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Identification
NameEthinyl Estradiol
Accession NumberDB00977  (APRD00691)
TypeSmall Molecule
GroupsApproved
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 [PubChem]. 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 alpha-Ethinylestradiol
17 alpha-Ethynylestradiol
17 alpha-Ethynyloestradiol
17-ethinyl-3,17-estradiol
17-ethinyl-3,17-oestradiol
17-ethinylestradiol
17alpha-Ethinyl estradiol
17α-ethynylestradiol
Ethinyl-Oestranol
Ethinylestradiol
Ethinylestradiolum
Ethinylestriol
Ethinyloestradiol
Ethynyl estradiol
Ethynylestradiol
Ethynyloestradiol
Etinilestradiol
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Estinyl Tab 0.05mgtablet.05 mgoralSchering Plough Canada Inc1951-12-312000-07-11Canada
Estinyl Tab 0.5mgtablet.5 mgoralSchering Plough Canada Inc1951-12-312000-07-11Canada
Estinyl Tablets 0.02 Mg.tablet.02 mgoralSchering Plough Canada Inc1951-12-311998-11-17Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
EstinylSchering
Brand mixtures
NameLabellerIngredients
Alesse 21Pfizer Canada Inc
Alesse 28Pfizer Canada Inc
AltaveraSandoz Inc
Alyacen 1/35Glenmark Pharmaceuticals Inc., Usa
Alyacen 7/7/7Glenmark Pharmaceuticals Inc., Usa
Alysena 21Apotex Inc
Alysena 28Apotex Inc
AmethystWatson Pharma, Inc.
ApriBarr Laboratories Inc.
Apri 21Teva Canada Limited
Apri 28Teva Canada Limited
AranelleBarr Laboratories Inc.
AubraAfaxys Inc.
AvianeBarr Laboratories Inc.
Aviane 21Teva Canada Limited
Aviane 28Teva Canada Limited
Aviane 28 DayRebel Distributors Corp
BalzivaBarr Laboratories Inc.
Blisovi 24 FeLupin Pharmaceuticals, Inc.
Blisovi Fe 1.5/30Lupin Pharmaceuticals, Inc.
Blisovi Fe 1/20Lupin Pharmaceuticals, Inc.
BreviconActavis Pharma, Inc.
Brevicon 0.5/35 21 TabSyntex Inc.
Brevicon 0.5/35 28 TabSyntex Inc.
Brevicon 0.5/35 Tablets (21-day Pack)Pfizer Canada Inc
Brevicon 0.5/35 Tablets (28-day Pack)Pfizer Canada Inc
Brevicon 1/35 21 TabSyntex Inc.
Brevicon 1/35 28 TabSyntex Inc.
Brevicon 1/35 Tablets (21-day Pack)Pfizer Canada Inc
Brevicon 1/35 Tablets (28-day Pack)Pfizer Canada Inc
BriellynGlenmark Pharmaceuticals Inc., Usa
CamreseTeva Pharmaceuticals USA Inc
CamreseloTeva Pharmaceuticals USA Inc
CaziantWatson Pharma, Inc.
Centrisa 21Patriot A Division Of Janssen Inc
Centrisa 28Patriot A Division Of Janssen Inc
Centrisa Lo 21Patriot A Division Of Janssen Inc
Centrisa Lo 28Patriot A Division Of Janssen Inc
ChatealAfaxys Inc.
Cléo -35Aspri Pharma Canada Inc
CryselleBarr Laboratories Inc.
Cyclafem 1/35Qualitest Pharmaceuticals
Cyclafem 7/7/7Qualitest Pharmaceuticals
Cyclen Tablets (21 Day)Janssen Inc
Cyclen Tablets (28 Day)Janssen Inc
CyclessaOrganon USA Inc.
Cyestra-35Paladin Labs Inc
CyredAfaxys Inc.
Dasetta 1/35Northstar Rx LLC
Dasetta 7/7/7Northstar Rx LLC
DayseeLupin Pharmaceuticals, Inc.
DelylaOhm Laboratories Inc.
Demulen 30 (21 Day Pack)Pfizer Canada Inc
Demulen 30 (28 Day Pack)Pfizer Canada Inc
Demulen 50 (21 Day Pack)Pfizer Canada Inc
Demulen 50 (28 Day Pack)Pfizer Canada Inc
DesogenOrganon USA Inc.
Desogestrel and Ethinyl EstradiolNorthstar Rx LLC
Diane-35Bayer Inc
Drospirenone and Ethinyl EstradiolMylan Pharmaceuticals Inc.
Drospirenone and Ethinyl Estradiol Tablets 21Famy Care Ltd
Drospirenone and Ethinyl Estradiol Tablets 28Famy Care Ltd
Drospirenone and Ethinyl Estradiol Tablets USP (21-day Regimen)Glenmark Generics Canada Inc
Drospirenone and Ethinyl Estradiol Tablets USP (28-day Regimen)Glenmark Generics Canada Inc
ElinestNorthstar Rx LLC
EmoquetteQualitest Pharmaceuticals
EnpresseBarr Laboratories Inc.
EnskyceLupin Pharmaceuticals, Inc.
Esme 21Mylan Pharmaceuticals Ulc
Esme 28Mylan Pharmaceuticals Ulc
EstaryllaSandoz Inc
Evra -(6/0.60)Janssen Inc
Evra -(6/0.75)Janssen Inc
FalessaAvion Pharmaceuticals, Llc
FalminaNorthstar Rx LLC
Femcon FeWarner Chilcott (US), LLC
FemhrtWarner Chilcott (US), LLC
Freya 21Mylan Pharmaceuticals Ulc
Freya 28Mylan Pharmaceuticals Ulc
FyavolvLupin Pharmaceuticals, Inc.
GeneressActavis Specialty Pharmaceuticals Co
GianviTeva Pharmaceuticals USA Inc
GildagiaQualitest Pharmaceuticals
Gildess 1.5/30Qualitest Pharmaceuticals
Gildess 1/20Qualitest Pharmaceuticals
IndayoMylan Pharmaceuticals Ulc
IntrovaleSandoz Inc
Jevantique LoActavis Pharma, Inc.
JinteliTeva Pharmaceuticals USA Inc
JolessaPhysicians Total Care, Inc.
JuleberNorthstar Rx LLC
Junel 1.5/30Barr Laboratories Inc.
Junel 1/20Barr Laboratories Inc.
Junel Fe 1.5/30Barr Laboratories Inc.
Junel Fe 1/20Barr Laboratories Inc.
Junel Fe 24Teva Pharmaceuticals USA Inc
Kaitlib FeLupin Pharmaceuticals, Inc.
Kelnor 1/35Barr Laboratories Inc.
KimidessQualitest Pharmaceuticals
KurveloLupin Pharmaceuticals, Inc.
LeenaActavis Pharma, Inc.
LessinaBarr Laboratories Inc.
LevonestNorthstar Rx LLC
Levonorgestrel and Ethinyl EstradiolMylan Pharmaceuticals Inc.
Levonorgestrel and Ethinyl Estradiol and Ethinyl EstradiolLupin Pharmaceuticals, Inc.
Levonorgestrel and Ethinyl Estradiol Tablets, 0.1 Mg/0.02 mgLUPIN LIMITED
LevoraRebel Distributors Corp
Linessa 21Aspen Pharma Trading Limited
Linessa 28Aspen Pharma Trading Limited
Lo Loestrin FeWarner Chilcott (US), LLC
Lo Minastrin FeWarner Chilcott (US), LLC
Lo-femenal 21 TabletsPfizer Canada Inc
Lo/ovral-28A S Medication Solutions Llc
Loestrin 1.5/30Warner Chilcott Canada Co
Loestrin 1.5/30 21 DayTeva Women's Health, Inc.
Loestrin 1/20 21 DayTeva Women's Health, Inc.
Loestrin 21 1.5/30 21 DayTeva Women's Health, Inc.
Loestrin 21 1/20 21 DayTeva Women's Health, Inc.
Loestrin 24 FeWarner Chilcott (US), LLC
LoloWarner Chilcott Canada Co
Lomedia 24 FeAmneal Pharmaceuticals of New York, LLC
LorynaSandoz Inc
Low-ogestrelWatson Pharma, Inc.
LuteraWatson Pharma, Inc.
Lutera 21Cobalt Pharmaceuticals Company
Lutera 28Cobalt Pharmaceuticals Company
Marfem 21Novopharm Limited
Marfem 28Novopharm Limited
MarlissaGlenmark Pharmaceuticals Inc., Usa
Marvelon 21Merck Canada Inc
Marvelon 28Merck Canada Inc
MicrogestinActavis Pharma, Inc.
Min-ovral 21Pfizer Canada Inc
Min-ovral 21 TabWyeth Ltd.
Min-ovral 28Pfizer Canada Inc
Min-ovral 28 TabWyeth Ltd.
Minastrin 24 FeWarner Chilcott (US), LLC
Minestrin 1/20Warner Chilcott Canada Co
Mirvala 21Apotex Inc
Mirvala 28Apotex Inc
ModiconJanssen Pharmaceuticals, Inc.
Mono-linyahNorthstar Rx LLC
MononessaActavis Pharma, Inc
MyaApotex Inc
MyzilraQualitest Pharmaceuticals
NeconRebel Distributors Corp
Necon 1/35Watson Pharma, Inc.
Necon 777Actavis Pharma, Inc.
Necon 777 777Dispensing Solutions, Inc.
NikkiLupin Pharmaceuticals, Inc.
Norethindrone Acetate and Ethinyl EstradiolMylan Pharmaceuticals Inc.
Norethindrone and Ethinyl Estradiol and Ferrous FumarateLupin Pharmaceuticals, Inc.
Norgestimate and Ethinyl EstradiolMylan Pharmaceuticals Inc.
NorinylActavis Pharma, Inc.
Nortrel (21 Day Regimen)Barr Laboratories Inc.
Nortrel (28 Day Regimen)Barr Laboratories Inc.
Nortrel 7/7/7 (28 Day Regimen)Barr Laboratories Inc.
Novo-cyproterone/ethinyl EstradiolTeva Canada Limited
NuvaringOrganon USA Inc.
OcellaBarr Laboratories, Inc.
OrsythiaQualitest Pharmaceuticals
Ortho 0.5/35 Tablets (21 Day)Janssen Inc
Ortho 0.5/35 Tablets (28 Day)Janssen Inc
Ortho 1/35 Tablets (21 Day)Janssen Inc
Ortho 1/35 Tablets (28 Day)Janssen Inc
Ortho 10/11 Tablets (21 Day)Janssen Inc
Ortho 10/11 Tablets (28 Day)Janssen Inc
Ortho 7/7/7 Tablets (21 Day)Janssen Inc
Ortho 7/7/7 Tablets (28 Day)Janssen Inc
Ortho CeptJanssen Pharmaceuticals, Inc.
Ortho CyclenJanssen Pharmaceuticals, Inc.
Ortho EvraJanssen Pharmaceutical, Inc.
Ortho Novum 135Janssen Pharmaceuticals, Inc.
Ortho Tri CyclenJanssen Pharmaceuticals, Inc.
Ortho Tri Cyclen LoJanssen Pharmaceuticals, Inc.
Ortho-cept Tablets (21 Day)Janssen Inc
Ortho-cept Tablets (28 Day)Janssen Inc
Ortho-novum 777A S Medication Solutions Llc
Ovcon 35Warner Chilcott (US), LLC
Ovima 21Apotex Inc
Ovima 28Apotex Inc
Ovral 21Pfizer Canada Inc
Ovral 21 TabWyeth Ltd.
Ovral 28 TabletsWyeth Canada
Ovral 28tabWyeth Ltd.
Pirmella 1/35Lupin Pharmaceuticals, Inc.
Pirmella 7/7/7Lupin Pharmaceuticals, Inc.
PortiaBarr Laboratories Inc.
Portia 21Teva Canada Limited
Portia 28Teva Canada Limited
Preven Emergency ContraceptiveGynÉtics Ltd/LtÉe
Preven TabletsShire Pharma Canada Ulc
PrevifemQualitest Pharmaceuticals
Previfem (21day)Novopharm Limited
Previfem (28day)Novopharm Limited
Qismette 21LUPIN LIMITED
Qismette 28LUPIN LIMITED
QuasenseWatson Pharma, Inc.
Ran-cyproterone/ethinyl EstradiolRanbaxy Pharmaceuticals Canada Inc.
ReclipsenWatson Pharma, Inc.
Reclipsen 21Actavis Pharma Company
Reclipsen 28Actavis Pharma Company
Sarensis 21Patriot A Division Of Janssen Inc
Sarensis 28Patriot A Division Of Janssen Inc
SeasonaleTeva Women's Health Inc
SeasoniqueTeva Women's Health Inc
Select 1/35 (21-day)Pfizer Canada Inc
Select 1/35 (28-day)Pfizer Canada Inc
SetlakinNorthstar Rx LLC
SprintecBarr Laboratories Inc.
SronyxWatson Pharma, Inc.
SyedaSandoz Inc
Synphasic 21 TabletsPfizer Canada Inc
Synphasic 28 TabletsPfizer Canada Inc
Synphasic-28 TabletsSyntex Inc.
Tarina Fe 1/20Afaxys Inc.
Tilia FeRebel Distributors Corp
Tri-cyclen Lo (-21 Day)Janssen Inc
Tri-cyclen Lo (28 Day)Janssen Inc
Tri-cyclen Tablets - 21-dayJanssen Inc
Tri-cyclen Tablets - 28-dayJanssen Inc
Tri-estaryllaSandoz Inc
Tri-legest Fe 28 DayBarr Laboratories Inc.
Tri-lena 21Actavis Pharma Company
Tri-lena 28Actavis Pharma Company
Tri-lena Lo 21Actavis Pharma Company
Tri-lena Lo 28Actavis Pharma Company
Tri-linyahNorthstar Rx LLC
Tri-LO- EstaryllaSandoz Inc
Tri-LO-marziaLupin Pharmaceuticals, Inc.
Tri-LO-sprintecTeva Pharmaceuticals USA Inc
Tri-norinylActavis Pharma, Inc.
Tri-previfemQualitest Pharmaceuticals
Tri-previfem (21 Day)Novopharm Limited
Tri-previfem (28 Day)Novopharm Limited
Tri-sprintecBarr Laboratories Inc.
Tricira LoApotex Inc
TrinessaRebel Distributors Corp
Trinessa LoActavis Pharma, Inc.
Triphasil 21Wyeth Canada
Triphasil 21 TabWyeth Ltd.
Triphasil 28Wyeth Canada
Triphasil 28 TabWyeth Ltd.
Triquilar 21Bayer Inc
Triquilar 28Bayer Inc
Velivet Triphasic RegimenBarr Laboratories Inc.
VesturaWatson Pharma, Inc.
Vienva TmSandoz Inc
VyfemlaLupin Pharmaceuticals, Inc.
WeraNorthstar Rx LLC
Wymzya FeLupin Pharmaceuticals, Inc.
XulaneMylan Pharmaceuticals Inc.
YasminBayer Health Care Pharmaceuticals Inc.
Yasmin 21Bayer Inc
Yasmin 28Bayer Inc
Yasmin PlusBayer Inc
YazBayer Health Care Pharmaceuticals Inc.
Yaz PlusBayer Inc
Zamine 21Apotex Inc
Zamine 28Apotex Inc
ZarahWatson Pharma, Inc.
Zarah 21Cobalt Pharmaceuticals Company
Zarah 28Cobalt Pharmaceuticals Company
ZenchentWatson Pharma, Inc.
Zenchent FeWatson Pharma, Inc.
ZeosaTeva Pharmaceuticals USA Inc
Zovia 1/35e-28Actavis Pharma, Inc.
Zovia 1/50e-28Actavis Pharma, Inc.
SaltsNot Available
Categories
UNII423D2T571U
CAS number57-63-6
WeightAverage: 296.4034
Monoisotopic: 296.177630012
Chemical FormulaC20H24O2
InChI KeyInChIKey=BFPYWIDHMRZLRN-RHKZOZTBNA-N
InChI
InChI=1/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+/s2
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][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 17-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Phenanthrene
  • Tetralin
  • Benzenoid
  • Ynone
  • Tertiary alcohol
  • Cyclic alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFor 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.
PharmacodynamicsEthinyl 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 actionEstrogens 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).
Related Articles
AbsorptionRapid and complete absorption follows oral intake of ethinyl estradiol (bioavailability 43%).
Volume of distributionNot Available
Protein binding97%
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.

SubstrateEnzymesProduct
Ethinyl Estradiol
2β-OH-17β-ethinylestradiolDetails
Route of eliminationNot Available
Half life36 +/- 13 hours
ClearanceNot Available
ToxicityOral, 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
Manufacturers
  • Schering corp sub schering plough corp
  • Pharmacia and upjohn co
  • Organon usa inc
Packagers
Dosage forms
FormRouteStrength
Kit
Tabletoral.05 mg
Tabletoral.5 mg
Tabletoral.02 mg
Patch (extended release)transdermal
Tablet (chewable)oral
Tablet, film coatedoral
Tabletoral
Insert, extended releasevaginal
Ring (slow-release)vaginal
Kitoral
Patch, extended releasetransdermal
Patchtransdermal
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)
US5798338 No1995-07-102015-07-10Us
US5876746 No1995-11-202015-11-20Us
US5898032 No1997-06-232017-06-23Us
US5989581 No1998-04-082018-04-08Us
US6156742 No2000-12-052020-12-05Us
US6214815 Yes1999-12-092019-12-09Us
US6441168 No2002-07-302022-07-30Us
US6500814 No1998-09-032018-09-03Us
US6652880 No2000-03-292020-03-29Us
US6667050 No1999-04-062019-04-06Us
US6787531 No2000-08-312020-08-31Us
US6933395 No1997-08-112017-08-11Us
US6958326 No2001-12-202021-12-20Us
US6987101 No1997-12-222017-12-22Us
US7163931 No2001-12-202021-12-20Us
US7320969 No2004-01-302024-01-30Us
US7615545 No2003-06-152023-06-15Us
US7704984 No2009-02-022029-02-02Us
US7855190 No2008-12-052028-12-05Us
US7858605 No2003-06-232023-06-23Us
US8415332 No2009-03-112029-03-11Us
US8450299 No2005-10-072025-10-07Us
US8617597 No2010-02-082030-02-08Us
USRE39861 No1997-06-232017-06-23Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point142-144Inhoffen, 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (9.42 KB)
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000b-0290000000-0ef72fb5e00440b9ff50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-0960000000-945d82a0ab94f246ac88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-056s-2910000000-0d38daebb87a39304e91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-03di-0890000000-7a166e952207cf7bc1d3View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03dj-2980000000-831c8190c59f98fc8623View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot 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 ReferencesNot Available
External Links
ATC CodesG03AA01G03AA02G03AA03G03AA04G03AA05G03AA06G03AA07G03AA08G03AA09G03AA10G03AA11G03AA12G03AA13G03AA15G03AA16G03AB01G03AB02G03AB03G03AB04G03AB05G03AB06G03AB07G03CA01L02AA03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (470 KB)
MSDSDownload (73.9 KB)
Interactions
Drug Interactions
Drug
AbciximabEthinyl Estradiol may decrease the anticoagulant activities of Abciximab.
AcenocoumarolEthinyl Estradiol may decrease the anticoagulant activities of Acenocoumarol.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Ethinyl Estradiol.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Ethinyl Estradiol.
Anthrax immune globulinEthinyl Estradiol may increase the thrombogenic activities of Anthrax immune globulin.
BatimastatThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Batimastat.
BexaroteneThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Bexarotene.
BortezomibThe metabolism of Bortezomib can be decreased when combined with Ethinyl Estradiol.
ButabarbitalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Butabarbital.
ButethalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Butethal.
C1 Esterase Inhibitor (Human)Ethinyl Estradiol may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Ethinyl Estradiol.
CapromabEthinyl Estradiol may decrease effectiveness of Capromab as a diagnostic agent.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Ethinyl Estradiol.
Citric AcidEthinyl Estradiol may decrease the anticoagulant activities of Citric Acid.
ColesevelamThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Colesevelam.
DalteparinEthinyl Estradiol may decrease the anticoagulant activities of Dalteparin.
DicoumarolEthinyl Estradiol may decrease the anticoagulant activities of Dicoumarol.
Edetic AcidEthinyl Estradiol may decrease the anticoagulant activities of Edetic Acid.
EnoxaparinEthinyl Estradiol may decrease the anticoagulant activities of Enoxaparin.
Eslicarbazepine acetateThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Eslicarbazepine acetate.
Ethyl biscoumacetateEthinyl Estradiol may decrease the anticoagulant activities of Ethyl biscoumacetate.
FludrocortisoneThe serum concentration of Fludrocortisone can be increased when it is combined with Ethinyl Estradiol.
FluvoxamineThe metabolism of Fluvoxamine can be decreased when combined with Ethinyl Estradiol.
Fondaparinux sodiumEthinyl Estradiol may decrease the anticoagulant activities of Fondaparinux sodium.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Ethinyl Estradiol.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Ethinyl Estradiol.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Ethinyl Estradiol.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Ethinyl Estradiol.
HeparinEthinyl Estradiol may decrease the anticoagulant activities of Heparin.
HeptabarbitalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Heptabarbital.
HexobarbitalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Hexobarbital.
IcosapentIcosapent may increase the thrombogenic activities of Ethinyl Estradiol.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Ethinyl Estradiol.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Ethinyl Estradiol.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Ethinyl Estradiol.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Ethinyl Estradiol.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Ethinyl Estradiol.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Ethinyl Estradiol.
IsoflurophateThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Isoflurophate.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Ethinyl Estradiol.
LiothyronineThe therapeutic efficacy of Liothyronine can be decreased when used in combination with Ethinyl Estradiol.
LumacaftorThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Lumacaftor.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Ethinyl Estradiol.
MethohexitalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Methohexital.
PentobarbitalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Pentobarbital.
PhenindioneEthinyl Estradiol may decrease the anticoagulant activities of Phenindione.
PhenprocoumonEthinyl Estradiol may decrease the anticoagulant activities of Phenprocoumon.
PhenytoinThe metabolism of Ethinyl Estradiol can be increased when combined with Phenytoin.
PrimidoneThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Primidone.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Ethinyl Estradiol.
RifabutinThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Rifabutin.
RufinamideThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Rufinamide.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Ethinyl Estradiol.
SecobarbitalThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with Secobarbital.
SimeprevirThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Simeprevir.
St. John's WortThe therapeutic efficacy of Ethinyl Estradiol can be decreased when used in combination with St. John's Wort.
SulodexideEthinyl Estradiol may decrease the anticoagulant activities of Sulodexide.
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Ethinyl Estradiol.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Ethinyl Estradiol.
TreprostinilEthinyl Estradiol may decrease the anticoagulant activities of Treprostinil.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Ethinyl Estradiol.
Vitamin CThe serum concentration of Ethinyl Estradiol can be increased when it is combined with Vitamin C.
WarfarinEthinyl Estradiol may decrease the anticoagulant activities of Warfarin.
Food InteractionsNot Available

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. 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 and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and is...
Gene Name:
NR1I2
Uniprot ID:
O75469
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 ]

Enzymes

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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
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
inhibitorinducer
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
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 presence of sodium.(Microbial infection) Acts as a receptor for hepatitis B virus.
Gene Name:
SLC10A1
Uniprot ID:
Q14973
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
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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on July 24, 2016 03:07