanolazineThe serum concentration of Diethylstilbestrol can be increased when it is combined with Ranolazine.Approved, Investigational
RemikirenThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Remikiren.Approved
ReviparinDiethylstilbestrol may decrease the anticoagulant activities of Reviparin.Approved, Investigational
RifabutinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Rifapentine.Approved
RifaximinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Rifaximin.Approved, Investigational
RimexoloneThe serum concentration of Rimexolone can be increased when it is combined with Diethylstilbestrol.Approved
RitonavirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Rivaroxaban.Approved
RofecoxibRofecoxib may increase the thrombogenic activities of Diethylstilbestrol.Investigational, Withdrawn
RopiniroleThe serum concentration of Ropinirole can be increased when it is combined with Diethylstilbestrol.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Diethylstilbestrol.Approved
S-3304The serum concentration of Diethylstilbestrol can be decreased when it is combined with S-3304.Investigational
SaquinavirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Saxagliptin.Approved
SecobarbitalThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Secobarbital.Approved, Vet Approved
SelegilineThe serum concentration of Selegiline can be increased when it is combined with Diethylstilbestrol.Approved, Investigational, Vet Approved
SimeprevirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Diethylstilbestrol.Approved
SitagliptinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Sitagliptin.Approved, Investigational
SivelestatThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Sivelestat.Investigational
SomatotropinThe therapeutic efficacy of Somatotropin can be decreased when used in combination with Diethylstilbestrol.Approved, Investigational
SpiraprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Spirapril.Approved
St. John's WortThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with St. John's Wort.Investigational, Nutraceutical
SulodexideDiethylstilbestrol may decrease the anticoagulant activities of Sulodexide.Approved, Investigational
TelaprevirThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Telaprevir.Approved, Withdrawn
TemocaprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Temocapril.Experimental, Investigational
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Diethylstilbestrol.Experimental
Testosterone PropionateThe metabolism of Diethylstilbestrol can be decreased when combined with Testosterone Propionate.Approved, Vet Approved
ThalidomideDiethylstilbestrol may increase the thrombogenic activities of Thalidomide.Approved, Investigational, Withdrawn
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Diethylstilbestrol.Approved
ThiamylalThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Thiamylal.Approved, Vet Approved
ThiopentalThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Thiopental.Approved, Vet Approved
ThiorphanThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Thiorphan.Experimental
Thyroid, porcineThe therapeutic efficacy of Thyroid, porcine can be decreased when used in combination with Diethylstilbestrol.Approved
TioclomarolDiethylstilbestrol may decrease the anticoagulant activities of Tioclomarol.Experimental
TipranavirDiethylstilbestrol may increase the dermatologic adverse activities of Tipranavir.Approved, Investigational
TixocortolThe serum concentration of Tixocortol can be increased when it is combined with Diethylstilbestrol.Approved
TolcaponeThe metabolism of Diethylstilbestrol can be decreased when combined with Tolcapone.Approved, Withdrawn
TopiramateThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Topiramate.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Diethylstilbestrol.Approved, Investigational
TrandolaprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Trandolapril.Approved
Tranexamic AcidDiethylstilbestrol may increase the thrombogenic activities of Tranexamic Acid.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Diethylstilbestrol.Approved, Investigational
TretinoinThe therapeutic efficacy of Diethylstilbestrol can be decreased when used in combination with Tretinoin.Approved, Investigational, Nutraceutical
TriamcinoloneThe serum concentration of Triamcinolone can be increased when it is combined with Diethylstilbestrol.Approved, Vet Approved
TroxerutinDiethylstilbestrol may decrease the anticoagulant activities of Troxerutin.Investigational
UbenimexThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Ubenimex.Experimental, Investigational
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Diethylstilbestrol.Approved, Investigational, Nutraceutical
UlinastatinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Ulinastatin.Investigational
UlobetasolThe serum concentration of Ulobetasol can be increased when it is combined with Diethylstilbestrol.Approved
Ursodeoxycholic acidThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Diethylstilbestrol.Approved, Investigational
ValdecoxibValdecoxib may increase the thrombogenic activities of Diethylstilbestrol.Investigational, Withdrawn
VildagliptinThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Vildagliptin.Approved, Investigational
Vitamin CThe serum concentration of Diethylstilbestrol can be increased when it is combined with Vitamin C.Approved, Nutraceutical
VoriconazoleThe metabolism of Diethylstilbestrol can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinDiethylstilbestrol may decrease the anticoagulant activities of Warfarin.Approved
XimelagatranThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
Z-Val-Ala-Asp fluoromethyl ketoneThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Z-Val-Ala-Asp fluoromethyl ketone.Experimental
ZofenoprilThe serum concentration of Diethylstilbestrol can be decreased when it is combined with Zofenopril.Experimental
Food Interactions
Not Available

References

Synthesis Reference

Adler, E.,Gie, G.J. and von Euler, H.; US. Patent 2,421,401; June 3, 1947; assigned to Hoffmann-La Roche, Inc.

General References
  1. Authors unspecified: Leuprolide versus diethylstilbestrol for metastatic prostate cancer. The Leuprolide Study Group. N Engl J Med. 1984 Nov 15;311(20):1281-6. [PubMed:6436700]
  2. DIECKMANN WJ, DAVIS ME, RYNKIEWICZ LM, POTTINGER RE: Does the administration of diethylstilbestrol during pregnancy have therapeutic value? Am J Obstet Gynecol. 1953 Nov;66(5):1062-81. [PubMed:13104505]
  3. Ingle JN, Ahmann DL, Green SJ, Edmonson JH, Bisel HF, Kvols LK, Nichols WC, Creagan ET, Hahn RG, Rubin J, Frytak S: Randomized clinical trial of diethylstilbestrol versus tamoxifen in postmenopausal women with advanced breast cancer. N Engl J Med. 1981 Jan 1;304(1):16-21. [PubMed:7001242]
  4. Kuchera LK: Postcoital contraception with diethylstilbestrol. JAMA. 1971 Oct 25;218(4):562-3. [PubMed:5171004]
  5. Herbst AL, Ulfelder H, Poskanzer DC: Adenocarcinoma of the vagina. Association of maternal stilbestrol therapy with tumor appearance in young women. N Engl J Med. 1971 Apr 15;284(15):878-81. [PubMed:5549830]
External Links
KEGG Drug
D00577
KEGG Compound
C07620
PubChem Compound
3054
PubChem Substance
46507453
ChemSpider
395306
BindingDB
20625
ChEBI
41922
ChEMBL
CHEMBL411
Therapeutic Targets Database
DAP001011
PharmGKB
PA449307
HET
DES
Wikipedia
Diethylstilbestrol
ATC Codes
L02AA01 — DiethylstilbestrolG03CC05 — DiethylstilbestrolG03CB02 — DiethylstilbestrolL02AA04 — Fosfestrol
PDB Entries
1s9p / 1tt6 / 1tz8 / 3erd / 4zn7
MSDS
Download (73.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentProstate Cancer1
3CompletedPreventionOrthopedic Disorders1
3CompletedTreatmentProstate Cancer1
3RecruitingPreventionAnaesthesia therapy2
3RecruitingPreventionAdjunct to general anesthesia therapy1
4RecruitingDiagnosticAnesthesia; Adverse Effect / Laryngeal Masks / Respiratory System Abnormalities1
Not AvailableCompletedPreventionIschemia, Cerebral1

Pharmacoeconomics

Manufacturers
  • Bristol myers squibb
  • Eli lilly and co
  • Tablicaps inc
  • Bayer pharmaceuticals corp
Packagers
Dosage forms
FormRouteStrength
LiquidIntravenous250 mg
TabletOral100 mg
TabletOral1 mg
TabletOral0.105 mg
TabletOral0.51 mg
TabletOral1.0 mg
TabletOral.1 mg
TabletOral.5 mg
Prices
Unit descriptionCostUnit
Diethylstilbestrol powder13.77USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)172Adler, E.,Gie, G.J. and von Euler, H.; US. Patent 2,421,401; June 3, 1947; assigned to Hoffmann-La Roche, Inc.
water solubility12 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP5.07HANSCH,C ET AL. (1995)
logS-4.35ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0109 mg/mLALOGPS
logP4.62ALOGPS
logP5.19ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.13ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity83.24 m3·mol-1ChemAxon
Polarizability30.69 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9973
Blood Brain Barrier-0.5559
Caco-2 permeable+0.8264
P-glycoprotein substrateSubstrate0.5737
P-glycoprotein inhibitor INon-inhibitor0.6542
P-glycoprotein inhibitor IINon-inhibitor0.8478
Renal organic cation transporterNon-inhibitor0.8465
CYP450 2C9 substrateNon-substrate0.8149
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.5107
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorInhibitor0.9064
CYP450 2D6 inhibitorNon-inhibitor0.7017
CYP450 2C19 inhibitorInhibitor0.9198
CYP450 3A4 inhibitorInhibitor0.8361
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9488
Ames testNon AMES toxic0.9579
CarcinogenicityNon-carcinogens0.6772
BiodegradationNot ready biodegradable0.9111
Rat acute toxicity1.9462 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6894
hERG inhibition (predictor II)Non-inhibitor0.6408
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.87 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Stilbenes
Sub Class
Not Available
Direct Parent
Stilbenes
Alternative Parents
Phenylpropanes / 1-hydroxy-2-unsubstituted benzenoids / Organooxygen compounds / Hydrocarbon derivatives
Substituents
Stilbene / Phenylpropane / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Benzenoid / Monocyclic benzene moiety / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Aromatic homomonocyclic compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. Estrogen receptor alpha
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Munoz G, Ovilo C, Estelle J, Silio L, Fernandez A, Rodriguez C: Association with litter size of new polymorphisms on ESR1 and ESR2 genes in a Chinese-European pig line. Genet Sel Evol. 2007 Mar-Apr;39(2):195-206. Epub 2007 Feb 17. [PubMed:17306201]
  2. Dixon A, Wells CC, Singh S, Babayan R, Maric C: Renoprotective effects of a selective estrogen receptor modulator, raloxifene, in an animal model of diabetic nephropathy. Am J Nephrol. 2007;27(2):120-8. Epub 2007 Feb 15. [PubMed:17308373]
  3. Hart SA, Snyder MA, Smejkalova T, Woolley CS: Estrogen mobilizes a subset of estrogen receptor-alpha-immunoreactive vesicles in inhibitory presynaptic boutons in hippocampal CA1. J Neurosci. 2007 Feb 21;27(8):2102-11. [PubMed:17314305]
  4. Baron S, Escande A, Alberola G, Bystricky K, Balaguer P, Richard-Foy H: Estrogen receptor alpha and the activating protein-1 complex cooperate during insulin-like growth factor-I-induced transcriptional activation of the pS2/TFF1 gene. J Biol Chem. 2007 Apr 20;282(16):11732-41. Epub 2007 Feb 22. [PubMed:17317669]
  5. Bains M, Cousins JC, Roberts JL: Neuroprotection by estrogen against MPP+-induced dopamine neuron death is mediated by ERalpha in primary cultures of mouse mesencephalon. Exp Neurol. 2007 Apr;204(2):767-76. Epub 2007 Jan 25. [PubMed:17320868]
  6. Kwok KC, Cheung NH: Measuring binding kinetics of ligands with tethered receptors by fluorescence polarization and total internal reflection fluorescence. Anal Chem. 2010 May 1;82(9):3819-25. doi: 10.1021/ac1002245. [PubMed:20387803]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Orphan receptor that acts as transcription activator in the absence of bound ligand. Binds specifically to an estrogen response element and activates reporter genes controlled by estrogen response ...
Gene Name
ESRRG
Uniprot ID
P62508
Uniprot Name
Estrogen-related receptor gamma
Molecular Weight
51305.485 Da
References
  1. Greschik H, Flaig R, Renaud JP, Moras D: Structural basis for the deactivation of the estrogen-related receptor gamma by diethylstilbestrol or 4-hydroxytamoxifen and determinants of selectivity. J Biol Chem. 2004 Aug 6;279(32):33639-46. Epub 2004 May 24. [PubMed:15161930]
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
  3. Tremblay GB, Kunath T, Bergeron D, Lapointe L, Champigny C, Bader JA, Rossant J, Giguere V: Diethylstilbestrol regulates trophoblast stem cell differentiation as a ligand of orphan nuclear receptor ERR beta. Genes Dev. 2001 Apr 1;15(7):833-8. [PubMed:11297507]
Details
3. Estrogen receptor beta
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
Gene Name
ESR2
Uniprot ID
Q92731
Uniprot Name
Estrogen receptor beta
Molecular Weight
59215.765 Da
References
  1. Authors unspecified: Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products. Int J Toxicol. 2008;27 Suppl 4:1-82. doi: 10.1080/10915810802548359. [PubMed:19101832]
  2. Geistlinger TR, McReynolds AC, Guy RK: Ligand-selective inhibition of the interaction of steroid receptor coactivators and estrogen receptor isoforms. Chem Biol. 2004 Feb;11(2):273-81. [PubMed:15123288]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Binds to an ERR-alpha response element (ERRE) containing a single consensus half-site, 5'-TNAAGGTCA-3'. Can bind to the medium-chain acyl coenzyme A dehydrogenase (MCAD) response element NRRE-1 and...
Gene Name
ESRRA
Uniprot ID
P11474
Uniprot Name
Steroid hormone receptor ERR1
Molecular Weight
45509.11 Da
References
  1. Tremblay GB, Kunath T, Bergeron D, Lapointe L, Champigny C, Bader JA, Rossant J, Giguere V: Diethylstilbestrol regulates trophoblast stem cell differentiation as a ligand of orphan nuclear receptor ERR beta. Genes Dev. 2001 Apr 1;15(7):833-8. [PubMed:11297507]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor, may regulate ESR1 transcriptional activity. Induces the expression of PERM1 in the skeletal muscle.
Gene Name
ESRRB
Uniprot ID
O95718
Uniprot Name
Steroid hormone receptor ERR2
Molecular Weight
56207.085 Da
References
  1. Tremblay GB, Kunath T, Bergeron D, Lapointe L, Champigny C, Bader JA, Rossant J, Giguere V: Diethylstilbestrol regulates trophoblast stem cell differentiation as a ligand of orphan nuclear receptor ERR beta. Genes Dev. 2001 Apr 1;15(7):833-8. [PubMed:11297507]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Transcription coactivator activity
Specific Function
Transcriptional coactivator for steroid receptors and nuclear receptors. Coactivator of the steroid binding domain (AF-2) but not of the modulating N-terminal domain (AF-1). Required with NCOA1 to ...
Gene Name
NCOA2
Uniprot ID
Q15596
Uniprot Name
Nuclear receptor coactivator 2
Molecular Weight
159155.645 Da
References
  1. Geistlinger TR, McReynolds AC, Guy RK: Ligand-selective inhibition of the interaction of steroid receptor coactivators and estrogen receptor isoforms. Chem Biol. 2004 Feb;11(2):273-81. [PubMed:15123288]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Kretschmer XC, Baldwin WS: CAR and PXR: xenosensors of endocrine disrupters? Chem Biol Interact. 2005 Aug 15;155(3):111-28. [PubMed:16054614]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Tamura H, Ishimoto Y, Fujikawa T, Aoyama H, Yoshikawa H, Akamatsu M: Structural basis for androgen receptor agonists and antagonists: interaction of SPEED 98-listed chemicals and related compounds with the androgen receptor based on an in vitro reporter gene assay and 3D-QSAR. Bioorg Med Chem. 2006 Nov 1;14(21):7160-74. Epub 2006 Jul 28. [PubMed:16876421]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [PubMed:25349334]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
O-methyltransferase activity
Specific Function
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOP...
Gene Name
COMT
Uniprot ID
P21964
Uniprot Name
Catechol O-methyltransferase
Molecular Weight
30036.77 Da
References
  1. Engel LL, Weidenfield J, Merriam GR: Metabolism of diethylstilbestrol by rat liver: a preliminary report. J Toxicol Environ Health Suppl. 1976;1:37-44. [PubMed:11352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Qu YQ, Fang ZZ, Yang L, Gao ZM, Liang R, Zhu LL, Dong PP, Zhang YY, Ge GB, Wang LM: Reversible inhibition of four important human liver cytochrome P450 enzymes by diethylstilbestrol. Pharmazie. 2011 Mar;66(3):216-21. [PubMed:21553654]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Qu YQ, Fang ZZ, Yang L, Gao ZM, Liang R, Zhu LL, Dong PP, Zhang YY, Ge GB, Wang LM: Reversible inhibition of four important human liver cytochrome P450 enzymes by diethylstilbestrol. Pharmazie. 2011 Mar;66(3):216-21. [PubMed:21553654]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Qu YQ, Fang ZZ, Yang L, Gao ZM, Liang R, Zhu LL, Dong PP, Zhang YY, Ge GB, Wang LM: Reversible inhibition of four important human liver cytochrome P450 enzymes by diethylstilbestrol. Pharmazie. 2011 Mar;66(3):216-21. [PubMed:21553654]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Qu YQ, Fang ZZ, Yang L, Gao ZM, Liang R, Zhu LL, Dong PP, Zhang YY, Ge GB, Wang LM: Reversible inhibition of four important human liver cytochrome P450 enzymes by diethylstilbestrol. Pharmazie. 2011 Mar;66(3):216-21. [PubMed:21553654]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Qu YQ, Fang ZZ, Yang L, Gao ZM, Liang R, Zhu LL, Dong PP, Zhang YY, Ge GB, Wang LM: Reversible inhibition of four important human liver cytochrome P450 enzymes by diethylstilbestrol. Pharmazie. 2011 Mar;66(3):216-21. [PubMed:21553654]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Identical protein binding
Specific Function
Thyroid hormone-binding protein. Probably transports thyroxine from the bloodstream to the brain.
Gene Name
TTR
Uniprot ID
P02766
Uniprot Name
Transthyretin
Molecular Weight
15886.88 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Sugimoto Y, Tsukahara S, Imai Y, Sugimoto Y, Ueda K, Tsuruo T: Reversal of breast cancer resistance protein-mediated drug resistance by estrogen antagonists and agonists. Mol Cancer Ther. 2003 Jan;2(1):105-12. [PubMed:12533678]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Rao US, Fine RL, Scarborough GA: Antiestrogens and steroid hormones: substrates of the human P-glycoprotein. Biochem Pharmacol. 1994 Jul 19;48(2):287-92. [PubMed:7914405]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 17:23