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Identification
NameDienestrol
Accession NumberDB00890  (APRD00917)
TypeSmall Molecule
GroupsApproved
DescriptionDienestrol is a synthetic, non-steroidal estrogen. It is an estrogen receptor agonist. Estrogens work partly by increasing a normal clear discharge from the vagina and making the vulva and urethra healthy. Using or applying an estrogen relieves or lessens: dryness and soreness in the vagina, itching, redness, or soreness of the vulva. Conditions that are treated with vaginal estrogens include a genital skin condition (vulvar atrophy), inflammation of the vagina (atrophic vaginitis), and inflammation of the urethra (atrophic urethritis).
Structure
Thumb
Synonyms
alpha-dienestrol diacetate
Cycladiene
Dehydrostilbestrol
Dienestrol
Diènestrol
Dienestrol
Dienestrolum
DV
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ortho Dienestrol CrmCream.01 %VaginalOrtho Pharmaceutical, Division Of Janssen Ortho Inc.1951-12-312002-08-02Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EstraguardNot Available
EstraguardNot Available
EstroralNot Available
Ortho DienestrolOrtho-McNeil Pharmaceutical
RestrolNot Available
RetalonNot Available
SexadienLEO Pharma A/S
SynestrolNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIRRW32X4U1F
CAS number13029-44-2
WeightAverage: 266.3343
Monoisotopic: 266.13067982
Chemical FormulaC18H18O2
InChI KeyNFDFQCUYFHCNBW-SCGPFSFSSA-N
InChI
InChI=1S/C18H18O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h3-12,19-20H,1-2H3/b17-3+,18-4+
IUPAC Name
4-[4-(4-hydroxyphenyl)hexa-2,4-dien-3-yl]phenol
SMILES
CC=C(C(=CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
Pharmacology
IndicationFor use in the treatment of atrophic vaginitis and kraurosis vulvae.
Structured Indications Not Available
PharmacodynamicsEstrogens 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).
Mechanism of actionDienestrol is a synthetic, non-steroidal estrogen. Estrogens passively diffuse into target cells of responsive tissues, complex with the estrogen receptors, and enter the cell's nucleus to initiate or enhance gene transcription of protein synthesis after binding to DNA.
TargetKindPharmacological actionActionsOrganismUniProt ID
Estrogen receptorProteinyes
agonist
HumanP03372 details
Related Articles
AbsorptionSystemic absorption and mode of action of dienestrol are undetermined.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).
Volume of distributionNot Available
Protein binding50 to 80%
Metabolism

Hepatic.

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySymptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe serum concentration of Dienestrol 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 Dienestrol.Investigational
19-norandrostenedioneThe serum concentration of 19-norandrostenedione can be increased when it is combined with Dienestrol.Experimental, Illicit
3,4-DichloroisocoumarinThe serum concentration of Dienestrol can be decreased when it is combined with 3,4-Dichloroisocoumarin.Experimental
4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDEThe serum concentration of Dienestrol can be decreased when it is combined with 4-(2-AMINOETHYL)BENZENESULFONYL FLUORIDE.Experimental
4-AndrostenedioneThe serum concentration of 4-Androstenedione can be increased when it is combined with Dienestrol.Experimental, Illicit
5-androstenedioneThe serum concentration of 5-androstenedione can be increased when it is combined with Dienestrol.Experimental, Illicit
AbciximabDienestrol may decrease the anticoagulant activities of Abciximab.Approved
AcenocoumarolDienestrol may decrease the anticoagulant activities of Acenocoumarol.Approved
AcitretinThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Acitretin.Approved
AdapaleneThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Adapalene.Approved
AlclometasoneThe serum concentration of Alclometasone can be increased when it is combined with Dienestrol.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Dienestrol.Experimental
AlitretinoinThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Alitretinoin.Approved, Investigational
AlogliptinThe serum concentration of Dienestrol can be decreased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Dienestrol 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 Dienestrol.Experimental
AmcinonideThe serum concentration of Amcinonide can be increased when it is combined with Dienestrol.Approved
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Dienestrol.Approved
AmobarbitalThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Amobarbital.Approved, Illicit
AmprenavirThe serum concentration of Dienestrol can be decreased when it is combined with Amprenavir.Approved
AnastrozoleThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Dienestrol.Approved, Investigational
AncrodDienestrol may decrease the anticoagulant activities of Ancrod.Investigational
AnecortaveThe serum concentration of Anecortave can be increased when it is combined with Dienestrol.Investigational
Anthrax immune globulin humanDienestrol may increase the thrombogenic activities of Anthrax immune globulin human.Approved
Antithrombin III humanThe serum concentration of Dienestrol can be decreased when it is combined with Antithrombin III human.Approved
ApixabanThe serum concentration of Dienestrol can be decreased when it is combined with Apixaban.Approved
AprepitantThe serum concentration of Dienestrol can be decreased when it is combined with Aprepitant.Approved, Investigational
AprotininThe serum concentration of Dienestrol can be decreased when it is combined with Aprotinin.Approved, Withdrawn
ArdeparinDienestrol may decrease the anticoagulant activities of Ardeparin.Approved, Withdrawn
ArgatrobanThe serum concentration of Dienestrol can be decreased when it is combined with Argatroban.Approved, Investigational
ArmodafinilThe serum concentration of Dienestrol can be decreased when it is combined with Armodafinil.Approved, Investigational
ArtemetherThe serum concentration of Dienestrol can be decreased when it is combined with Artemether.Approved
AsunaprevirThe serum concentration of Dienestrol can be decreased when it is combined with Asunaprevir.Approved, Investigational
AtazanavirThe serum concentration of Dienestrol can be decreased when it is combined with Atazanavir.Approved, Investigational
BarbexacloneThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Barbexaclone.Experimental
BarbitalThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Barbital.Illicit
BatimastatThe serum concentration of Dienestrol can be decreased when it is combined with Batimastat.Experimental
BecaplerminDienestrol may decrease the anticoagulant activities of Becaplermin.Approved, Investigational
BeclomethasoneThe serum concentration of Beclomethasone can be increased when it is combined with Dienestrol.Investigational
Beclomethasone dipropionateThe serum concentration of Beclomethasone dipropionate can be increased when it is combined with Dienestrol.Approved, Investigational
BenazeprilThe serum concentration of Dienestrol can be decreased when it is combined with Benazepril.Approved, Investigational
BenzamidineThe serum concentration of Dienestrol can be decreased when it is combined with Benzamidine.Experimental
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Dienestrol.Approved, Vet Approved
BexaroteneThe serum concentration of Dienestrol can be decreased when it is combined with Bexarotene.Approved, Investigational
BexaroteneThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Bexarotene.Approved, Investigational
Bi201335The serum concentration of Dienestrol can be decreased when it is combined with Bi201335.Investigational
BivalirudinThe serum concentration of Dienestrol can be decreased when it is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Dienestrol can be decreased when it is combined with Boceprevir.Approved
BosentanThe serum concentration of Dienestrol can be decreased when it is combined with Bosentan.Approved, Investigational
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Dienestrol.Approved
C1 Esterase Inhibitor (Human)Dienestrol may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).Approved
C1 Esterase Inhibitor (Recombinant)Dienestrol may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).Approved
CandoxatrilThe serum concentration of Dienestrol can be decreased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Dienestrol can be decreased when it is combined with Candoxatrilat.Experimental
CaptoprilThe serum concentration of Dienestrol can be decreased when it is combined with Captopril.Approved
CarbamazepineThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Carbamazepine.Approved, Investigational
CelecoxibCelecoxib may increase the thrombogenic activities of Dienestrol.Approved, Investigational
CertoparinDienestrol may decrease the anticoagulant activities of Certoparin.Approved
Chenodeoxycholic acidThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Dienestrol.Approved
CholestyramineThe serum concentration of Dienestrol can be decreased when it is combined with Cholestyramine.Approved
ChymostatinThe serum concentration of Dienestrol can be decreased when it is combined with Chymostatin.Experimental
CiclesonideThe serum concentration of Ciclesonide can be increased when it is combined with Dienestrol.Approved, Investigational
CilastatinThe serum concentration of Dienestrol can be decreased when it is combined with Cilastatin.Approved
CilazaprilThe serum concentration of Dienestrol can be decreased when it is combined with Cilazapril.Approved
Citric AcidDienestrol may decrease the anticoagulant activities of Citric Acid.Nutraceutical, Vet Approved
ClobazamThe serum concentration of Dienestrol can be decreased when it is combined with Clobazam.Approved, Illicit
ClobetasolThe serum concentration of Clobetasol can be increased when it is combined with Dienestrol.Investigational
Clobetasol propionateThe serum concentration of Clobetasol propionate can be increased when it is combined with Dienestrol.Approved
ClocortoloneThe serum concentration of Clocortolone can be increased when it is combined with Dienestrol.Approved
CobicistatThe serum concentration of Dienestrol can be decreased when it is combined with Cobicistat.Approved
ColesevelamThe serum concentration of Dienestrol can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Dienestrol can be decreased when it is combined with Colestipol.Approved
Cortisone acetateThe serum concentration of Cortisone acetate can be increased when it is combined with Dienestrol.Approved
Dabigatran etexilateThe serum concentration of Dienestrol can be decreased when it is combined with Dabigatran etexilate.Approved
DabrafenibThe serum concentration of Dienestrol can be decreased when it is combined with Dabrafenib.Approved
DalteparinDienestrol may decrease the anticoagulant activities of Dalteparin.Approved
DanaparoidDienestrol may decrease the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarunavirThe serum concentration of Dienestrol can be decreased when it is combined with Darunavir.Approved
dehydroepiandrosterone sulfateThe serum concentration of dehydroepiandrosterone sulfate can be increased when it is combined with Dienestrol.Investigational
DesirudinDienestrol may decrease the anticoagulant activities of Desirudin.Approved
DesoximetasoneThe serum concentration of Desoximetasone can be increased when it is combined with Dienestrol.Approved
Desoxycorticosterone acetateThe serum concentration of Desoxycorticosterone acetate can be increased when it is combined with Dienestrol.Approved
Desoxycorticosterone PivalateThe serum concentration of Desoxycorticosterone Pivalate can be increased when it is combined with Dienestrol.Experimental, Vet Approved
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Dienestrol.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe serum concentration of Dexamethasone isonicotinate can be increased when it is combined with Dienestrol.Vet Approved
DextranDienestrol may decrease the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Dienestrol may decrease the anticoagulant activities of Dextran 40.Approved
Dextran 70Dienestrol may decrease the anticoagulant activities of Dextran 70.Approved
Dextran 75Dienestrol may decrease the anticoagulant activities of Dextran 75.Approved
DicoumarolDienestrol may decrease the anticoagulant activities of Dicoumarol.Approved
DiflorasoneThe serum concentration of Diflorasone can be increased when it is combined with Dienestrol.Approved
DifluocortoloneThe serum concentration of Difluocortolone can be increased when it is combined with Dienestrol.Approved
DifluprednateThe serum concentration of Difluprednate can be increased when it is combined with Dienestrol.Approved
DyphyllineThe serum concentration of Dyphylline can be increased when it is combined with Dienestrol.Approved
EcabetThe serum concentration of Dienestrol can be decreased when it is combined with Ecabet.Approved, Investigational
Edetic AcidDienestrol may decrease the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanThe serum concentration of Dienestrol can be decreased when it is combined with Edoxaban.Approved
ElafinThe serum concentration of Dienestrol can be decreased when it is combined with Elafin.Investigational
ElvitegravirThe serum concentration of Dienestrol can be decreased when it is combined with Elvitegravir.Approved
EnalaprilThe serum concentration of Dienestrol can be decreased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Dienestrol can be decreased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Dienestrol can be decreased when it is combined with Enalkiren.Experimental
EnoxaparinDienestrol may decrease the anticoagulant activities of Enoxaparin.Approved
EquileninThe serum concentration of Equilenin can be increased when it is combined with Dienestrol.Experimental
EquilinThe serum concentration of Equilin can be increased when it is combined with Dienestrol.Approved
Eslicarbazepine acetateThe serum concentration of Dienestrol can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Dienestrol.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be increased when it is combined with Dienestrol.Approved
Ethyl biscoumacetateDienestrol may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacEtodolac may increase the thrombogenic activities of Dienestrol.Approved, Investigational, Vet Approved
EtoricoxibEtoricoxib may increase the thrombogenic activities of Dienestrol.Approved, Investigational
ExemestaneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Dienestrol.Approved, Investigational
ExenatideThe serum concentration of Dienestrol can be decreased when it is combined with Exenatide.Approved, Investigational
FelbamateThe serum concentration of Dienestrol can be decreased when it is combined with Felbamate.Approved
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Dienestrol.Approved
fluasteroneThe serum concentration of fluasterone can be increased when it is combined with Dienestrol.Investigational
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Dienestrol.Approved
FluindioneDienestrol may decrease the anticoagulant activities of Fluindione.Investigational
FlumethasoneThe serum concentration of Flumethasone can be increased when it is combined with Dienestrol.Approved, Vet Approved
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Dienestrol.Approved, Investigational
Fluocinolone AcetonideThe serum concentration of Fluocinolone Acetonide can be increased when it is combined with Dienestrol.Approved, Investigational, Vet Approved
FluocinonideThe serum concentration of Fluocinonide can be increased when it is combined with Dienestrol.Approved, Investigational
FluocortoloneThe serum concentration of Fluocortolone can be increased when it is combined with Dienestrol.Approved, Withdrawn
FluorometholoneThe serum concentration of Fluorometholone can be increased when it is combined with Dienestrol.Approved
FluprednideneThe serum concentration of Fluprednidene can be increased when it is combined with Dienestrol.Approved, Withdrawn
FluprednisoloneThe serum concentration of Fluprednisolone can be increased when it is combined with Dienestrol.Approved
FlurandrenolideThe serum concentration of Flurandrenolide can be increased when it is combined with Dienestrol.Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Dienestrol.Approved
Fluticasone PropionateThe serum concentration of Fluticasone Propionate can be increased when it is combined with Dienestrol.Approved
FondaparinuxDienestrol may decrease the anticoagulant activities of Fondaparinux.Investigational
Fondaparinux sodiumDienestrol may decrease the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
FormestaneThe serum concentration of Formestane can be increased when it is combined with Dienestrol.Approved, Investigational, Withdrawn
FosamprenavirThe serum concentration of Dienestrol can be decreased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Dienestrol can be decreased when it is combined with Fosaprepitant.Approved
FosinoprilThe serum concentration of Dienestrol can be decreased when it is combined with Fosinopril.Approved
FosphenytoinThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Fosphenytoin.Approved
GabexateThe serum concentration of Dienestrol can be decreased when it is combined with Gabexate.Investigational
GeldanamycinThe serum concentration of Dienestrol can be decreased when it is combined with Geldanamycin.Experimental
GM6001The serum concentration of Dienestrol can be decreased when it is combined with GM6001.Experimental
GriseofulvinThe metabolism of Dienestrol can be increased when combined with Griseofulvin.Approved, Vet Approved
HE3286The serum concentration of HE3286 can be increased when it is combined with Dienestrol.Investigational
HeparinDienestrol may decrease the anticoagulant activities of Heparin.Approved, Investigational
HexobarbitalThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Hexobarbital.Approved
HirulogThe serum concentration of Dienestrol can be decreased when it is combined with Hirulog.Experimental
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Dienestrol.Approved, Investigational
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Dienestrol.Approved, Vet Approved
idraparinuxThe serum concentration of Dienestrol can be decreased when it is combined with idraparinux.Investigational
ImidaprilThe serum concentration of Dienestrol can be decreased when it is combined with Imidapril.Investigational
IndinavirThe serum concentration of Dienestrol can be decreased when it is combined with Indinavir.Approved
IsoflurophateThe serum concentration of Dienestrol can be decreased when it is combined with Isoflurophate.Approved, Withdrawn
IsotretinoinThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Isotretinoin.Approved
IstaroximeThe serum concentration of Istaroxime can be increased when it is combined with Dienestrol.Investigational
IxazomibThe serum concentration of Dienestrol can be decreased when it is combined with Ixazomib.Approved
LamotrigineThe serum concentration of Lamotrigine can be decreased when it is combined with Dienestrol.Approved, Investigational
LenalidomideDienestrol may increase the thrombogenic activities of Lenalidomide.Approved
LepirudinThe serum concentration of Dienestrol can be decreased when it is combined with Lepirudin.Approved
LevothyroxineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Dienestrol.Approved
LinagliptinThe serum concentration of Dienestrol can be decreased when it is combined with Linagliptin.Approved
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Dienestrol.Approved, Vet Approved
LiotrixThe therapeutic efficacy of Liotrix can be decreased when used in combination with Dienestrol.Approved
LisinoprilThe serum concentration of Dienestrol can be decreased when it is combined with Lisinopril.Approved, Investigational
LopinavirThe serum concentration of Dienestrol can be decreased when it is combined with Lopinavir.Approved
LumacaftorThe serum concentration of Dienestrol can be decreased when it is combined with Lumacaftor.Approved
LumiracoxibLumiracoxib may increase the thrombogenic activities of Dienestrol.Approved, Investigational
ME-609The serum concentration of ME-609 can be increased when it is combined with Dienestrol.Investigational
MedrysoneThe serum concentration of Medrysone can be increased when it is combined with Dienestrol.Approved
MelengestrolThe serum concentration of Melengestrol can be increased when it is combined with Dienestrol.Vet Approved
MethohexitalThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Methohexital.Approved
MethylphenobarbitalThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Methylphenobarbital.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Dienestrol.Approved, Vet Approved
MetreleptinThe serum concentration of Dienestrol can be decreased when it is combined with Metreleptin.Approved
MifepristoneThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Mifepristone.Approved, Investigational
ModafinilThe serum concentration of Dienestrol can be decreased when it is combined with Modafinil.Approved, Investigational
MoexiprilThe serum concentration of Dienestrol can be decreased when it is combined with Moexipril.Approved
MometasoneThe serum concentration of Mometasone can be increased when it is combined with Dienestrol.Approved, Vet Approved
Mycophenolic acidThe serum concentration of Dienestrol can be decreased when it is combined with Mycophenolic acid.Approved
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Dienestrol can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NabumetoneNabumetone may increase the thrombogenic activities of Dienestrol.Approved
NadroparinDienestrol may decrease the anticoagulant activities of Nadroparin.Approved
NafamostatThe serum concentration of Dienestrol can be decreased when it is combined with Nafamostat.Investigational
NafcillinThe metabolism of Dienestrol can be increased when combined with Nafcillin.Approved
NCX 1022The serum concentration of NCX 1022 can be increased when it is combined with Dienestrol.Investigational
NCX 4016The serum concentration of Dienestrol can be decreased when it is combined with NCX 4016.Investigational
NelfinavirThe serum concentration of Dienestrol can be decreased when it is combined with Nelfinavir.Approved
NevirapineThe serum concentration of Dienestrol can be decreased when it is combined with Nevirapine.Approved
NitroaspirinThe serum concentration of Dienestrol can be decreased when it is combined with Nitroaspirin.Investigational
Oleoyl estroneThe serum concentration of Oleoyl estrone can be increased when it is combined with Dienestrol.Investigational
OmapatrilatThe serum concentration of Dienestrol can be decreased when it is combined with Omapatrilat.Investigational
OspemifeneThe risk or severity of adverse effects can be increased when Dienestrol is combined with Ospemifene.Approved
OtamixabanThe serum concentration of Dienestrol can be decreased when it is combined with Otamixaban.Investigational
OxcarbazepineThe serum concentration of Dienestrol can be decreased when it is combined with Oxcarbazepine.Approved
ParamethasoneThe serum concentration of Paramethasone can be increased when it is combined with Dienestrol.Approved
ParecoxibParecoxib may increase the thrombogenic activities of Dienestrol.Approved
PentobarbitalThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateDienestrol may decrease the anticoagulant activities of Pentosan Polysulfate.Approved
PerindoprilThe serum concentration of Dienestrol can be decreased when it is combined with Perindopril.Approved
PhenindioneDienestrol may decrease the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Phenobarbital.Approved
PhenprocoumonDienestrol may decrease the anticoagulant activities of Phenprocoumon.Approved
PhenytoinThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Phenytoin.Approved, Vet Approved
PhosphoramidonThe serum concentration of Dienestrol can be decreased when it is combined with Phosphoramidon.Experimental
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Dienestrol.Approved, Nutraceutical
PrednicarbateThe serum concentration of Prednicarbate can be increased when it is combined with Dienestrol.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Dienestrol.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Dienestrol.Approved, Vet Approved
PregnenoloneThe serum concentration of Pregnenolone can be increased when it is combined with Dienestrol.Experimental
PrimidoneThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Primidone.Approved, Vet Approved
PrinomastatThe serum concentration of Dienestrol can be decreased when it is combined with Prinomastat.Investigational
Protein CDienestrol may decrease the anticoagulant activities of Protein C.Approved
Protein S humanDienestrol may decrease the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeDienestrol may decrease the anticoagulant activities of Protocatechualdehyde.Approved
PrucaloprideThe serum concentration of Dienestrol can be decreased when it is combined with Prucalopride.Approved
QuinaprilThe serum concentration of Dienestrol can be decreased when it is combined with Quinapril.Approved, Investigational
RacecadotrilThe serum concentration of Dienestrol can be decreased when it is combined with Racecadotril.Investigational
RamiprilThe serum concentration of Dienestrol can be decreased when it is combined with Ramipril.Approved
RemikirenThe serum concentration of Dienestrol can be decreased when it is combined with Remikiren.Approved
ReviparinDienestrol may decrease the anticoagulant activities of Reviparin.Approved
RifabutinThe serum concentration of Dienestrol can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Dienestrol can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Dienestrol can be decreased when it is combined with Rifapentine.Approved
RimexoloneThe serum concentration of Rimexolone can be increased when it is combined with Dienestrol.Approved
RitonavirThe serum concentration of Dienestrol can be decreased when it is combined with Ritonavir.Approved, Investigational
RivaroxabanThe serum concentration of Dienestrol can be decreased when it is combined with Rivaroxaban.Approved
RofecoxibRofecoxib may increase the thrombogenic activities of Dienestrol.Investigational, Withdrawn
RopiniroleThe serum concentration of Ropinirole can be increased when it is combined with Dienestrol.Approved, Investigational
SaquinavirThe serum concentration of Dienestrol can be decreased when it is combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Dienestrol can be decreased when it is combined with Saxagliptin.Approved
SecobarbitalThe therapeutic efficacy of Dienestrol 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 Dienestrol.Approved, Investigational, Vet Approved
SimeprevirThe serum concentration of Dienestrol can be decreased when it is combined with Simeprevir.Approved
SitagliptinThe serum concentration of Dienestrol can be decreased when it is combined with Sitagliptin.Approved, Investigational
Somatropin recombinantThe therapeutic efficacy of Somatropin recombinant can be decreased when used in combination with Dienestrol.Approved, Investigational
SpiraprilThe serum concentration of Dienestrol can be decreased when it is combined with Spirapril.Approved
St. John's WortThe therapeutic efficacy of Dienestrol can be decreased when used in combination with St. John's Wort.Nutraceutical
SulodexideDienestrol may decrease the anticoagulant activities of Sulodexide.Approved, Investigational
TelaprevirThe serum concentration of Dienestrol can be decreased when it is combined with Telaprevir.Approved
TemocaprilThe serum concentration of Dienestrol can be decreased when it is combined with Temocapril.Experimental, Investigational
ThalidomideDienestrol may increase the thrombogenic activities of Thalidomide.Approved, Investigational, Withdrawn
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Dienestrol.Approved
ThiamylalThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Thiamylal.Approved, Vet Approved
ThiopentalThe therapeutic efficacy of Dienestrol can be decreased when used in combination with Thiopental.Approved, Vet Approved
ThiorphanThe serum concentration of Dienestrol 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 Dienestrol.Approved
TipranavirDienestrol may increase the dermatologic adverse activities of Tipranavir.Approved, Investigational
TixocortolThe serum concentration of Tixocortol can be increased when it is combined with Dienestrol.Approved
TopiramateThe serum concentration of Dienestrol can be decreased when it is combined with Topiramate.Approved
TrandolaprilThe serum concentration of Dienestrol can be decreased when it is combined with Trandolapril.Approved
Tranexamic AcidDienestrol may increase the thrombogenic activities of Tranexamic Acid.Approved
TretinoinThe therapeutic efficacy of Dienestrol 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 Dienestrol.Approved, Vet Approved
UbenimexThe serum concentration of Dienestrol can be decreased when it is combined with Ubenimex.Experimental
UlinastatinThe serum concentration of Dienestrol can be decreased when it is combined with Ulinastatin.Investigational
Ursodeoxycholic acidThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Dienestrol.Approved, Investigational
ValdecoxibValdecoxib may increase the thrombogenic activities of Dienestrol.Investigational, Withdrawn
VildagliptinThe serum concentration of Dienestrol can be decreased when it is combined with Vildagliptin.Approved, Investigational
Vitamin CThe serum concentration of Dienestrol can be increased when it is combined with Vitamin C.Approved, Nutraceutical
VoriconazoleThe metabolism of Dienestrol can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinDienestrol may decrease the anticoagulant activities of Warfarin.Approved
XimelagatranThe serum concentration of Dienestrol can be decreased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
Ym150The serum concentration of Dienestrol can be decreased when it is combined with Ym150.Investigational
Food InteractionsNot Available
References
Synthesis Reference

Short, W.F. and Hobday, G.1; U.S. Patent 2,464,203; March 15,1949; assigned to Boots
Pure Drug Company Limited, England.
Adler, E.; U.S. Patent 2,465,505; March 29,1949; assigned to Hoffmann-La Roche Inc.

General ReferencesNot Available
External Links
ATC CodesG03CB01G03CC02
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (75.7 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9971
Blood Brain Barrier-0.7087
Caco-2 permeable+0.8916
P-glycoprotein substrateNon-substrate0.5491
P-glycoprotein inhibitor INon-inhibitor0.7795
P-glycoprotein inhibitor IINon-inhibitor0.9557
Renal organic cation transporterNon-inhibitor0.8322
CYP450 2C9 substrateNon-substrate0.7849
CYP450 2D6 substrateNon-substrate0.8857
CYP450 3A4 substrateNon-substrate0.544
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8605
CYP450 2D6 inhibitorNon-inhibitor0.8201
CYP450 2C19 inhibitorInhibitor0.8993
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8844
Ames testNon AMES toxic0.9658
CarcinogenicityNon-carcinogens0.7133
BiodegradationNot ready biodegradable0.7876
Rat acute toxicity1.8229 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7994
hERG inhibition (predictor II)Non-inhibitor0.8584
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Ortho mcneil pharmaceutical inc
  • Sanofi aventis us llc
  • Solvay pharmaceuticals
Packagers
Dosage forms
FormRouteStrength
CreamVaginal.01 %
Prices
Unit descriptionCostUnit
Dienestrol powder442.23USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point233-234Short, W.F. and Hobday, G.1; U.S. Patent 2,464,203; March 15,1949; assigned to Boots Pure Drug Company Limited, England.
water solubility3 mg/L (at 37 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP5.9Not Available
logS-4.95ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0123 mg/mLALOGPS
logP5.18ALOGPS
logP4.83ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.1ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity84.36 m3·mol-1ChemAxon
Polarizability30.3 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.48 KB)
SpectraNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Phenylpropene
  • Styrene
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Targets

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 tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription fact...
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. Juriansz RL, Huseby RA, Wilcox RB: Interactions of putative estrogens with the intracellular receptor complex in mouse Leydig cells: relationship to preneoplastic hyperplasia. Cancer Res. 1988 Jan 1;48(1):14-8. [PubMed:3334987 ]
  2. Grove RI, Korach KS: Estrogen stimulation of phosphatidylinositol metabolism in mouse uterine tissue. Endocrinology. 1987 Sep;121(3):1083-8. [PubMed:3622377 ]
  3. Kuiper GG, Carlsson B, Grandien K, Enmark E, Haggblad J, Nilsson S, Gustafsson JA: Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology. 1997 Mar;138(3):863-70. [PubMed:9048584 ]
  4. Chae K, Lindzey J, McLachlan JA, Korach KS: Estrogen-dependent gene regulation by an oxidative metabolite of diethylstilbestrol, diethylstilbestrol-4',4"-quinone. Steroids. 1998 Mar;63(3):149-57. [PubMed:9558716 ]
  5. Bovee TF, Helsdingen RJ, Rietjens IM, Keijer J, Hoogenboom RL: Rapid yeast estrogen bioassays stably expressing human estrogen receptors alpha and beta, and green fluorescent protein: a comparison of different compounds with both receptor types. J Steroid Biochem Mol Biol. 2004 Jul;91(3):99-109. [PubMed:15276617 ]
  6. Maru BS, Tobias JH, Rivers C, Caunt CJ, Norman MR, McArdle CA: Potential use of an estrogen-glucocorticoid receptor chimera as a drug screen for tissue selective estrogenic activity. Bone. 2009 Jan;44(1):102-12. doi: 10.1016/j.bone.2008.09.016. Epub 2008 Oct 11. [PubMed:18976723 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23