Identification

Name
Ethinyl Estradiol
Accession Number
DB00977  (APRD00691)
Type
Small Molecule
Groups
Approved
Description

A semisynthetic alkylated estradiol with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally and is often used as the estrogenic component in oral contraceptives. Ethinyl estradiol is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Tri-Cyclen, Triphasil, and Yasmin. The FDA label includes a black box warning that states that combination oral contraceptives should not be used in women over 35 years old who smoke due to the increased risk of serious cardiovascular side effects.

Structure
Thumb
Synonyms
  • 17-ethinyl-3,17-estradiol
  • 17-ethinyl-3,17-oestradiol
  • 17-ethinylestradiol
  • 17alpha-Ethinyl estradiol
  • 17α-ethynylestradiol
  • Ethinylestradiol
  • Ethinylestradiolum
  • Ethinyloestradiol
  • Ethynyl estradiol
  • Etinilestradiol
External IDs
NSC-10973
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Estinyl Tab 0.05mgTablet.05 mgOralSchering Plough1951-12-312000-07-11Canada
Estinyl Tab 0.5mgTablet.5 mgOralSchering Plough1951-12-312000-07-11Canada
Estinyl Tablets 0.02 Mg.Tablet.02 mgOralSchering Plough1951-12-311998-11-17Canada
JolessaKitTeva2003-10-13Not applicableUs0555 912320170913 5456 rktojs
International/Other Brands
Estinyl (Schering)
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AfirmelleEthinyl Estradiol + LevonorgestrelKitAurobindo Pharma2016-11-14Not applicableUs
Alesse 21Ethinyl Estradiol (20 mcg) + Levonorgestrel (100 mcg)TabletOralPfizer1998-01-07Not applicableCanada
Alesse 28Ethinyl Estradiol (20 mcg) + Levonorgestrel (100 mcg)TabletOralPfizer1998-01-07Not applicableCanada
AltaveraEthinyl Estradiol + LevonorgestrelKitSandoz2010-08-03Not applicableUs
Alyacen 1/35Ethinyl Estradiol + NorethisteroneKitGlenmark Pharmaceuticals Inc.,Usa2012-01-19Not applicableUs
Alyacen 1/35Ethinyl Estradiol + NorethisteroneKitA S Medication Solutions2012-01-192017-06-20Us
Alyacen 7/7/7Ethinyl Estradiol + NorethisteroneKitA S Medication Solutions2012-01-192017-06-20Us
Alyacen 7/7/7Ethinyl Estradiol + NorethisteroneKitGlenmark Pharmaceuticals Inc.,Usa2012-01-19Not applicableUs
Alysena 21Ethinyl Estradiol (20 mcg) + Levonorgestrel (100 mcg)TabletOralApotex Corporation2012-11-19Not applicableCanada
Alysena 28Ethinyl Estradiol (20 mcg) + Levonorgestrel (100 mcg)TabletOralApotex Corporation2012-11-19Not applicableCanada
Categories
UNII
423D2T571U
CAS number
57-63-6
Weight
Average: 296.4034
Monoisotopic: 296.177630012
Chemical Formula
C20H24O2
InChI Key
BFPYWIDHMRZLRN-SLHNCBLASA-N
InChI
InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1
IUPAC Name
(1S,10R,11S,14R,15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,14-diol
SMILES
[H][[email protected]@]12CC[[email protected]@](O)(C#C)[[email protected]@]1(C)CC[[email protected]]1([H])C3=C(CC[[email protected]@]21[H])C=C(O)C=C3

Pharmacology

Indication

For treatment of moderate to severe vasomotor symptoms associated with the menopause, female hypogonadism, prostatic carcinoma-palliative therapy of advanced disease, breast cancer, as an oral contraceptive, and as emergency contraceptive.

Structured Indications
Pharmacodynamics

Ethinyl estradiol is a synthetic derivative of the natural estrogen estradiol. It is one of two estrogens currently used in oral contraceptive pills. The other, mestranol, is converted to ethinyl estradiol before it is biologically active. Ethinyl estradiol and norethindrone are used together as an oral contraceptive agent.

Mechanism of action

Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. This cascade is initiated by initially binding to the estrogen receptors. 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
UNuclear receptor subfamily 1 group I member 2
agonist
Human
USex hormone-binding globulinNot AvailableHuman
Absorption

Rapid and complete absorption follows oral intake of ethinyl estradiol (bioavailability 43%).

Volume of distribution
Not Available
Protein binding

97%

Metabolism

Hepatic. Quantitatively, the major metabolic pathway for ethinyl estradiol, both in rats and in humans, is aromatic hydroxylation, as it is for the natural estrogens.

Route of elimination
Not Available
Half life

36 +/- 13 hours

Clearance
Not Available
Toxicity

Oral, mouse LD50: 1737 mg/kg. Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females. The FDA label includes a black box warning that states that combination oral contraceptives with ethinyl estradiol should not be used in women over 35 years old who smoke due to the increased risk of serious cardiovascular side effects.

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 Ethinyl Estradiol 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 Ethinyl Estradiol.Investigational
19-norandrostenedioneThe serum concentration of 19-norandrostenedione can be increased when it is combined with Ethinyl Estradiol.Experimental, Illicit
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be decreased when used in combination with Ethinyl Estradiol.Investigational
3,4-DichloroisocoumarinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with 3,4-Dichloroisocoumarin.Experimental
4-(2-Aminoethyl)Benzenesulfonyl FluorideThe serum concentration of Ethinyl Estradiol 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 Ethinyl Estradiol.Experimental, Illicit
AbciximabEthinyl Estradiol may decrease the anticoagulant activities of Abciximab.Approved
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
AcenocoumarolEthinyl Estradiol may decrease the anticoagulant activities of Acenocoumarol.Approved
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Ethinyl Estradiol.Investigational, Withdrawn
AcitretinThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Acitretin.Approved
AdapaleneThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Adapalene.Approved
AICA ribonucleotideThe therapeutic efficacy of AICA ribonucleotide can be decreased when used in combination with Ethinyl Estradiol.Experimental, Investigational
AlclometasoneThe serum concentration of Alclometasone can be increased when it is combined with Ethinyl Estradiol.Approved
AldosteroneThe serum concentration of Aldosterone can be increased when it is combined with Ethinyl Estradiol.Experimental, Investigational
AlitretinoinThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Alitretinoin.Approved, Investigational
AllicinThe therapeutic efficacy of Allicin can be decreased when used in combination with Ethinyl Estradiol.Investigational
AlogliptinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Alogliptin.Approved
Alpha-1-proteinase inhibitorThe serum concentration of Ethinyl Estradiol 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 Ethinyl Estradiol.Experimental, Investigational
AmcinonideThe serum concentration of Amcinonide can be increased when it is combined with Ethinyl Estradiol.Approved
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Ethinyl Estradiol.Approved
AmiodaroneThe metabolism of Ethinyl Estradiol can be decreased when combined with Amiodarone.Approved, Investigational
AmobarbitalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Amobarbital.Approved, Illicit
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Ethinyl Estradiol.Approved, Investigational
AmprenavirThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Amprenavir.Approved
AnastrozoleThe therapeutic efficacy of Anastrozole can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
AncrodEthinyl Estradiol may decrease the anticoagulant activities of Ancrod.Investigational
AndrostenedioneThe serum concentration of Androstenedione can be increased when it is combined with Ethinyl Estradiol.Experimental, Illicit
AnecortaveThe serum concentration of Anecortave can be increased when it is combined with Ethinyl Estradiol.Investigational
anecortave acetateThe serum concentration of anecortave acetate can be increased when it is combined with Ethinyl Estradiol.Investigational
Anthrax immune globulin humanEthinyl Estradiol may increase the thrombogenic activities of Anthrax immune globulin human.Approved
Antithrombin III humanThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Antithrombin III human.Approved
ApixabanThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Apixaban.Approved
AprepitantThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Aprepitant.Approved, Investigational
AprotininThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Aprotinin.Approved, Withdrawn
ArdeparinEthinyl Estradiol may decrease the anticoagulant activities of Ardeparin.Approved, Investigational, Withdrawn
ArgatrobanThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Argatroban.Approved, Investigational
ArmodafinilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Armodafinil.Approved, Investigational
ArtemetherThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Artemether.Approved
AsunaprevirThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Asunaprevir.Approved, Investigational
AtamestaneThe serum concentration of Atamestane can be increased when it is combined with Ethinyl Estradiol.Investigational
AtazanavirThe metabolism of Ethinyl Estradiol can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Ethinyl Estradiol can be decreased when combined with Atomoxetine.Approved
BalaglitazoneThe therapeutic efficacy of Balaglitazone can be decreased when used in combination with Ethinyl Estradiol.Investigational
BarbexacloneThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Barbexaclone.Experimental
BarbitalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Barbital.Illicit
BatimastatThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Batimastat.Experimental
BecaplerminEthinyl Estradiol may decrease the anticoagulant activities of Becaplermin.Approved, Investigational
Beclomethasone dipropionateThe serum concentration of Beclomethasone dipropionate can be increased when it is combined with Ethinyl Estradiol.Approved, Investigational
Bempedoic acidThe therapeutic efficacy of Bempedoic acid can be decreased when used in combination with Ethinyl Estradiol.Investigational
BenazeprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Benazepril.Approved, Investigational
BenzamidineThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Benzamidine.Experimental
BetamethasoneThe serum concentration of Betamethasone can be increased when it is combined with Ethinyl Estradiol.Approved, Vet Approved
BexaroteneThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Bexarotene.Approved, Investigational
BivalirudinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Bivalirudin.Approved, Investigational
BoceprevirThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Ethinyl Estradiol can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Bosentan.Approved, Investigational
BudesonideThe serum concentration of Budesonide can be increased when it is combined with Ethinyl Estradiol.Approved
BuforminThe therapeutic efficacy of Buformin can be decreased when used in combination with Ethinyl Estradiol.Investigational, Withdrawn
CamostatThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Camostat.Experimental
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Ethinyl Estradiol.Approved
CandoxatrilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Candoxatril.Experimental
CandoxatrilatThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Candoxatrilat.Experimental
Capromab pendetideEthinyl Estradiol may decrease effectiveness of Capromab pendetide as a diagnostic agent.Approved
CaptoprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Captopril.Approved
CarbamazepineThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Carbamazepine.Approved, Investigational
CarbutamideThe therapeutic efficacy of Carbutamide can be decreased when used in combination with Ethinyl Estradiol.Experimental
CastanospermineThe therapeutic efficacy of Castanospermine can be decreased when used in combination with Ethinyl Estradiol.Experimental
CelecoxibCelecoxib may increase the thrombogenic activities of Ethinyl Estradiol.Approved, Investigational
CeritinibThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Ceritinib.Approved
CertoparinEthinyl Estradiol may decrease the anticoagulant activities of Certoparin.Approved, Investigational
Chenodeoxycholic acidThe therapeutic efficacy of Chenodeoxycholic acid can be decreased when used in combination with Ethinyl Estradiol.Approved
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Ethinyl Estradiol.Approved
CholesterolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Cholesterol.Experimental, Investigational
CholestyramineThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Cholestyramine.Approved
Cholic AcidEthinyl Estradiol may decrease the excretion rate of Cholic Acid which could result in a higher serum level.Approved
ChymostatinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Chymostatin.Experimental
CiclesonideThe serum concentration of Ciclesonide can be increased when it is combined with Ethinyl Estradiol.Approved, Investigational
CiglitazoneThe therapeutic efficacy of Ciglitazone can be decreased when used in combination with Ethinyl Estradiol.Experimental
CilastatinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Cilastatin.Approved
CilazaprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Cilazapril.Approved
Citric AcidEthinyl Estradiol may decrease the anticoagulant activities of Citric Acid.Approved, Nutraceutical, Vet Approved
ClarithromycinThe metabolism of Ethinyl Estradiol can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Ethinyl Estradiol can be decreased when combined with Clemastine.Approved
ClobazamThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Clobazam.Approved, Illicit
ClobetasolThe serum concentration of Clobetasol can be increased when it is combined with Ethinyl Estradiol.Investigational
Clobetasol propionateThe serum concentration of Clobetasol propionate can be increased when it is combined with Ethinyl Estradiol.Approved
ClobetasoneThe serum concentration of Clobetasone can be increased when it is combined with Ethinyl Estradiol.Approved
ClocortoloneThe serum concentration of Clocortolone can be increased when it is combined with Ethinyl Estradiol.Approved
ClorindioneEthinyl Estradiol may decrease the anticoagulant activities of Clorindione.Experimental
ClotrimazoleThe metabolism of Ethinyl Estradiol can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Cobicistat.Approved
ColesevelamThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Colesevelam.Approved
ColestipolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Colestipol.Approved
Conestat alfaEthinyl Estradiol may increase the thrombogenic activities of Conestat alfa.Approved
ConivaptanThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Conivaptan.Approved, Investigational
Cortexolone 17α-propionateThe serum concentration of Cortexolone 17α-propionate can be increased when it is combined with Ethinyl Estradiol.Investigational
CorticosteroneThe serum concentration of Corticosterone can be increased when it is combined with Ethinyl Estradiol.Experimental
Cortisone acetateThe serum concentration of Cortisone acetate can be increased when it is combined with Ethinyl Estradiol.Approved
CrizotinibThe metabolism of Ethinyl Estradiol can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Ethinyl Estradiol can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Dabigatran etexilateThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Dabigatran etexilate.Approved
DabrafenibThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Dabrafenib.Approved
DalteparinEthinyl Estradiol may decrease the anticoagulant activities of Dalteparin.Approved
DanaparoidEthinyl Estradiol may decrease the anticoagulant activities of Danaparoid.Approved, Withdrawn
DarexabanThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Darexaban.Investigational
DarunavirThe metabolism of Ethinyl Estradiol can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Deferasirox.Approved, Investigational
DeflazacortThe serum concentration of Deflazacort can be increased when it is combined with Ethinyl Estradiol.Approved
DelanzomibThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Delanzomib.Investigational
DelaprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Delapril.Experimental
DelavirdineThe metabolism of Ethinyl Estradiol can be decreased when combined with Delavirdine.Approved
DeoxyspergualinThe therapeutic efficacy of Deoxyspergualin can be decreased when used in combination with Ethinyl Estradiol.Investigational
DesirudinEthinyl Estradiol may decrease the anticoagulant activities of Desirudin.Approved
DesonideThe serum concentration of Desonide can be increased when it is combined with Ethinyl Estradiol.Approved, Investigational
DesoximetasoneThe serum concentration of Desoximetasone can be increased when it is combined with Ethinyl Estradiol.Approved
Desoxycorticosterone acetateThe serum concentration of Desoxycorticosterone acetate can be increased when it is combined with Ethinyl Estradiol.Approved
Desoxycorticosterone PivalateThe serum concentration of Desoxycorticosterone Pivalate can be increased when it is combined with Ethinyl Estradiol.Experimental, Vet Approved
DexamethasoneThe serum concentration of Dexamethasone can be increased when it is combined with Ethinyl Estradiol.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateThe serum concentration of Dexamethasone isonicotinate can be increased when it is combined with Ethinyl Estradiol.Vet Approved
DextranEthinyl Estradiol may decrease the anticoagulant activities of Dextran.Approved, Vet Approved
Dextran 40Ethinyl Estradiol may decrease the anticoagulant activities of Dextran 40.Approved
Dextran 70Ethinyl Estradiol may decrease the anticoagulant activities of Dextran 70.Approved
Dextran 75Ethinyl Estradiol may decrease the anticoagulant activities of Dextran 75.Approved
DicoumarolEthinyl Estradiol may decrease the anticoagulant activities of Dicoumarol.Approved
DiflorasoneThe serum concentration of Diflorasone can be increased when it is combined with Ethinyl Estradiol.Approved
DifluocortoloneThe serum concentration of Difluocortolone can be increased when it is combined with Ethinyl Estradiol.Approved, Investigational
DifluprednateThe serum concentration of Difluprednate can be increased when it is combined with Ethinyl Estradiol.Approved
DihydroergotamineThe metabolism of Ethinyl Estradiol can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Ethinyl Estradiol can be decreased when combined with Diltiazem.Approved
DiphenadioneEthinyl Estradiol may decrease the anticoagulant activities of Diphenadione.Experimental
DoxycyclineThe metabolism of Ethinyl Estradiol can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Ethinyl Estradiol can be decreased when combined with Dronedarone.Approved
DulaglutideThe therapeutic efficacy of Dulaglutide can be decreased when used in combination with Ethinyl Estradiol.Approved
DyphyllineThe serum concentration of Dyphylline can be increased when it is combined with Ethinyl Estradiol.Approved
EcabetThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Ecabet.Approved, Investigational
Edetic AcidEthinyl Estradiol may decrease the anticoagulant activities of Edetic Acid.Approved, Vet Approved
EdoxabanThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Edoxaban.Approved
ElafinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Elafin.Investigational
ElvitegravirThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Elvitegravir.Approved
EmpagliflozinThe therapeutic efficacy of Empagliflozin can be decreased when used in combination with Ethinyl Estradiol.Approved
EnalaprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Enalaprilat.Approved
EnalkirenThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Enalkiren.Experimental
EnoxaparinEthinyl Estradiol may decrease the anticoagulant activities of Enoxaparin.Approved
EnzalutamideThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Enzalutamide.Approved
Epigallocatechin GallateThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Epigallocatechin Gallate.Investigational
EquileninThe serum concentration of Equilenin can be increased when it is combined with Ethinyl Estradiol.Experimental
EquilinThe serum concentration of Equilin can be increased when it is combined with Ethinyl Estradiol.Approved
ErythromycinThe metabolism of Ethinyl Estradiol can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstroneThe serum concentration of Estrone can be increased when it is combined with Ethinyl Estradiol.Approved
Estrone sulfateThe serum concentration of Estrone sulfate can be increased when it is combined with Ethinyl Estradiol.Approved
Ethyl biscoumacetateEthinyl Estradiol may decrease the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
EtodolacEtodolac may increase the thrombogenic activities of Ethinyl Estradiol.Approved, Investigational, Vet Approved
EtoricoxibEtoricoxib may increase the thrombogenic activities of Ethinyl Estradiol.Approved, Investigational
ExemestaneThe therapeutic efficacy of Exemestane can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
ExenatideThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Exenatide.Approved, Investigational
FaldaprevirThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Faldaprevir.Investigational
FelbamateThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Felbamate.Approved
Ferulic acidEthinyl Estradiol may decrease the anticoagulant activities of Ferulic acid.Experimental
FlibanserinThe serum concentration of Flibanserin can be increased when it is combined with Ethinyl Estradiol.Approved
fluasteroneThe serum concentration of fluasterone can be increased when it is combined with Ethinyl Estradiol.Investigational
FluconazoleThe metabolism of Ethinyl Estradiol can be decreased when combined with Fluconazole.Approved
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Ethinyl Estradiol.Approved
FluindioneEthinyl Estradiol may decrease the anticoagulant activities of Fluindione.Investigational
FlumethasoneThe serum concentration of Flumethasone can be increased when it is combined with Ethinyl Estradiol.Approved, Vet Approved
FlunisolideThe serum concentration of Flunisolide can be increased when it is combined with Ethinyl Estradiol.Approved, Investigational
Fluocinolone AcetonideThe serum concentration of Fluocinolone Acetonide can be increased when it is combined with Ethinyl Estradiol.Approved, Investigational, Vet Approved
FluocinonideThe serum concentration of Fluocinonide can be increased when it is combined with Ethinyl Estradiol.Approved, Investigational
FluocortoloneThe serum concentration of Fluocortolone can be increased when it is combined with Ethinyl Estradiol.Approved, Withdrawn
FluorometholoneThe serum concentration of Fluorometholone can be increased when it is combined with Ethinyl Estradiol.Approved
FluprednideneThe serum concentration of Fluprednidene can be increased when it is combined with Ethinyl Estradiol.Approved, Withdrawn
FluprednisoloneThe serum concentration of Fluprednisolone can be increased when it is combined with Ethinyl Estradiol.Approved
FlurandrenolideThe serum concentration of Flurandrenolide can be increased when it is combined with Ethinyl Estradiol.Approved
Fluticasone furoateThe serum concentration of Fluticasone furoate can be increased when it is combined with Ethinyl Estradiol.Approved
Fluticasone propionateThe serum concentration of Fluticasone propionate can be increased when it is combined with Ethinyl Estradiol.Approved
FluvoxamineThe metabolism of Ethinyl Estradiol can be decreased when combined with Fluvoxamine.Approved, Investigational
FondaparinuxEthinyl Estradiol may decrease the anticoagulant activities of Fondaparinux.Investigational
Fondaparinux sodiumEthinyl Estradiol may decrease the anticoagulant activities of Fondaparinux sodium.Approved, Investigational
FormestaneThe serum concentration of Formestane can be increased when it is combined with Ethinyl Estradiol.Approved, Investigational, Withdrawn
FosamprenavirThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Fosaprepitant.Approved
FosinoprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Fosinopril.Approved
FosphenytoinThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Fusidic Acid.Approved
GabexateThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Gabexate.Investigational
GeldanamycinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Geldanamycin.Experimental, Investigational
GlibornurideThe therapeutic efficacy of Glibornuride can be decreased when used in combination with Ethinyl Estradiol.Investigational, Withdrawn
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Ethinyl Estradiol.Approved
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Ethinyl Estradiol.Approved
GlipizideThe therapeutic efficacy of Glipizide can be decreased when used in combination with Ethinyl Estradiol.Approved
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Ethinyl Estradiol.Approved
GM6001The serum concentration of Ethinyl Estradiol can be decreased when it is combined with GM6001.Experimental
GriseofulvinThe metabolism of Ethinyl Estradiol can be increased when combined with Griseofulvin.Approved, Vet Approved
GusperimusThe therapeutic efficacy of Gusperimus can be decreased when used in combination with Ethinyl Estradiol.Investigational
HalcinonideThe serum concentration of Halcinonide can be increased when it is combined with Ethinyl Estradiol.Approved, Investigational, Withdrawn
HE3286The serum concentration of HE3286 can be increased when it is combined with Ethinyl Estradiol.Investigational
HeparinEthinyl Estradiol may decrease the anticoagulant activities of Heparin.Approved, Investigational
HexobarbitalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Hexobarbital.Approved
Human C1-esterase inhibitorEthinyl Estradiol may increase the thrombogenic activities of Human C1-esterase inhibitor.Approved
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
HydrocortisoneThe serum concentration of Hydrocortisone can be increased when it is combined with Ethinyl Estradiol.Approved, Vet Approved
IdraparinuxThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Idraparinux.Investigational
ImatinibThe metabolism of Ethinyl Estradiol can be decreased when combined with Imatinib.Approved
ImidaprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Imidapril.Investigational
IndinavirThe metabolism of Ethinyl Estradiol can be decreased when combined with Indinavir.Approved
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Ethinyl Estradiol.Approved
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Ethinyl Estradiol.Approved
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Ethinyl Estradiol.Approved
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Ethinyl Estradiol.Approved
Insulin HumanThe therapeutic efficacy of Insulin Human can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Ethinyl Estradiol.Approved
Insulin PorkThe therapeutic efficacy of Insulin Pork can be decreased when used in combination with Ethinyl Estradiol.Approved
IsavuconazoniumThe metabolism of Ethinyl Estradiol can be decreased when combined with Isavuconazonium.Approved, Investigational
IsoflurophateThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Isoflurophate.Approved, Investigational, Withdrawn
IsotretinoinThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Isotretinoin.Approved
IsradipineThe metabolism of Ethinyl Estradiol can be decreased when combined with Isradipine.Approved
IstaroximeThe serum concentration of Istaroxime can be increased when it is combined with Ethinyl Estradiol.Investigational
ItraconazoleThe metabolism of Ethinyl Estradiol can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Ivacaftor.Approved
IxazomibThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Ixazomib.Approved
KetoconazoleThe metabolism of Ethinyl Estradiol can be decreased when combined with Ketoconazole.Approved, Investigational
LamotrigineThe serum concentration of Lamotrigine can be decreased when it is combined with Ethinyl Estradiol.Approved, Investigational
LenalidomideEthinyl Estradiol may increase the thrombogenic activities of Lenalidomide.Approved
LepirudinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Lepirudin.Approved
LetaxabanThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Letaxaban.Investigational
LevothyroxineThe therapeutic efficacy of Levothyroxine can be decreased when used in combination with Ethinyl Estradiol.Approved
LinagliptinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Linagliptin.Approved
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Ethinyl Estradiol.Approved, Vet Approved
LiotrixThe therapeutic efficacy of Liotrix can be decreased when used in combination with Ethinyl Estradiol.Approved
LiraglutideThe therapeutic efficacy of Liraglutide can be decreased when used in combination with Ethinyl Estradiol.Approved
LisinoprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Lisinopril.Approved, Investigational
LopinavirThe metabolism of Ethinyl Estradiol can be decreased when combined with Lopinavir.Approved
LoteprednolThe serum concentration of Loteprednol can be increased when it is combined with Ethinyl Estradiol.Approved
LovastatinThe metabolism of Ethinyl Estradiol can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Lumacaftor.Approved
LumiracoxibLumiracoxib may increase the thrombogenic activities of Ethinyl Estradiol.Approved, Investigational
ME-609The serum concentration of ME-609 can be increased when it is combined with Ethinyl Estradiol.Investigational
MedrysoneThe serum concentration of Medrysone can be increased when it is combined with Ethinyl Estradiol.Approved
MelagatranThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Melagatran.Experimental
MelengestrolThe serum concentration of Melengestrol can be increased when it is combined with Ethinyl Estradiol.Vet Approved
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Ethinyl Estradiol.Approved
MethohexitalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Methohexital.Approved
MethylphenobarbitalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Methylphenobarbital.Approved
MethylprednisoloneThe serum concentration of Methylprednisolone can be increased when it is combined with Ethinyl Estradiol.Approved, Vet Approved
MetreleptinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Metreleptin.Approved
MifepristoneThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Mifepristone.Approved, Investigational
MiglitolThe therapeutic efficacy of Miglitol can be decreased when used in combination with Ethinyl Estradiol.Approved
MiglustatThe therapeutic efficacy of Miglustat can be decreased when used in combination with Ethinyl Estradiol.Approved
MitiglinideThe therapeutic efficacy of Mitiglinide can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
MitotaneThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Mitotane.Approved
ModafinilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Modafinil.Approved, Investigational
MoexiprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Moexipril.Approved
MometasoneThe serum concentration of Mometasone can be increased when it is combined with Ethinyl Estradiol.Approved, Vet Approved
Mycophenolic acidThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Mycophenolic acid.Approved
N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-ProlineThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with N-(3-Propylcarbamoyloxirane-2-Carbonyl)-Isoleucyl-Proline.Experimental
NabumetoneNabumetone may increase the thrombogenic activities of Ethinyl Estradiol.Approved
NadroparinEthinyl Estradiol may decrease the anticoagulant activities of Nadroparin.Approved
NafamostatThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Nafamostat.Approved, Investigational
NafcillinThe metabolism of Ethinyl Estradiol can be increased when combined with Nafcillin.Approved
NateglinideThe therapeutic efficacy of Nateglinide can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
NCX 1022The serum concentration of NCX 1022 can be increased when it is combined with Ethinyl Estradiol.Investigational
NefazodoneThe metabolism of Ethinyl Estradiol can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Ethinyl Estradiol can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Netupitant.Approved
NevirapineThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Nevirapine.Approved
NilotinibThe metabolism of Ethinyl Estradiol can be decreased when combined with Nilotinib.Approved, Investigational
NitroaspirinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Nitroaspirin.Investigational
OlaparibThe metabolism of Ethinyl Estradiol can be decreased when combined with Olaparib.Approved
Oleoyl-estroneThe serum concentration of Oleoyl-estrone can be increased when it is combined with Ethinyl Estradiol.Investigational
OmapatrilatThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Omapatrilat.Investigational
OsimertinibThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Osimertinib.Approved
OspemifeneThe risk or severity of adverse effects can be increased when Ethinyl Estradiol is combined with Ospemifene.Approved
OtamixabanThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Otamixaban.Investigational
OxcarbazepineThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Oxcarbazepine.Approved
PalbociclibThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Palbociclib.Approved
ParamethasoneThe serum concentration of Paramethasone can be increased when it is combined with Ethinyl Estradiol.Approved
ParecoxibParecoxib may increase the thrombogenic activities of Ethinyl Estradiol.Approved
Pentaerythritol TetranitrateEthinyl Estradiol may decrease the anticoagulant activities of Pentaerythritol Tetranitrate.Approved
PentobarbitalThe metabolism of Ethinyl Estradiol can be increased when combined with Pentobarbital.Approved, Vet Approved
Pentosan PolysulfateEthinyl Estradiol may decrease the anticoagulant activities of Pentosan Polysulfate.Approved
PerindoprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Perindopril.Approved
PhenforminThe therapeutic efficacy of Phenformin can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational, Withdrawn
PhenindioneEthinyl Estradiol may decrease the anticoagulant activities of Phenindione.Approved, Investigational
PhenobarbitalThe metabolism of Ethinyl Estradiol can be increased when combined with Phenobarbital.Approved
PhenprocoumonEthinyl Estradiol may decrease the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhenytoinThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Phenytoin.Approved, Vet Approved
PhosphoramidonThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Phosphoramidon.Experimental
PioglitazoneThe therapeutic efficacy of Pioglitazone can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
PosaconazoleThe metabolism of Ethinyl Estradiol can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PramlintideThe therapeutic efficacy of Pramlintide can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
PrasteroneThe risk or severity of adverse effects can be increased when Prasterone is combined with Ethinyl Estradiol.Approved, Nutraceutical
Prasterone sulfateThe serum concentration of Prasterone sulfate can be increased when it is combined with Ethinyl Estradiol.Investigational
PrednicarbateThe serum concentration of Prednicarbate can be increased when it is combined with Ethinyl Estradiol.Approved
PrednisoloneThe serum concentration of Prednisolone can be increased when it is combined with Ethinyl Estradiol.Approved, Vet Approved
PrednisoneThe serum concentration of Prednisone can be increased when it is combined with Ethinyl Estradiol.Approved, Vet Approved
PregnenoloneThe serum concentration of Pregnenolone can be increased when it is combined with Ethinyl Estradiol.Experimental, Investigational
PrimidoneThe metabolism of Ethinyl Estradiol can be increased when combined with Primidone.Approved, Vet Approved
PrinomastatThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Prinomastat.Investigational
Protein CEthinyl Estradiol may decrease the anticoagulant activities of Protein C.Approved
Protein S humanEthinyl Estradiol may decrease the anticoagulant activities of Protein S human.Approved
ProtocatechualdehydeEthinyl Estradiol may decrease the anticoagulant activities of Protocatechualdehyde.Approved
PrucaloprideThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Prucalopride.Approved
QuinaprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Quinapril.Approved, Investigational
RacecadotrilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Racecadotril.Investigational
RamiprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Ramipril.Approved
RanolazineThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Ranolazine.Approved, Investigational
RemikirenThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Remikiren.Approved
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
ReviparinEthinyl Estradiol may decrease the anticoagulant activities of Reviparin.Approved, Investigational
RifabutinThe metabolism of Ethinyl Estradiol can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Ethinyl Estradiol can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Ethinyl Estradiol can be increased when combined with Rifapentine.Approved
RifaximinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Rifaximin.Approved, Investigational
RimexoloneThe serum concentration of Rimexolone can be increased when it is combined with Ethinyl Estradiol.Approved
RivaroxabanThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Rivaroxaban.Approved
RofecoxibRofecoxib may increase the thrombogenic activities of Ethinyl Estradiol.Investigational, Withdrawn
RopiniroleThe serum concentration of Ropinirole can be increased when it is combined with Ethinyl Estradiol.Approved, Investigational
RosiglitazoneThe therapeutic efficacy of Rosiglitazone can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
RufinamideThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Rufinamide.Approved
S-3304The serum concentration of Ethinyl Estradiol can be decreased when it is combined with S-3304.Investigational
SaquinavirThe metabolism of Ethinyl Estradiol can be decreased when combined with Saquinavir.Approved, Investigational
SaxagliptinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Saxagliptin.Approved
SecobarbitalThe therapeutic efficacy of Ethinyl Estradiol 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 Ethinyl Estradiol.Approved, Investigational, Vet Approved
SildenafilThe metabolism of Ethinyl Estradiol can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Simeprevir.Approved
SitagliptinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Sitagliptin.Approved, Investigational
SivelestatThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Sivelestat.Investigational
SomatotropinThe therapeutic efficacy of Somatotropin can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
SotagliflozinThe therapeutic efficacy of Sotagliflozin can be decreased when used in combination with Ethinyl Estradiol.Investigational
SpiraprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Spirapril.Approved
St. John's WortThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Ethinyl Estradiol can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SulodexideEthinyl Estradiol may decrease the anticoagulant activities of Sulodexide.Approved, Investigational
TelaprevirThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Ethinyl Estradiol can be decreased when combined with Telithromycin.Approved
TemocaprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Temocapril.Experimental, Investigational
ThalidomideEthinyl Estradiol may increase the thrombogenic activities of Thalidomide.Approved, Investigational, Withdrawn
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Ethinyl Estradiol.Approved
ThiamylalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Thiamylal.Approved, Vet Approved
ThiopentalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Thiopental.Approved, Vet Approved
ThiorphanThe serum concentration of Ethinyl Estradiol 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 Ethinyl Estradiol.Approved
TiclopidineThe metabolism of Ethinyl Estradiol can be decreased when combined with Ticlopidine.Approved
TioclomarolEthinyl Estradiol may decrease the anticoagulant activities of Tioclomarol.Experimental
TipranavirEthinyl Estradiol may increase the dermatologic adverse activities of Tipranavir.Approved, Investigational
TixocortolThe serum concentration of Tixocortol can be increased when it is combined with Ethinyl Estradiol.Approved
TocilizumabThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Tocilizumab.Approved
TolazamideThe therapeutic efficacy of Tolazamide can be decreased when used in combination with Ethinyl Estradiol.Approved
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Ethinyl Estradiol.Approved
TopiramateThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Topiramate.Approved
TrandolaprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Trandolapril.Approved
Tranexamic AcidEthinyl Estradiol may increase the thrombogenic activities of Tranexamic Acid.Approved
TretinoinThe therapeutic efficacy of Ethinyl Estradiol 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 Ethinyl Estradiol.Approved, Vet Approved
TroglitazoneThe therapeutic efficacy of Troglitazone can be decreased when used in combination with Ethinyl Estradiol.Investigational, Withdrawn
TroxerutinEthinyl Estradiol may decrease the anticoagulant activities of Troxerutin.Investigational
UbenimexThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Ubenimex.Experimental, Investigational
UlinastatinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Ulinastatin.Investigational
UlobetasolThe serum concentration of Ulobetasol can be increased when it is combined with Ethinyl Estradiol.Approved
Ursodeoxycholic acidThe therapeutic efficacy of Ursodeoxycholic acid can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
ValdecoxibValdecoxib may increase the thrombogenic activities of Ethinyl Estradiol.Investigational, Withdrawn
VenlafaxineThe metabolism of Ethinyl Estradiol can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Ethinyl Estradiol can be decreased when combined with Verapamil.Approved
VildagliptinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Vildagliptin.Approved, Investigational
Vitamin CThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Vitamin C.Approved, Nutraceutical
VogliboseThe therapeutic efficacy of Voglibose can be decreased when used in combination with Ethinyl Estradiol.Approved, Investigational
VoriconazoleThe metabolism of Ethinyl Estradiol can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinEthinyl Estradiol may decrease the anticoagulant activities of Warfarin.Approved
XimelagatranThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Ximelagatran.Approved, Investigational, Withdrawn
Z-Val-Ala-Asp fluoromethyl ketoneThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Z-Val-Ala-Asp fluoromethyl ketone.Experimental
ZiprasidoneThe metabolism of Ethinyl Estradiol can be decreased when combined with Ziprasidone.Approved
ZofenoprilThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Zofenopril.Experimental
Food Interactions
Not Available

References

Synthesis Reference

Andreas Sachse, "Method of female hormonal contraception using a fixed extended cycle hormonal preparation containing dienogest and ethinyl estradiol." U.S. Patent US20060079491, issued April 13, 2006.

US20060079491
General References
Not Available
External Links
Human Metabolome Database
HMDB01926
KEGG Drug
D00554
KEGG Compound
C07534
PubChem Compound
5991
PubChem Substance
46508618
ChemSpider
5770
BindingDB
50187243
ChEBI
4903
ChEMBL
CHEMBL691
Therapeutic Targets Database
DAP001018
PharmGKB
PA449527
HET
3WF
RxList
RxList Drug Page
Wikipedia
Ethinylestradiol
ATC Codes
G03AA04 — Megestrol and ethinylestradiolG03AA03 — Lynestrenol and ethinylestradiolG03AA10 — Gestodene and ethinylestradiolG03AA08 — Medroxyprogesterone and ethinylestradiolG03AB07 — Chlormadinone and ethinylestradiolG03AA11 — Norgestimate and ethinylestradiolG03AB01 — Megestrol and ethinylestradiolG03AB05 — Desogestrel and ethinylestradiolG03AA09 — Desogestrel and ethinylestradiolG03AB02 — Lynestrenol and ethinylestradiolG03CA01 — EthinylestradiolG03AB03 — Levonorgestrel and ethinylestradiolL02AA03 — EthinylestradiolG03AA15 — Chlormadinone and ethinylestradiolG03AA06 — Norgestrel and ethinylestradiolG03AB06 — Gestodene and ethinylestradiolG03AA13 — Norelgestromin and ethinylestradiolG03AA02 — Quingestanol and ethinylestradiolG03AB04 — Norethisterone and ethinylestradiolG03AA07 — Levonorgestrel and ethinylestradiolG03AA05 — Norethisterone and ethinylestradiolG03AA01 — Etynodiol and ethinylestradiolG03AA16 — Dienogest and ethinylestradiolG03AA12 — Drospirenone and ethinylestradiol
AHFS Codes
  • 68:16.04 — Estrogens
PDB Entries
4x1f / 4x1g
FDA label
Download (470 KB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingSupportive CareEndometriosis of Uterus1
1Active Not RecruitingTreatmentRheumatoid Arthritis1
1CompletedNot AvailableBioequivalence1
1CompletedNot AvailableChronic Hepatitis C Infection1
1CompletedNot AvailableHealthy Volunteers4
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
1CompletedBasic ScienceFollicle Count / Follicle Size / Induction of follicle development / Oral Contraceptives (OC) / Ovarian Follicle1
1CompletedBasic ScienceHIV-infection/Aids1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceHealthy Volunteers / Pharmacokinetics of Mirabegron1
1CompletedOtherHealthy Female Volunteers / Type 2 Diabetes Mellitus1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentContraception2
1CompletedTreatmentDiabetes Mellitus (DM) / Type 2 Diabetes Mellitus1
1CompletedTreatmentHIV-infection/Aids / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentHealthy Volunteers4
1CompletedTreatmentHepatitis C, Chronic1
1CompletedTreatmentMajor Depressive Disorder (MDD)1
1CompletedTreatmentType 2 Diabetes Mellitus2
1RecruitingHealth Services ResearchHuman Immunodeficiency Virus (HIV)1
1RecruitingOtherHealthy Volunteers1
1RecruitingPreventionContraception1
1RecruitingTreatmentArthritic Psoriasis / Inflammatory Bowel Diseases (IBD) / Psoriasis / Systemic Lupus Erythematosus (SLE)1
1RecruitingTreatmentDrug Interactions1
1RecruitingTreatmentHealthy Volunteers1
1RecruitingTreatmentTumors, Solid1
1TerminatedNot AvailableCystic Fibrosis Exacerbations While on and Off Hormonal Contraception1
1TerminatedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
1TerminatedTreatmentHealthy Volunteers1
1Unknown StatusTreatmentPolycystic Ovaries Syndrome1
1, 2Active Not RecruitingPreventionContraception / Hemostasis Parameter / Liver Metabolism1
2Active Not RecruitingTreatmentPolycystic Ovarian Syndrome1
2CompletedBasic ScienceHemostasis / Oral Contraceptives (OC)2
2CompletedPreventionBreakthrough Bleeding1
2CompletedPreventionContraception2
2CompletedPreventionEndometrial Cancers1
2CompletedPreventionHuman Immunodeficiency Virus (HIV) Infections / Pregnancy1
2CompletedPreventionMigraines1
2CompletedTreatmentBone Mineral Density1
2CompletedTreatmentContraception1
2CompletedTreatmentContraception / Ovulation Inhibition1
2CompletedTreatmentDysmenorrhea1
2CompletedTreatmentOral Contraceptives (OC)1
2CompletedTreatmentOvulation1
2CompletedTreatmentOvulation Suppression1
2RecruitingPreventionPrevention of Pregnancy1
2RecruitingTreatmentAnorexia Nervosa (AN)1
2RecruitingTreatmentPolycystic Ovarian Syndrome1
2TerminatedTreatmentContraception / Ovulation Inhibition1
2TerminatedTreatmentDepression / PMDD / Premenstrual Dysphoric Disorder / Premenstrual Syndrome1
2TerminatedTreatmentHidradenitis Suppurativa (HS)1
2Unknown StatusTreatmentContraception1
2, 3CompletedTreatmentFailed Induction of Labor1
3Active Not RecruitingTreatmentContraception1
3CompletedEducational/Counseling/TrainingOral Contraceptives (OC)1
3CompletedPreventionContraception13
3CompletedPreventionContraception / Neural Tube Defects (NTDs) / Oral Contraceptives (OC)1
3CompletedPreventionContraception / Oral Contraceptives (OC) / Ovulation Inhibition1
3CompletedTreatmentAcne Vulgaris4
3CompletedTreatmentContraception1
3CompletedTreatmentDysmenorrhea1
3CompletedTreatmentHealthy Volunteers4
3CompletedTreatmentOral Contraceptives (OC)1
3CompletedTreatmentPolycystic Ovaries Syndrome2
3CompletedTreatmentPremenstrual Dysphoric Disorder ( PMDD)1
3CompletedTreatmentPremenstrual Syndrome1
3CompletedTreatmentPrimary Dysmenorrhoea1
3CompletedTreatmentSystemic Lupus Erythematosus (SLE)1
3CompletedTreatmentTurner's Syndrome1
3RecruitingTreatmentBladder Cancers / Transitional Cell Carcinoma / Ureteral Cancer1
3RecruitingTreatmentCancer, Breast1
3RecruitingTreatmentExercise-related Amenorrhea1
3RecruitingTreatmentPrimary Ovarian Insufficiency1
3TerminatedPreventionContraception1
3Unknown StatusNot AvailableContraceptive Affecting Blood Pressure / Contraceptive Affecting the Autonomic Nervous System1
3Unknown StatusTreatmentOral Contraceptives (OC)1
3WithdrawnNot AvailableMetrorrhagia1
3WithdrawnTreatmentOsteopenia1
4Active Not RecruitingBasic ScienceCardiovascular Risks / Insulin Sensitivity / Perimenopausal Disorder1
4Active Not RecruitingPreventionBMI >30 kg/m2 / Cardiovascular Disease (CVD) / Insulin Resistance / Metabolic Syndromes1
4Active Not RecruitingTreatmentContraception1
4Active Not RecruitingTreatmentPolycystic Ovaries Syndrome1
4CompletedBasic ScienceAdverse Effect of Oral Contraceptives, Subsequent Encounter1
4CompletedBasic ScienceContraception1
4CompletedDiagnosticBody Weights / Contraceptive Usage1
4CompletedPreventionContraception1
4CompletedTreatmentContraception1
4CompletedTreatmentContraception / Menopause / Quality of Life1
4CompletedTreatmentHealthy Volunteers1
4CompletedTreatmentInfertilities2
4CompletedTreatmentPolycystic Ovaries Syndrome1
4CompletedTreatmentPost coital contraception1
4CompletedTreatmentPremature Ovarian Failure (POF)1
4CompletedTreatmentPremenstrual Dysphoric Disorder1
4CompletedTreatmentPremenstrual Syndrome1
4CompletedTreatmentPrimary Dysmenorrhoea1
4Enrolling by InvitationTreatmentBody Weight Changes1
4Not Yet RecruitingPreventionHealthy, Reproductive Age Women / Post coital contraception1
4RecruitingBasic ScienceBone; Disorder, Development and Growth1
4RecruitingBasic ScienceContraception1
4RecruitingBasic ScienceOther Disorders of Bone Development and Growth1
4RecruitingPreventionBacterial Vaginosis (BV)1
4RecruitingPreventionBacterial Vaginosis (BV) / Human Immunodeficiency Virus (HIV)1
4RecruitingTreatmentContraception / Human Immunodeficiency Virus (HIV)1
4RecruitingTreatmentDysmenorrhea / Endometriosis / Interstitial Cystitis / Migraine Disorders / Pain, Chronic / Pelvic Pain / Visceral Pain1
4TerminatedNot AvailableInfertilities1
4TerminatedTreatmentAbnormal Uterine Bleeding, Unspecified / Uterine Bleeding Heavy1
4Unknown StatusNot AvailableDysmenorrhea / Endometriotic Cysts / Painful Intercourse / Pelvic Pain1
4Unknown StatusPreventionHyperandrogenism / Menstrual Irregularities / Polycystic Ovarian Syndrome1
4Unknown StatusTreatmentBacterial Vaginosis (BV)1
4Unknown StatusTreatmentContraceptive Methods Comparison1
4Unknown StatusTreatmentMenstrual Problem1
4WithdrawnTreatmentInfertilities1
Not AvailableActive Not RecruitingNot AvailableContraception / Human Immunodeficiency Virus (HIV) / Immune Cells (Mucosal and Systemic)1
Not AvailableActive Not RecruitingNot AvailableDysmenorrhea1
Not AvailableActive Not RecruitingTreatmentEndometriosis / Infertilities1
Not AvailableCompletedNot AvailableAcne Vulgaris2
Not AvailableCompletedNot AvailableAcne / Contraception / Premenstrual Syndrome1
Not AvailableCompletedNot AvailableContraception4
Not AvailableCompletedNot AvailableContraceptive Usage / Vaginal Epithelial Disruption1
Not AvailableCompletedNot AvailableHormonal Contraception1
Not AvailableCompletedNot AvailableMetabolic Syndromes / Polycystic Ovaries Syndrome1
Not AvailableCompletedNot AvailablePharmacokinetics1
Not AvailableCompletedBasic ScienceCoronary Heart Disease (CHD)1
Not AvailableCompletedHealth Services ResearchOvarian Follicle1
Not AvailableCompletedTreatmentContraception1
Not AvailableCompletedTreatmentContraception: Optional Applicator for Insertion of Vaginal Ring1
Not AvailableCompletedTreatmentDepression / Premenstrual Syndrome1
Not AvailableCompletedTreatmentHealthy Volunteers1
Not AvailableCompletedTreatmentHypermenorrhea1
Not AvailableCompletedTreatmentInsulin Resistance / Polycystic Ovaries Syndrome1
Not AvailableCompletedTreatmentSystemic Lupus Erythematosus (SLE)1
Not AvailableCompletedTreatmentTemporomandibular Joint Disorders1
Not AvailableCompletedTreatmentThrombosis, Venous1
Not AvailableNot Yet RecruitingTreatmentPremature Menopause / Primary Ovarian Insufficiency1
Not AvailableRecruitingNot AvailableInfertilities1
Not AvailableRecruitingBasic ScienceCystic Fibrosis (CF)1
Not AvailableRecruitingTreatmentHyperandrogenism / Metabolic Cardiovascular Syndrome1
Not AvailableTerminatedBasic ScienceContraception1
Not AvailableTerminatedPreventionAdolescents Seeking Contraception / Contraception Desired1
Not AvailableTerminatedTreatmentIn-Vitro Fertilization / Infertilities1
Not AvailableUnknown StatusBasic ScienceOral Contraceptives (OC)1
Not AvailableUnknown StatusTreatmentEndothelial Dysfunction / Polycystic Ovaries Syndrome1
Not AvailableUnknown StatusTreatmentFemale Contraception1
Not AvailableWithdrawnTreatmentDysmenorrhea / Menstruation Disorders / Menstruation Disturbances1

Pharmacoeconomics

Manufacturers
  • Schering corp sub schering plough corp
  • Pharmacia and upjohn co
  • Organon usa inc
Packagers
Dosage forms
FormRouteStrength
TabletOral.05 mg
TabletOral.5 mg
TabletOral.02 mg
Patch, extended releaseTransdermal
Tablet, film coatedOral
Tablet, chewableOral
TabletOral
Kit
KitOral
Insert, extended releaseVaginal
RingVaginal
PatchTransdermal
Kit
Prices
Unit descriptionCostUnit
Ethinyl estradiol powder140.0USD g
Ortho-Cyclen (28) 28 0.25-35 mg-mcg tablet Disp Pack38.99USD disp
Ortho tri-cyclen lo tablet2.68USD tablet
Ortho-cyclen 28 tablet1.13USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6156742No2000-12-052020-12-05Us
US6787531No2000-08-312020-08-31Us
US6933395No1997-08-112017-08-11Us
US5876746No1995-11-202015-11-20Us
US5989581No1998-04-082018-04-08Us
US6214815Yes1999-12-092019-12-09Us
US6667050No1999-04-062019-04-06Us
US5898032No1997-06-232017-06-23Us
USRE39861No1997-06-232017-06-23Us
US6987101No1997-12-222017-12-22Us
US7163931No2001-12-202021-12-20Us
US6958326No2001-12-202021-12-20Us
US5798338No1995-07-102015-07-10Us
US7320969No2004-01-302024-01-30Us
US7615545No2003-06-152023-06-15Us
US7855190No2008-12-052028-12-05Us
US7858605No2003-06-232023-06-23Us
US6500814No1998-09-032018-09-03Us
US7704984No2009-02-022029-02-02Us
US6441168No2002-07-302022-07-30Us
US8617597No2010-02-082030-02-08Us
US8450299No2005-10-072025-10-07Us
US8415332No2009-03-112029-03-11Us
US6652880No2000-03-292020-03-29Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)142-144Inhoffen, H.H. and Hohlweg, W.; U.S. Patent 2,265,976; December 9, 1941; assigned to Schering Corp.
water solubility11.3 mg/L (at 27 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.67HANSCH,C ET AL. (1995)
logS-4.3ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.00677 mg/mLALOGPS
logP3.63ALOGPS
logP3.9ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity87.37 m3·mol-1ChemAxon
Polarizability34.53 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9965
Blood Brain Barrier+0.8546
Caco-2 permeable+0.8638
P-glycoprotein substrateSubstrate0.6892
P-glycoprotein inhibitor INon-inhibitor0.9006
P-glycoprotein inhibitor IINon-inhibitor0.9449
Renal organic cation transporterNon-inhibitor0.84
CYP450 2C9 substrateNon-substrate0.7178
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.715
CYP450 1A2 substrateInhibitor0.8941
CYP450 2C9 inhibitorNon-inhibitor0.9186
CYP450 2D6 inhibitorNon-inhibitor0.9506
CYP450 2C19 inhibitorNon-inhibitor0.6641
CYP450 3A4 inhibitorInhibitor0.5224
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6776
Ames testNon AMES toxic0.9155
CarcinogenicityNon-carcinogens0.8519
BiodegradationNot ready biodegradable0.9879
Rat acute toxicity2.4584 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8805
hERG inhibition (predictor II)Inhibitor0.5788
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.42 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-03di-0890000000-5219bc8ac1212313c9c0
Mass Spectrum (Electron Ionization)MSsplash10-03dj-2980000000-831c8190c59f98fc8623
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-000b-0290000000-0ef72fb5e00440b9ff50
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-000i-0960000000-945d82a0ab94f246ac88
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-056s-2910000000-0d38daebb87a39304e91
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-03di-0890000000-7a166e952207cf7bc1d3
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
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-hydroxysteroids / 17-hydroxysteroids / Phenanthrenes and derivatives / Tetralins / 1-hydroxy-2-unsubstituted benzenoids / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Acetylides / Hydrocarbon derivatives
Substituents
Estrogen-skeleton / 3-hydroxysteroid / Hydroxysteroid / 17-hydroxysteroid / Phenanthrene / Tetralin / 1-hydroxy-2-unsubstituted benzenoid / Benzenoid / Ynone / Cyclic alcohol
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
terminal acetylenic compound, 17-hydroxy steroid, 3-hydroxy steroid (CHEBI:4903) / C18 steroids (estrogens) and derivatives (C07534) / C18 steroids (estrogens) and derivatives (LMST02010036)

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. Micevych PE, Chaban V, Ogi J, Dewing P, Lu JK, Sinchak K: Estradiol stimulates progesterone synthesis in hypothalamic astrocyte cultures. Endocrinology. 2007 Feb;148(2):782-9. Epub 2006 Nov 9. [PubMed:17095591]
  2. Garcia-Segura LM, Sanz A, Mendez P: Cross-talk between IGF-I and estradiol in the brain: focus on neuroprotection. Neuroendocrinology. 2006;84(4):275-9. Epub 2006 Nov 23. [PubMed:17124377]
  3. Brama M, Gnessi L, Basciani S, Cerulli N, Politi L, Spera G, Mariani S, Cherubini S, Scotto d'Abusco A, Scandurra R, Migliaccio S: Cadmium induces mitogenic signaling in breast cancer cell by an ERalpha-dependent mechanism. Mol Cell Endocrinol. 2007 Jan 29;264(1-2):102-8. Epub 2006 Nov 27. [PubMed:17125913]
  4. Lehnes K, Winder AD, Alfonso C, Kasid N, Simoneaux M, Summe H, Morgan E, Iann MC, Duncan J, Eagan M, Tavaluc R, Evans CH Jr, Russell R, Wang A, Hu F, Stoica A: The effect of estradiol on in vivo tumorigenesis is modulated by the human epidermal growth factor receptor 2/phosphatidylinositol 3-kinase/Akt1 pathway. Endocrinology. 2007 Mar;148(3):1171-80. Epub 2006 Nov 30. [PubMed:17138652]
  5. Mukai H, Tsurugizawa T, Ogiue-Ikeda M, Murakami G, Hojo Y, Ishii H, Kimoto T, Kawato S: Local neurosteroid production in the hippocampus: influence on synaptic plasticity of memory. Neuroendocrinology. 2006;84(4):255-63. Epub 2006 Dec 1. [PubMed:17142999]
  6. Notch EG, Mayer GD: 17alpha-Ethinylestradiol hinders nucleotide excision repair in zebrafish liver cells. Aquat Toxicol. 2009 Dec 13;95(4):273-8. doi: 10.1016/j.aquatox.2009.01.001. Epub 2009 Jan 23. [PubMed:19237207]
  7. Bennink HJ: Reprint of Are all estrogens the same? Maturitas. 2008 Sep-Oct;61(1-2):195-201. [PubMed:19434891]
  8. 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
Unknown
Actions
Agonist
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. Xue Y, Moore LB, Orans J, Peng L, Bencharit S, Kliewer SA, Redinbo MR: Crystal structure of the pregnane X receptor-estradiol complex provides insights into endobiotic recognition. Mol Endocrinol. 2007 May;21(5):1028-38. Epub 2007 Feb 27. [PubMed:17327420]
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

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. Wang B, Sanchez RI, Franklin RB, Evans DC, Huskey SE: The involvement of CYP3A4 and CYP2C9 in the metabolism of 17 alpha-ethinylestradiol. Drug Metab Dispos. 2004 Nov;32(11):1209-12. Epub 2004 Aug 10. [PubMed:15304426]
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. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Lee JM, Trauner M, Soroka CJ, Stieger B, Meier PJ, Boyer JL: Expression of the bile salt export pump is maintained after chronic cholestasis in the rat. Gastroenterology. 2000 Jan;118(1):163-72. [PubMed:10611165]
  2. Huang L, Smit JW, Meijer DK, Vore M: Mrp2 is essential for estradiol-17beta(beta-D-glucuronide)-induced cholestasis in rats. Hepatology. 2000 Jul;32(1):66-72. [PubMed:10869290]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Virus receptor activity
Specific Function
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presenc...
Gene Name
SLC10A1
Uniprot ID
Q14973
Uniprot Name
Sodium/bile acid cotransporter
Molecular Weight
38118.64 Da
References
  1. Lee JM, Trauner M, Soroka CJ, Stieger B, Meier PJ, Boyer JL: Expression of the bile salt export pump is maintained after chronic cholestasis in the rat. Gastroenterology. 2000 Jan;118(1):163-72. [PubMed:10611165]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Kauffmann HM, Schrenk D: Sequence analysis and functional characterization of the 5'-flanking region of the rat multidrug resistance protein 2 (mrp2) gene. Biochem Biophys Res Commun. 1998 Apr 17;245(2):325-31. [PubMed:9571149]
  2. Trauner M, Arrese M, Soroka CJ, Ananthanarayanan M, Koeppel TA, Schlosser SF, Suchy FJ, Keppler D, Boyer JL: The rat canalicular conjugate export pump (Mrp2) is down-regulated in intrahepatic and obstructive cholestasis. Gastroenterology. 1997 Jul;113(1):255-64. [PubMed:9207286]
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. Kim WY, Benet LZ: P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharm Res. 2004 Jul;21(7):1284-93. [PubMed:15290871]

Drug created on June 13, 2005 07:24 / Updated on December 10, 2017 17:18