Identification

Name
Ethinylestradiol
Accession Number
DB00977
Description

Ethinylestradiol was first synthesized in 1938 by Hans Herloff Inhoffen and Walter Hohlweg at Schering.1 It was developed in an effort to create an estrogen with greater oral bioavailability.1 These properties were achieved by the substitution of an ethinyl group at carbon 17 of estradiol.1 Ethinylestradiol soon replaced mestranol in contraceptive pills.1

Ethinylestradiol was granted FDA approval on 25 June 1943.14

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 296.4034
Monoisotopic: 296.177630012
Chemical Formula
C20H24O2
Synonyms
  • 17-ethinyl-3,17-estradiol
  • 17-ethinyl-3,17-oestradiol
  • 17-ethinylestradiol
  • 17alpha-Ethinyl estradiol
  • 17α-ethynylestradiol
  • Ethinyl estradiol
  • Ethinylestradiol
  • Ethinylestradiolum
  • Ethinyloestradiol
  • Ethynyl estradiol
  • Etinilestradiol
External IDs
  • NSC-10973

Pharmacology

Indication

Ethinylestradiol is combined with other drugs for use as a contraceptive, premenstrual dysphoric disorder, moderate acne, moderate to severe vasomotor symptoms of menopause, prevention of postmenopausal osteoporosis.15,25,16,17,24,18,19,20,21,22,23

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Ethinylestradiol is a synthetic estrogen that decreases luteinizing hormone to decrease endometrial vascularization, and decreases gonadotrophic hormone to prevent ovulation.13,12,15 It has a long duration of action as it is taken once daily, and a wide therapeutic index as overdoses are generally not associated with serious adverse effects.15 Patients should be counselled regarding the risks of thrombotic events.15

Mechanism of action

Ethinylestradiol is a synthetic estrogenic compound.15 Use of estrogens have a number of effects on the body including reduced bone density.11 Combined oral contraceptives suppress ovulation by suppressing gonadotrophic hormone, thickening cervical mucus to prevent the travel of sperm, and preventing changes in the endometrium required for implantation of a fertilized egg.12,15 Ethinylestradiol decreases luteinizing hormone, decreasing vascularity in the endometrium.13 It also increases sex hormone binding globulin.13

TargetActionsOrganism
AEstrogen receptor alpha
agonist
Humans
UNuclear receptor subfamily 1 group I member 2
agonist
Humans
Absorption

A 30µg oral dose of ethinylestradiol reaches a Cmax of 74.1±35.6pg/mL, with a Tmax of 1.5±0.5h, and an AUC of 487.4±166.6pg*h/mL.10 A 1.2mg dose delivered via a patch reaches a Cmax of 28.8±10.3pg/mL, with a Tmax of 86±31h, and an AUC of3895±1423pg*h/mL.10

Volume of distribution

A 30µg oral dose has an apparent volume of distribution of 625.3±228.7L and a 1.2mg topical dose has an apparent volume of distribution of 11745.3±15934.8L.10

Protein binding

Enthinylestradiol is 98.3-98.5% bound to albumin in serum8 but also exhibits binding to sex hormone binding globulin.9

Metabolism

Ethinylestradiol can be glucuronidated by UGT1A1, UGT1A3, UGT1A4, UGT1A9, and UGT2B7.3,7 Ethinylestradiol is also sulfated by SULT1A1, SULT1A3, and SULT1E1.6,7 Ethinylestradiol can also be hydroxylated at positions 2, 4, 6, 7, and 165,7 by CYP3A4, CYP3A5, CYP2C8, CYP2C9, and CYP1A2.7 These hydroxylated metabolites can be methylated by catechol-O-methyltransferase.7 The methoxy metabolites can in turn be sulfated or glucuronidated.7

Hover over products below to view reaction partners

Route of elimination

Ethinylestradiol is 59.2% eliminated in the urine and bile, while 2-3% is eliminated in the feces.2 Over 90% of ethinylestradiol is eliminated as the unchanged parent drug.2

Half-life

A 30µg oral dose has a half life of 8.4±4.8h and a 1.2mg topical dose has a half life of 27.7±34.2h.10

Clearance

Ethinylestradiol has an intravenous clearance of 16.47L/h, and an estimated renal clearance of approximately 2.1L/h.4 A 30µg oral dose has a clearance of 58.0±19.8L/h and a 1.2mg topical dose has a clearance of 303.5±100.5L/h.10

Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Female patients experiencing and overdose may present with withdrawal bleeding, nausea, vomiting, breast tenderness, abdominal pain, drowsiness, and fatigue.15,25,16,17,24,18,19,20,21,22,23 Overdose should be treated with symptomatic and supportive care including monitoring for potassium concentrations, sodium concentrations, and signs of metabolic acidosis.15,25,16,17,24,18,19,20,21,22,23

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

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirThe metabolism of Abacavir can be increased when combined with Ethinylestradiol.
AbametapirThe serum concentration of Ethinylestradiol can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Ethinylestradiol can be increased when combined with Abatacept.
AbciximabEthinylestradiol may decrease the anticoagulant activities of Abciximab.
AbirateroneThe serum concentration of Ethinylestradiol can be increased when it is combined with Abiraterone.
AcalabrutinibThe metabolism of Ethinylestradiol can be decreased when combined with Acalabrutinib.
AcarboseThe therapeutic efficacy of Acarbose can be decreased when used in combination with Ethinylestradiol.
AceclofenacAceclofenac may increase the thrombogenic activities of Ethinylestradiol.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Ethinylestradiol.
AcetaminophenThe serum concentration of Acetaminophen can be decreased when it is combined with Ethinylestradiol.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Avoid St. John's Wort. St. John's Wort may decrease the effectiveness of ethinylestradiol.

Products

Active Moieties
NameKindUNIICASInChI Key
Estradiolunknown4TI98Z838E50-28-2VOXZDWNPVJITMN-ZBRFXRBCSA-N
Product Images
International/Other Brands
Estinyl (Schering)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Estinyl Tab 0.05mgTabletOralSchering Plough1951-12-312000-07-11Canada flag
Estinyl Tab 0.5mgTabletOralSchering Plough1951-12-312000-07-11Canada flag
Estinyl Tablets 0.02 Mg.TabletOralSchering Plough1951-12-311998-11-17Canada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AfirmelleEthinylestradiol (0.02 mg/1) + Levonorgestrel (0.1 mg/1)OralAurobindo Pharma Limited2019-05-31Not applicableUS flag
Alesse 21Ethinylestradiol (20 mcg) + Levonorgestrel (100 mcg)TabletOralPfizer Canada Ulc1998-01-07Not applicableCanada flag
Alesse 28Ethinylestradiol (0.02 mg/1) + Levonorgestrel (0.1 mg/1)KitOralWyeth Pharmaceuticals Inc., a subsidiary of Pfizer Inc.1997-04-012008-02-29US flag
Alesse 28Ethinylestradiol (20 mcg) + Levonorgestrel (100 mcg)TabletOralPfizer Canada Ulc1998-01-07Not applicableCanada flag
AltaveraEthinylestradiol (0.03 mg/1) + Levonorgestrel (0.15 mg/1)OralXiromed, Llc.2018-01-01Not applicableUS flag
AltaveraEthinylestradiol (0.03 mg/1) + Levonorgestrel (0.15 mg/1)OralSandoz Inc2010-08-032019-08-31US flag
Alyacen 1/35Ethinylestradiol (0.035 mg/1) + Norethisterone (1 mg/1)KitOralGlenmark Pharmaceuticals Inc.,Usa2012-01-19Not applicableUS flag
Alyacen 1/35Ethinylestradiol (0.035 mg/1) + Norethisterone (1 mg/1)OralA-S Medication Solutions2012-01-19Not applicableUS flag
Alyacen 1/35Ethinylestradiol (0.035 mg/1) + Norethisterone (1 mg/1)OralREMEDYREPACK INC.2018-05-162020-03-26US flag
Alyacen 7/7/7Ethinylestradiol (0.035 mg/1) + Ethinylestradiol (0.035 mg/1) + Ethinylestradiol (0.035 mg/1) + Norethisterone (0.5 mg/1) + Norethisterone (0.75 mg/1) + Norethisterone (1 mg/1)KitOralGlenmark Pharmaceuticals Inc.,Usa2012-01-19Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
FalessaEthinylestradiol (0.02 mg/1) + Folic acid (1 mg/1) + Levonorgestrel (0.1 mg/1)KitOralAvion Pharmaceuticals, Llc2014-02-17Not applicableUS flag
MercilonEthinylestradiol (0.02 mg/1) + Desogestrel (0.15 mg/1)TabletOralOASIS TRADING2018-11-22Not applicableUS flag
Minivlar 30Ethinylestradiol (0.03 mg/1) + Levonorgestrel (0.15 mg/1)TabletOralOASIS TRADING2018-11-21Not applicableUS flag
MyvlarEthinylestradiol (0.03 mg/1) + Gestodene (0.075 mg/1)TabletOralOASIS TRADING2018-11-22Not applicableUS flag

Categories

ATC Codes
G03AA15 — Chlormadinone and ethinylestradiolG03AA11 — Norgestimate and ethinylestradiolL02AA03 — EthinylestradiolG03AA12 — Drospirenone and ethinylestradiolG03AA16 — Dienogest and ethinylestradiolG03AB02 — Lynestrenol and ethinylestradiolG03CA01 — EthinylestradiolG03AA03 — Lynestrenol and ethinylestradiolG03AA10 — Gestodene and ethinylestradiolG03AB04 — Norethisterone and ethinylestradiolG03AB01 — Megestrol and ethinylestradiolG03AB07 — Chlormadinone and ethinylestradiolG03AA13 — Norelgestromin and ethinylestradiolG03AA06 — Norgestrel and ethinylestradiolG03AA08 — Medroxyprogesterone and ethinylestradiolG03AA02 — Quingestanol and ethinylestradiolG03AA04 — Megestrol and ethinylestradiolG03AA09 — Desogestrel and ethinylestradiolG03AB09 — Norgestimate and ethinylestradiolG03AA07 — Levonorgestrel and ethinylestradiolG03AB03 — Levonorgestrel and ethinylestradiolG03AA05 — Norethisterone and ethinylestradiolG03AB05 — Desogestrel and ethinylestradiolG03AB06 — Gestodene and ethinylestradiolG03AA01 — Etynodiol and ethinylestradiol
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1-hydroxy-2-unsubstituted benzenoid / 17-hydroxysteroid / 3-hydroxysteroid / Acetylide / Alcohol / Aromatic homopolycyclic compound / Benzenoid / Cyclic alcohol / Estrogen-skeleton / Hydrocarbon derivative
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)

Chemical Identifiers

UNII
423D2T571U
CAS number
57-63-6
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

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
  1. Dhont M: History of oral contraception. Eur J Contracept Reprod Health Care. 2010 Dec;15 Suppl 2:S12-8. doi: 10.3109/13625187.2010.513071. [PubMed:21091163]
  2. Cargill DI, Steinetz BG, Gosnell E, Beach VL, Meli A, Fujimoto GI, Reynolds BM: Fate of ingested radiolabeled ethynylestradiol and its 3-cyclopentyl ether in patients with bile fistulas. J Clin Endocrinol Metab. 1969 Aug;29(8):1051-61. doi: 10.1210/jcem-29-8-1051. [PubMed:5802625]
  3. Ebner T, Remmel RP, Burchell B: Human bilirubin UDP-glucuronosyltransferase catalyzes the glucuronidation of ethinylestradiol. Mol Pharmacol. 1993 Apr;43(4):649-54. [PubMed:8474433]
  4. Ezuruike U, Humphries H, Dickins M, Neuhoff S, Gardner I, Rowland Yeo K: Risk-Benefit Assessment of Ethinylestradiol Using a Physiologically Based Pharmacokinetic Modeling Approach. Clin Pharmacol Ther. 2018 Dec;104(6):1229-1239. doi: 10.1002/cpt.1085. Epub 2018 Apr 27. [PubMed:29637542]
  5. Bolt HM, Kappus H, Kasbohrer R: Metabolism of 17 alpha-ethinylestradiol by human liver microsomes in vitro: aromatic hydroxylation and irreversible protein binding of metabolites. J Clin Endocrinol Metab. 1974 Dec;39(6):1072-80. doi: 10.1210/jcem-39-6-1072. [PubMed:4214831]
  6. Schrag ML, Cui D, Rushmore TH, Shou M, Ma B, Rodrigues AD: Sulfotransferase 1E1 is a low km isoform mediating the 3-O-sulfation of ethinyl estradiol. Drug Metab Dispos. 2004 Nov;32(11):1299-303. doi: 10.1124/dmd.32.11.. [PubMed:15483196]
  7. Stegeman BH, Vos HL, Helmerhorst FM, Rosendaal FR, Reitsma PH, van Hylckama Vlieg A: Genetic variation in the first-pass metabolism of ethinylestradiol, sex hormone binding globulin levels and venous thrombosis risk. Eur J Intern Med. 2017 Jul;42:54-60. doi: 10.1016/j.ejim.2017.05.019. Epub 2017 Jun 1. [PubMed:28579309]
  8. Kuhnz W, Pfeffer M, al-Yacoub G: Protein binding of the contraceptive steroids gestodene, 3-keto-desogestrel and ethinylestradiol in human serum. J Steroid Biochem. 1990 Feb;35(2):313-8. doi: 10.1016/0022-4731(90)90290-9. [PubMed:2308344]
  9. 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]
  10. Zhang C, Li H, Xiong X, Zhai S, Wei Y, Zhang S, Zhang Y, Xu L, Liu L: An open-label, two-period comparative study on pharmacokinetics and safety of a combined ethinylestradiol/gestodene transdermal contraceptive patch. Drug Des Devel Ther. 2017 Mar 10;11:725-731. doi: 10.2147/DDDT.S131123. eCollection 2017. [PubMed:28331292]
  11. Almstedt HC, Cook MM, Bramble LF, Dabir DV, LaBrie JW: Oral contraceptive use, bone mineral density, and bone turnover markers over 12 months in college-aged females. J Bone Miner Metab. 2020 Jan 25. pii: 10.1007/s00774-019-01081-1. doi: 10.1007/s00774-019-01081-1. [PubMed:31983034]
  12. Regidor PA: Clinical relevance in present day hormonal contraception. Horm Mol Biol Clin Investig. 2018 Oct 26;37(1). pii: /j/hmbci.ahead-of-print/hmbci-2018-0030/hmbci-2018-0030.xml. doi: 10.1515/hmbci-2018-0030. [PubMed:30367791]
  13. Sahu A, Tripathy P, Mohanty J, Nagy A: Doppler analysis of ovarian stromal blood flow changes after treatment with metformin versus ethinyl estradiol-cyproterone acetate in women with polycystic ovarian syndrome: A randomized controlled trial. J Gynecol Obstet Hum Reprod. 2019 May;48(5):335-339. doi: 10.1016/j.jogoh.2018.10.006. Epub 2018 Oct 11. [PubMed:30316907]
  14. FDA Approved Drug Products: Estinyl Ethinylestradiol Oral Tablets (Discontinued) [Link]
  15. FDA Approved Drug Products: Yaz Ethinylestradiol and Drospirenone Oral Tablets [Link]
  16. FDA Approved Drug Products: Taytulla Ethinylestradiol and Norethindrone Acetate Oral Capsules and Ferrous Fumarate Oral Capsules [Link]
  17. FDA Approved Drug Products: Safyral Ethinylestradiol, Drospirenons, and Levomefolate Calcium Oral Tablets and Levomefolate Oral Tablets [Link]
  18. FDA Approved Drugs: Nuvaring® vaginal ring [Link]
  19. FDA Approved Drug Products: Lo Ovral 28 Ethinylestradiol and Norgestrel Oral Tablets and Ferrous Fumarate Oral Tablets [Link]
  20. FDA Approved Drug Products: Femhrt® tablets [Link]
  21. FDA Approved Drug Products: Estrostep Fe Ethinylestradiol and Norethindrone Oral Tablets and Ferrous Fumarate Oral Tablets [Link]
  22. FDA Approved Drug Products: Cyclessa Ethinylestradiol and Desogestrel Oral Tablets [Link]
  23. FDA Approved Drug Products: Annovera Ethinylestradiol and Segesterone Acetate Vaginal System [Link]
  24. FDA Approved Drug Products: Ortho Tri-Cyclen Norgestimate and Ethinyl Estradiol Oral Tablets [Link]
  25. FDA Approved Drug Products: Seasonale Ethinylestradiol and Levonorgestrel Oral Tablets [Link]
Human Metabolome Database
HMDB0001926
KEGG Drug
D00554
KEGG Compound
C07534
PubChem Compound
5991
PubChem Substance
46508618
ChemSpider
5770
BindingDB
50187243
RxNav
4124
ChEBI
4903
ChEMBL
CHEMBL691
ZINC
ZINC000003812897
Therapeutic Targets Database
DAP001018
PharmGKB
PA449527
PDBe Ligand
3WF
RxList
RxList Drug Page
Wikipedia
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
4Active Not RecruitingBasic ScienceOther Disorders of Bone Development and Growth1
4Active Not RecruitingPreventionBacterial Vaginosis (BV)1
4CompletedNot AvailableBirth Control Compliance1
4CompletedNot AvailablePolycystic Ovarian Syndrome / Polycystic Ovaries Syndrome1
4CompletedBasic ScienceAdverse Effect of Oral Contraceptives, Subsequent Encounter1
4CompletedBasic ScienceBone; Disorder, Development and Growth1
4CompletedBasic ScienceContraception2
4CompletedDiagnosticBody Weights / Contraception1
4CompletedDiagnosticBody Weights / Contraceptive Usage1
4CompletedDiagnosticJoint Stabilioty1

Pharmacoeconomics

Manufacturers
  • Schering corp sub schering plough corp
  • Pharmacia and upjohn co
  • Organon usa inc
Packagers
  • Amerisource Health Services Corp.
  • Barr Pharmaceuticals
  • Bayer Healthcare
  • Dept Health Central Pharmacy
  • Duramed
  • Mckesson Corp.
  • NV Organon
  • Organon Pharmaceuticals
  • Ortho Mcneil Janssen Pharmaceutical Inc.
  • Ortho-McNeil-Janssen Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Prasco Labs
  • Schering Corp.
  • Spectrum Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Watson Pharmaceuticals
Dosage Forms
FormRouteStrength
RingVaginal
Tablet, film coatedOral0.02 mg
TabletOral0.03 mg
Tablet, coatedOral2 mg
KitOral
TabletOral0.035 mg
Tablet30 mcg
Tablet, coated0.1 mg
TabletOral150 mcg
Tablet, delayed releaseOral2 mg
TabletOral2 mg
TabletOral
TabletOral10 MICROGRAMMI
TabletOral100 MICROGRAMMI
TabletOral1000 MICROGRAMMI
TabletOral50 MICROGRAMMI
Tablet, coatedOral50 mcg
PatchTransdermal600 mcg
Drug delivery systemVaginal3.474 mg
TabletOral
Tablet, coatedOral20 mcg
Tablet, chewableOral
Tablet, coatedOral30 mcg
Tablet, coatedOral0.15 mg
RingVaginal0.12 MG/24h
Tablet, film coatedOral0.15 mg
Tablet, film coatedOral
Tablet150 mcg
Tablet, coatedOral0.015 mg
TabletOral0.15 mg
Tablet, coatedOral15 mcg
TabletOral0.02 mg
Tablet, coatedOral0.05 mg
Tablet, coatedOral150 mcg
InsertVaginal2.7 mg
Insert, extended releaseVaginal
RingVaginal0.12 mg
RingVaginal11.7 mg
Tablet125 mcg
Patch, extended releaseTransdermal
TabletOral1 mg
Tablet, film coatedOral
Tablet, coatedOral0.075 mg
Tablet, coatedOral3 mg
Tablet, film coatedOral3 mg
Tablet, coatedOral0.02 mg
Tablet, film coatedOral2 mg
Tablet, coatedOral0.03 mg
Tablet, coatedOral150 MICROGRAMMI
Tablet35 mcg
Tablet, coatedOral40 mcg
Capsule, liquid filledOral0.02 mg
PatchTransdermal
TabletOral3 mg
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)Region
US6156742No2000-12-052020-12-05US flag
US6787531No2004-09-072020-08-31US flag
US6933395No2005-08-232017-08-11US flag
US5876746No1999-03-022015-11-20US flag
US5989581No1999-11-232018-04-08US flag
US6214815Yes2001-04-102019-12-09US flag
US6667050No2003-12-232019-04-06US flag
US5898032No1999-04-272017-06-23US flag
USRE39861No2007-09-252017-06-23US flag
US6987101No2006-01-172017-12-22US flag
US7163931No2007-01-162021-12-20US flag
US6958326No2005-10-252021-12-20US flag
US5798338No1998-08-252015-07-10US flag
US7320969No2008-01-222024-01-30US flag
US7615545No2009-11-102023-06-15US flag
US7855190No2010-12-212028-12-05US flag
US7858605No2010-12-282023-06-23US flag
US6500814No2002-12-312018-09-03US flag
US7704984No2010-04-272029-02-02US flag
US6441168No2002-08-272022-07-30US flag
US8617597No2013-12-312030-02-08US flag
US8450299No2013-05-282025-10-07US flag
US8415332No2013-04-092029-03-11US flag
US6652880No2003-11-252020-03-29US flag
US6716814No2004-04-062021-08-16US flag
US9050348No2015-06-092028-07-10US flag
US8221784No2012-07-172021-03-14US flag
US8747888No2014-06-102028-07-10US flag
US8221785No2012-07-172021-03-14US flag
US7384650No2008-06-102021-03-14US flag
US8246978No2012-08-212028-08-26US flag
US8883196No2014-11-112020-11-22US flag
US7045145No2006-05-162021-03-14US flag
US10632066No2019-02-012039-02-01US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

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

Targets

Details
1. Estrogen receptor alpha
Kind
Protein
Organism
Humans
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
Humans
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]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
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]
  2. Ezuruike U, Humphries H, Dickins M, Neuhoff S, Gardner I, Rowland Yeo K: Risk-Benefit Assessment of Ethinylestradiol Using a Physiologically Based Pharmacokinetic Modeling Approach. Clin Pharmacol Ther. 2018 Dec;104(6):1229-1239. doi: 10.1002/cpt.1085. Epub 2018 Apr 27. [PubMed:29637542]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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]
  2. Ezuruike U, Humphries H, Dickins M, Neuhoff S, Gardner I, Rowland Yeo K: Risk-Benefit Assessment of Ethinylestradiol Using a Physiologically Based Pharmacokinetic Modeling Approach. Clin Pharmacol Ther. 2018 Dec;104(6):1229-1239. doi: 10.1002/cpt.1085. Epub 2018 Apr 27. [PubMed:29637542]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Ezuruike U, Humphries H, Dickins M, Neuhoff S, Gardner I, Rowland Yeo K: Risk-Benefit Assessment of Ethinylestradiol Using a Physiologically Based Pharmacokinetic Modeling Approach. Clin Pharmacol Ther. 2018 Dec;104(6):1229-1239. doi: 10.1002/cpt.1085. Epub 2018 Apr 27. [PubMed:29637542]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Ezuruike U, Humphries H, Dickins M, Neuhoff S, Gardner I, Rowland Yeo K: Risk-Benefit Assessment of Ethinylestradiol Using a Physiologically Based Pharmacokinetic Modeling Approach. Clin Pharmacol Ther. 2018 Dec;104(6):1229-1239. doi: 10.1002/cpt.1085. Epub 2018 Apr 27. [PubMed:29637542]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
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
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Stegeman BH, Vos HL, Helmerhorst FM, Rosendaal FR, Reitsma PH, van Hylckama Vlieg A: Genetic variation in the first-pass metabolism of ethinylestradiol, sex hormone binding globulin levels and venous thrombosis risk. Eur J Intern Med. 2017 Jul;42:54-60. doi: 10.1016/j.ejim.2017.05.019. Epub 2017 Jun 1. [PubMed:28579309]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Protein homodimerization activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A4
Uniprot ID
P22310
Uniprot Name
UDP-glucuronosyltransferase 1-4
Molecular Weight
60024.535 Da
References
  1. Ebner T, Remmel RP, Burchell B: Human bilirubin UDP-glucuronosyltransferase catalyzes the glucuronidation of ethinylestradiol. Mol Pharmacol. 1993 Apr;43(4):649-54. [PubMed:8474433]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative reg...
Gene Name
UGT1A3
Uniprot ID
P35503
Uniprot Name
UDP-glucuronosyltransferase 1-3
Molecular Weight
60337.835 Da
References
  1. Stegeman BH, Vos HL, Helmerhorst FM, Rosendaal FR, Reitsma PH, van Hylckama Vlieg A: Genetic variation in the first-pass metabolism of ethinylestradiol, sex hormone binding globulin levels and venous thrombosis risk. Eur J Intern Med. 2017 Jul;42:54-60. doi: 10.1016/j.ejim.2017.05.019. Epub 2017 Jun 1. [PubMed:28579309]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Inducer
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [PubMed:15304429]
  2. Ezuruike U, Humphries H, Dickins M, Neuhoff S, Gardner I, Rowland Yeo K: Risk-Benefit Assessment of Ethinylestradiol Using a Physiologically Based Pharmacokinetic Modeling Approach. Clin Pharmacol Ther. 2018 Dec;104(6):1229-1239. doi: 10.1002/cpt.1085. Epub 2018 Apr 27. [PubMed:29637542]
  3. Rohn-Glowacki KJ, Falany CN: The potent inhibition of human cytosolic sulfotransferase 1A1 by 17alpha-ethinylestradiol is due to interactions with isoleucine 89 on loop 1. Horm Mol Biol Clin Investig. 2014 Dec;20(3):81-90. doi: 10.1515/hmbci-2014-0028. [PubMed:25418972]
  4. Ebner T, Remmel RP, Burchell B: Human bilirubin UDP-glucuronosyltransferase catalyzes the glucuronidation of ethinylestradiol. Mol Pharmacol. 1993 Apr;43(4):649-54. [PubMed:8474433]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Ebner T, Remmel RP, Burchell B: Human bilirubin UDP-glucuronosyltransferase catalyzes the glucuronidation of ethinylestradiol. Mol Pharmacol. 1993 Apr;43(4):649-54. [PubMed:8474433]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Stegeman BH, Vos HL, Helmerhorst FM, Rosendaal FR, Reitsma PH, van Hylckama Vlieg A: Genetic variation in the first-pass metabolism of ethinylestradiol, sex hormone binding globulin levels and venous thrombosis risk. Eur J Intern Med. 2017 Jul;42:54-60. doi: 10.1016/j.ejim.2017.05.019. Epub 2017 Jun 1. [PubMed:28579309]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Specific Function
Amine sulfotransferase activity
Gene Name
SULT1A3
Uniprot ID
P0DMM9
Uniprot Name
Sulfotransferase 1A3
Molecular Weight
34195.96 Da
References
  1. Schrag ML, Cui D, Rushmore TH, Shou M, Ma B, Rodrigues AD: Sulfotransferase 1E1 is a low km isoform mediating the 3-O-sulfation of ethinyl estradiol. Drug Metab Dispos. 2004 Nov;32(11):1299-303. doi: 10.1124/dmd.32.11.. [PubMed:15483196]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sulfotransferase activity
Specific Function
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone. May play a role in the regulation of estrogen r...
Gene Name
SULT1E1
Uniprot ID
P49888
Uniprot Name
Estrogen sulfotransferase
Molecular Weight
35126.185 Da
References
  1. Schrag ML, Cui D, Rushmore TH, Shou M, Ma B, Rodrigues AD: Sulfotransferase 1E1 is a low km isoform mediating the 3-O-sulfation of ethinyl estradiol. Drug Metab Dispos. 2004 Nov;32(11):1299-303. doi: 10.1124/dmd.32.11.. [PubMed:15483196]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
O-methyltransferase activity
Specific Function
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOP...
Gene Name
COMT
Uniprot ID
P21964
Uniprot Name
Catechol O-methyltransferase
Molecular Weight
30036.77 Da
References
  1. Stegeman BH, Vos HL, Helmerhorst FM, Rosendaal FR, Reitsma PH, van Hylckama Vlieg A: Genetic variation in the first-pass metabolism of ethinylestradiol, sex hormone binding globulin levels and venous thrombosis risk. Eur J Intern Med. 2017 Jul;42:54-60. doi: 10.1016/j.ejim.2017.05.019. Epub 2017 Jun 1. [PubMed:28579309]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Pedersen RS, Noehr-Jensen L, Brosen K: Inhibitory effect of oral contraceptives on CYP2C19 activity is not significant in carriers of the CYP2C19*17 allele. Clin Exp Pharmacol Physiol. 2013 Oct;40(10):683-8. doi: 10.1111/1440-1681.12153. [PubMed:23844835]
  2. Palovaara S, Tybring G, Laine K: The effect of ethinyloestradiol and levonorgestrel on the CYP2C19-mediated metabolism of omeprazole in healthy female subjects. Br J Clin Pharmacol. 2003 Aug;56(2):232-7. doi: 10.1046/j.1365-2125.2003.01868.x. [PubMed:12895199]
  3. Chang SY, Chen C, Yang Z, Rodrigues AD: Further assessment of 17alpha-ethinyl estradiol as an inhibitor of different human cytochrome P450 forms in vitro. Drug Metab Dispos. 2009 Aug;37(8):1667-75. doi: 10.1124/dmd.109.026997. Epub 2009 May 19. [PubMed:19454483]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Kuhnz W, Pfeffer M, al-Yacoub G: Protein binding of the contraceptive steroids gestodene, 3-keto-desogestrel and ethinylestradiol in human serum. J Steroid Biochem. 1990 Feb;35(2):313-8. doi: 10.1016/0022-4731(90)90290-9. [PubMed:2308344]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
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]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Estradiol trans-inhibits BSEP only after its secretion into bile canaliculi by Mrp2.
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]
  3. Stieger B, Fattinger K, Madon J, Kullak-Ublick GA, Meier PJ: Drug- and estrogen-induced cholestasis through inhibition of the hepatocellular bile salt export pump (Bsep) of rat liver. Gastroenterology. 2000 Feb;118(2):422-30. [PubMed:10648470]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
Curator comments
This transporter is induced at low concentrations of ethinylestradiol and inhibited at higher concentrations.
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
Humans
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]
  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
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 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]

Drug created on June 13, 2005 07:24 / Updated on October 25, 2020 09:16

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