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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
SynonymLanguageCode
17 alpha-EthinylestradiolNot AvailableNot Available
17 alpha-EthynylestradiolNot AvailableNot Available
17 alpha-EthynyloestradiolNot AvailableNot Available
17-ethinyl-3,17-estradiolNot AvailableNot Available
17-ethinyl-3,17-oestradiolNot AvailableNot Available
17-ethinylestradiolNot AvailableNot Available
17alpha-Ethinyl estradiolNot AvailableNot Available
17α-ethynylestradiolNot AvailableNot Available
Ethinyl-OestranolNot AvailableNot Available
EthinylestradiolNot AvailableNot Available
EthinylestradiolumLatinINN
EthinylestriolNot AvailableNot Available
EthinyloestradiolNot AvailableNot Available
Ethynyl estradiolNot AvailableNot Available
EthynylestradiolNot AvailableNot Available
EthynyloestradiolNot AvailableNot Available
EtinilestradiolSpanishINN
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
EstinylSchering
Brand mixtures
Brand NameIngredients
AlesseEthinyl Estradiol + Levonorgestrel
AmethystLevonorgestrel + Ethinyl Estradiol
ApriEthinyl Estradiol + desogestrel
AvianeEthinyl Estradiol + Levonorgestrel
BreviconEthinyl Estradiol + Norethindrone
CyclenEthinyl Estradiol + Norgestimate
DemulenEthinyl Estradiol + Ethynodiol Diacetate
DesogenEthinyl Estradiol + desogestrel
Diane-35Cyproterone Acetate + Ethinyl Estradiol
EvraEthinyl Estradiol + Norelgestromin
femhrtNorethindrone + Ethinyl Estradiol
Femhrt 1/5Ethinyl Estradiol + Norethindrone Acetate
FemodeneEthinyl Estradiol + gestodene
FemodetteEthinyl Estradiol + gestodene
JINTELINorethindrone + Ethinyl Estradiol
JolessaEthinyl Estradiol + Levonorgestrel
Junelnorethindrone acetate+ Ethinyl Estradiol
KarivaEthinyl Estradiol + desogestrel
LessinaEthinyl Estradiol + Levonorgestrel
Lo MinastrinNorethindrone acetate, ethinyl estradiol, ferrous fumarate
Lo-FemenalEthinyl Estradiol + Norgestrel
LoestrinEthinyl Estradiol + Norethindrone Acetate
LuteraEthinyl Estradiol + Levonorgestrel
LybrelEthinyl Estradiol + Levonorgestrel
MarvelonDesogestrel + Ethinyl Estradiol
MercilonEthinyl Estradiol + desogestrel
Microgestinnorethindrone acetate+ Ethinyl Estradiol
Min-OvralEthinyl Estradiol + Levonorgestrel
Minestrin 1/20Ethinyl Estradiol + Norethindrone Acetate
MinuletEthinyl Estradiol + gestodene
MircetteEthinyl Estradiol + desogestrel
Neo Mens TabEthinyl Estradiol + Ethisterone
NuvaringEthinyl Estradiol + Etonogestrel
OcellaDrospirenone + Ethinyl Estradiol
OrthoEthinyl Estradiol + Norethindrone
Ortho-CeptDesogestrel + Ethinyl Estradiol
OvconEthinyl Estradiol + Norethindrone
OvralEthinyl Estradiol + Norgestrel
PrevenEthinyl Estradiol + Levonorgestrel
QuartetteLevonorgestrel/Ethinyl Estradiol + Ethinyl Estradiol
QuasenseEthinyl Estradiol + Levonorgestrel
SeasonaleEthinyl Estradiol + Levonorgestrel
SeasoniqueEthinyl Estradiol + Levonorgestrel
Select 1/35Ethinyl Estradiol + Norethindrone
SronyxEthinyl Estradiol + Levonorgestrel
SynphasicEthinyl Estradiol + Norethindrone
Tri-CyclenEthinyl Estradiol + Norgestimate
Tri-Cyclen LoEthinyl Estradiol + Norgestimate
TriphasilEthinyl Estradiol + Levonorgestrel
TriquilarEthinyl Estradiol + Levonorgestrel
YasminDrospirenone + Ethinyl Estradiol
YasminelleDrospirenone + Ethinyl Estradiol
YazDrospirenone + Ethinyl Estradiol
ZarahDrospirenone + Ethinyl Estradiol
SaltsNot Available
Categories
CAS number57-63-6
WeightAverage: 296.4034
Monoisotopic: 296.177630012
Chemical FormulaC20H24O2
InChI KeyBFPYWIDHMRZLRN-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).
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 substrateNon-inhibitor0.9186
CYP450 2D6 substrateNon-inhibitor0.9506
CYP450 2C19 substrateNon-inhibitor0.6641
CYP450 3A4 substrateInhibitor0.5224
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
Pharmacoeconomics
Manufacturers
  • Schering corp sub schering plough corp
  • Pharmacia and upjohn co
  • Organon usa inc
Packagers
Dosage formsNot Available
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.
PatentsNot Available
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)
SpectraNot 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 Reference
  1. FDA label.
External Links
ATC CodesG03CA01L02AA03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (470 KB)
MSDSDownload (73.9 KB)
Interactions
Drug Interactions
Drug
AbciximabEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
AcenocoumarolEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
AcetohexamideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
AgomelatineCYP1A2 Inhibitors (Moderate) may increase the serum concentration of Agomelatine.
AlogliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
AminoglutethimideMay increase the metabolism of Progestins.
AnastrozoleEstrogen Derivatives may diminish the therapeutic effect of Anastrozole.
AprepitantMay decrease the serum concentration of Contraceptives (Estrogens).
AripiprazoleCYP3A4 Inhibitors (Weak) may increase the serum concentration of ARIPiprazole.
armodafinilMay decrease the serum concentration of Contraceptives (Estrogens).
ArtemetherMay decrease the serum concentration of Contraceptives (Estrogens).
BatimastatMay decrease the serum concentration of Contraceptives (Estrogens).
BoceprevirMay decrease the serum concentration of Contraceptives (Estrogens).
BosentanMay decrease the serum concentration of Contraceptives (Estrogens).
ButabarbitalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
ButethalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
CanagliflozinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
CarbamazepineMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
ChlorpropamideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Citric AcidEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
ClobazamMay decrease the serum concentration of Contraceptives (Estrogens).
ColesevelamColesevelam may decrease the serum concentration of Ethinyl Estradiol.
ConivaptanMay increase the serum concentration of CYP3A4 Substrates.
DabrafenibMay decrease the serum concentration of CYP3A4 Substrates.
DalteparinEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
DasatinibMay increase the serum concentration of CYP3A4 Substrates.
DeferasiroxMay decrease the serum concentration of CYP3A4 Substrates.
DehydroepiandrosteroneMay enhance the adverse/toxic effect of Estrogen Derivatives.
DicoumarolEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
DofetilideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Dofetilide.
Edetic AcidEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
EnoxaparinEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
Ethyl biscoumacetateEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
ExemestaneEstrogen Derivatives may diminish the therapeutic effect of Exemestane.
ExenatideMay decrease the serum concentration of Contraceptives (Estrogens).
FelbamateMay decrease the serum concentration of Contraceptives (Estrogens). Contraceptive failure is possible.
Fondaparinux sodiumEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
FosaprepitantMay decrease the serum concentration of Contraceptives (Estrogens). The active metabolite aprepitant is likely responsible for this effect.
FosphenytoinMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
GliclazideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GlimepirideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GliquidoneHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GlyburideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
GriseofulvinMay increase the metabolism of Contraceptives (Estrogens). Contraceptive failure is possible.
HeparinEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
HeptabarbitalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
HexobarbitalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
HyaluronidaseEstrogen Derivatives may diminish the therapeutic effect of Hyaluronidase.
HydrocodoneCYP3A4 Inhibitors (Weak) may increase the serum concentration of Hydrocodone.
Insulin AspartHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin DetemirHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin GlargineHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin GlulisineHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin LisproHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin RegularHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Insulin, isophaneHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
IsoflurophateMay decrease the serum concentration of Contraceptives (Estrogens).
IvacaftorMay increase the serum concentration of CYP3A4 Substrates.
LamotrigineContraceptives (Estrogens) may decrease the serum concentration of LamoTRIgine.
LenalidomideEstrogen Derivatives may enhance the thrombogenic effect of Lenalidomide.
LinagliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
LomitapideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Lomitapide.
LULICONAZOLEMay increase the serum concentration of CYP3A4 Substrates.
MetforminHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
MethohexitalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
MetreleptinMay decrease the serum concentration of Contraceptives (Estrogens). Metreleptin may increase the serum concentration of Contraceptives (Estrogens).
MifepristoneMay diminish the therapeutic effect of Contraceptives (Estrogens). Mifepristone may increase the serum concentration of Contraceptives (Estrogens).
MitotaneMay decrease the serum concentration of CYP3A4 Substrates.
ModafinilMay decrease the serum concentration of Contraceptives (Estrogens).
NafcillinMay increase the metabolism of Contraceptives (Estrogens).
NevirapineMay decrease the serum concentration of Contraceptives (Estrogens).
OspemifeneEstrogen Derivatives may enhance the adverse/toxic effect of Ospemifene. Estrogen Derivatives may diminish the therapeutic effect of Ospemifene.
OxcarbazepineMay decrease the serum concentration of Contraceptives (Estrogens). Contraceptive failure is possible.
PentobarbitalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
PhenindioneEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
PhenprocoumonEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
PhenytoinMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
PimozideCYP3A4 Inhibitors (Weak) may increase the serum concentration of Pimozide.
PirfenidoneCYP1A2 Inhibitors (Moderate) may increase the serum concentration of Pirfenidone.
PrimidoneMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
prucaloprideMay decrease the serum concentration of Contraceptives (Estrogens).
RepaglinideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
RopiniroleEstrogen Derivatives may increase the serum concentration of ROPINIRole.
RufinamideMay decrease the serum concentration of Ethinyl Estradiol.
SaxagliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
SecobarbitalMay diminish the therapeutic effect of Contraceptives (Estrogens). Contraceptive failure is possible.
SelegilineContraceptives (Estrogens) may increase the serum concentration of Selegiline.
SiltuximabMay decrease the serum concentration of CYP3A4 Substrates.
SimeprevirMay decrease the serum concentration of Contraceptives (Estrogens).
SulodexideEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
TelaprevirMay decrease the serum concentration of Contraceptives (Estrogens).
ThalidomideContraceptives (Estrogens) may enhance the thrombogenic effect of Thalidomide.
TipranavirEstrogen Derivatives may enhance the dermatologic adverse effect of Tipranavir. The combination of tipranavir/ritonavir and ethinyl estradiol/norethindrone was associated with a high incidence of skin rash. Tipranavir may decrease the serum concentration of Estrogen Derivatives.
TizanidineContraceptives (Estrogens) may increase the serum concentration of TiZANidine.
TocilizumabMay decrease the serum concentration of CYP3A4 Substrates.
TolbutamideHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
TopiramateMay decrease the serum concentration of Contraceptives (Estrogens). Contraceptive failure is possible.
Tranexamic AcidContraceptives (Estrogens) may enhance the thrombogenic effect of Tranexamic Acid.
TreprostinilEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
UlipristalMay diminish the therapeutic effect of Progestins. Progestins may diminish the therapeutic effect of Ulipristal.
VildagliptinHyperglycemia-Associated Agents may diminish the therapeutic effect of Antidiabetic Agents.
Vitamin CMay increase the serum concentration of Estrogen Derivatives.
WarfarinEstrogen Derivatives may diminish the anticoagulant effect of Anticoagulants. More specifically, the potential prothrombotic effects of some estrogens and progestin-estrogen combinations may counteract anticoagulant effects.
Food InteractionsNot Available

Targets

1. Estrogen receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Estrogen receptor P03372 Details

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
  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
  3. Brama M, Gnessi L, Basciani S, Cerulli N, Politi L, Spera G, Mariani S, Cherubini S, d’Abusco AS, 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
  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
  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
  6. Notch EG, Mayer GD: 17alpha-Ethinylestradiol hinders nucleotide excision repair in zebrafish liver cells. Aquat Toxicol. 2009 Dec 13;95(4):273-8. Epub 2009 Jan 23. Pubmed
  7. Bennink HJ: Reprint of Are all estrogens the same? Maturitas. 2008 Sep-Oct;61(1-2):195-201. Pubmed
  8. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Nuclear receptor subfamily 1 group I member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Nuclear receptor subfamily 1 group I member 2 O75469 Details

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

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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

2. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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

Transporters

1. Bile salt export pump

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor inducer

Components

Name UniProt ID Details
Bile salt export pump O95342 Details

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
  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

2. Sodium/bile acid cotransporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Sodium/bile acid cotransporter Q14973 Details

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

3. Canalicular multispecific organic anion transporter 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Canalicular multispecific organic anion transporter 1 Q92887 Details

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
  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

4. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

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

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Drug created on June 13, 2005 07:24 / Updated on October 29, 2013 15:35