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Ethinyl Estradiol

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Also known as 17alpha-ethinylestradiolEstinylEthinyl estradiol component of alesseEthinyl estradiol component of altaveraEthinyl estradiol component of annoveraEthinyl estradiol component of aranelleEthinyl estradiol component of avianeEthinyl estradiol component of balcoltraEthinyl estradiol component of bekyreeEthinyl estradiol component of beyazEthinyl estradiol component of breviconEthinyl estradiol component of cryselleEthinyl estradiol component of cyclessaEthinyl estradiol component of desogenEthinyl estradiol component of elifemmeEthinyl estradiol component of enpresseEthinyl estradiol component of enskyceEthinyl estradiol component of femcon feEthinyl estradiol component of femhrt

Summary

Ethinyl Estradiol (CHEMBL691) is an approved small-molecule xenoestrogen (ATC L02AA03) targeting SLC36A1, ESR1, and ESR2; indicated across 34 conditions including neoplasm and acne.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: L02AA03 (+1 more)
  • Targets: 3 (SLC36A1, ESR1, ESR2)
  • Indications: 34 conditions
  • Clinical trials: 118
  • Chemistry: 296.4 Da · C20H24O2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL691
NameEthinyl Estradiol
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID5991
ChEBICHEBI:4903
ATCL02AA03, G03CA01
Molecular formulaC20H24O2
Molecular weight296.4
InChIKeyBFPYWIDHMRZLRN-SLHNCBLASA-N

SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(C#C)O)CCC4=C3C=CC(=C4)O

IUPAC name: (8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol

ChEBI definition: A 3-hydroxy steroid that is estradiol substituted by a ethynyl group at position 17. It is a xenoestrogen synthesized from estradiol and has been shown to exhibit high estrogenic potency on oral administration.

Pharmacological roles (ChEBI): xenoestrogen.

Also known as: 17alpha-ethinylestradiol, Estinyl, Ethinyl estradiol, Ethinyl estradiol component of alesse, Ethinyl estradiol component of altavera, Ethinyl estradiol component of annovera, Ethinyl estradiol component of aranelle, Ethinyl estradiol component of aviane, Ethinyl estradiol component of balcoltra, Ethinyl estradiol component of bekyree, Ethinyl estradiol component of beyaz, Ethinyl estradiol component of brevicon

Patent coverage: 11,583 distinct patent families (40,543 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 40,305 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
SLC36A1Proton-coupled Amino acid Transporter 1Inhibition4.60.2%Q7Z2H8
ESR1Estrogen receptor-αAgonist8.71.7%P03372
ESR2Estrogen receptor-βAgonist8.090.2%Q92731

Broader ChEMBL bioactivity targets: 36 (assay-derived). Sample: UDP-glucuronosyltransferase 1A1, Solute carrier family 22 member 2, Multidrug and toxin extrusion protein 1, Multidrug and toxin extrusion protein 2, Sulfotransferase 1A1, 5-hydroxytryptamine receptor 2B, Androgen receptor, Glucocorticoid receptor, Estrogen receptor, Thromboxane A2 receptor.

Bioactivity

ChEMBL activities: 53 potent at pChembl ≥ 5 of 78 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
ESR19.89Ki0.13nMCHEMBL_ACT_7675803
ESR29.8EC500.16nMCHEMBL_ACT_22894631
ESR19.52EC500.3nMCHEMBL_ACT_22894598
ESR29.43EC500.37nMCHEMBL_ACT_22894584
ESR19.35IC500.45nMCHEMBL_ACT_7675802
ESR18.7IC502nMCHEMBL_ACT_1717846
ESR18.52AC503nMCHEMBL_ACT_25138775
SULT1A18.37Kd4.3nMCHEMBL_ACT_15463336
AOX18.3IC505nMCHEMBL_ACT_25002912
ESR18.1IC508.04nMCHEMBL_ACT_3285749
ESR28.09IC508.1nMCHEMBL_ACT_1717860
SULT1A18.05Ki8.9nMCHEMBL_ACT_15463334
ESR17.96AC5011nMCHEMBL_ACT_25167102
SULT1A17.83Ki14.9nMCHEMBL_ACT_15463335
ESR27.75IC5017.78nMCHEMBL_ACT_3285759
SULT1A17.72Ki19nMCHEMBL_ACT_15463333
SULT1A17.7IC5020nMCHEMBL_ACT_15463332
PGR7.7AC5020nMCHEMBL_ACT_25204208
SLC6A47.54Ki29nMCHEMBL_ACT_7677934
SLC6A47.27IC5054nMCHEMBL_ACT_7677933
AR7.05AC5090nMCHEMBL_ACT_25203275
NR3C16.92AC50120nMCHEMBL_ACT_25175624
SHBG6.81Kd154.9nMCHEMBL_ACT_2155693
SLC6A46.51AC50310nMCHEMBL_ACT_25151244
AOX16.37Ki430nMCHEMBL_ACT_15459133
SLC6A36.35Ki444nMCHEMBL_ACT_7675799
SULT1A16.3Kd500nMCHEMBL_ACT_15463338
SLC6A36.25IC50559nMCHEMBL_ACT_7675798
AOX16.24IC50570nMCHEMBL_ACT_5102812
SLC6A46.11AC50780nMCHEMBL_ACT_25150087

Target pathways

Aggregated over 3 target gene(s): SLC36A1, ESR1, ESR2.

Top Reactome pathways

22 total, by targets touching each:

PathwayTargetsGenes
PIP3 activates AKT signaling2ESR1, ESR2
Constitutive Signaling by Aberrant PI3K in Cancer2ESR1, ESR2
Nuclear Receptor transcription pathway2ESR1, ESR2
PI5P, PP2A and IER3 Regulate PI3K/AKT Signaling2ESR1, ESR2
ESR-mediated signaling2ESR1, ESR2
Extra-nuclear estrogen signaling2ESR1, ESR2
Nuclear signaling by ERBB41ESR1
Amino acid transport across the plasma membrane1SLC36A1
Transport of small molecules1SLC36A1
SUMOylation of intracellular receptors1ESR1
R-HSA-4253931SLC36A1
SLC-mediated transmembrane transport1SLC36A1
Proton-coupled neutral amino acid transporters1SLC36A1
Ovarian tumor domain proteases1ESR1
TFAP2 (AP-2) family regulates transcription of growth factors and their receptors1ESR1
RUNX1 regulates estrogen receptor mediated transcription1ESR1
RUNX1 regulates transcription of genes involved in WNT signaling1ESR1
Regulation of RUNX2 expression and activity1ESR1
Estrogen-dependent gene expression1ESR1
Mitochondrial unfolded protein response (UPRmt)1ESR1
Developmental Lineage of Mammary Gland Luminal Epithelial Cells1ESR1
Developmental Lineage of Mammary Gland Alveolar Cells1ESR1

Dominant GO biological processes

GO termTargets
negative regulation of transcription by RNA polymerase II2
regulation of DNA-templated transcription2
regulation of transcription by RNA polymerase II2
signal transduction2
estrogen receptor signaling pathway2
positive regulation of DNA-templated transcription2
positive regulation of transcription by RNA polymerase II2
obsolete positive regulation of DNA-binding transcription factor activity2
cellular response to estradiol stimulus2
cellular response to oxygen-containing compound2
monoatomic ion transport1
amino acid transport1
taurine transmembrane transport1
L-alanine transport1
glycine transport1

Indications & clinical

Indications

34 indications (3 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
neoplasm4MONDO:0005070EFO:0000616
acne4MONDO:0011438EFO:0003894
polycystic ovary syndrome3MONDO:0008487EFO:0000660
amenorrhea3MONDO:0001836EFO:0010269
breast neoplasm3MONDO:0021100MONDO:0007254
migraine disorder3MONDO:0005277MONDO:0005277
neural tube defect3MONDO:0018075MONDO:0018075
Turner syndrome3MONDO:0019499MONDO:0019499
anorexia nervosa3MONDO:0005351MONDO:0005351
endometriosis3MONDO:0005133EFO:0001065
osteoporosis2MONDO:0005298EFO:0003882
hidradenitis suppurativa2MONDO:0006559EFO:1000710
bulimia nervosa2MONDO:0005452EFO:0005204
binge eating disorder2MONDO:0005582EFO:0005924
endometrium neoplasm2MONDO:0021251MONDO:0011962
depressive disorder2MONDO:0002050MONDO:0002050
premenstrual tension2MONDO:0004169MONDO:0004169
B-cell chronic lymphocytic leukemia1MONDO:0004948EFO:0000095
HIV infectious disease1MONDO:0005109EFO:0000764
hepatitis C virus infection1MONDO:0005231EFO:0003047
chronic hepatitis C virus infection1MONDO:0005354EFO:0004220
female infertility1MONDO:0021124EFO:0008560
chronic hepatitis B virus infection1MONDO:0005366EFO:0004239
metabolic dysfunction-associated steatohepatitis1MONDO:0007027EFO:1001249
type 2 diabetes mellitus1MONDO:0005148MONDO:0005148
cystic fibrosis1MONDO:0009061MONDO:0009061
obesity disorder1MONDO:0011122EFO:0001073

7 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 118.

Phase distribution

PhaseTrials
PHASE142
PHASE424
PHASE323
Not specified15
PHASE214

Top trials by phase / activity

NCTPhaseStatusTitle
NCT05058872PHASE4RECRUITINGContraceptive Hormone and Reward Measurement (CHARM Study)
NCT00204451PHASE4COMPLETEDHuman Ovarian Follicular Dynamics and Emergency Contraception
NCT00261482PHASE4COMPLETEDEvaluation of Women’s Experience With EVRA (Norelgestromin + Ethinyl Estradiol) Transdermal Contraceptive Patch Compared With Previous Methods of Contraception.
NCT00269620PHASE4COMPLETEDPARIS or PAtch RIng Study: A Trial to Evaluate NuvaRing Versus OrthoEvra
NCT00640224PHASE4COMPLETEDInsulin Resistance, Polycystic Ovary Syndrome, and Bone Research Study
NCT00662454PHASE4COMPLETEDOral Contraceptive Efficacy and Body Weight
NCT00732693PHASE4COMPLETEDEvaluation of Physiologic and Standard Sex Steroid Replacement Regimens in Women With Premature Ovarian Failure
NCT00745901PHASE4COMPLETEDStudy to Evaluate Cycle Control With Norgestimate/Ethinyl Estradiol and Drospirenone/Ethinyl Estradiol in Healthy Sexually Active Females
NCT00829114PHASE4COMPLETEDInteractions Between Antiretrovirals (ARVs) and Combined Oral Contraceptives (COCs)
NCT01056042PHASE4COMPLETEDEfficacy of Injectable Contraceptive and Oral Contraceptive Administered After Surgical Treatment of Endometriosis With Pain
NCT01103518PHASE4UNKNOWNEthinyl Estradiol and Cyproterone Acetate in Irregular Menstruation
NCT01174524PHASE4COMPLETEDImprovement of Quality of Life in Patients Using Low-dose Pills in the Different Phases of Menacme
NCT01466673PHASE4COMPLETEDAn Efficacy and Safety Study Comparing Oral Contraceptive Containing Norgestimate or Desogestrel for Acne Treatment
NCT01490190PHASE4COMPLETEDStudy of the Use of a Contraceptive Vaginal Ring (NuvaRing) in Normal Daily Practice in Indian Women (P07733)
NCT01501448PHASE4COMPLETEDOral Estradiol Valerate Versus Oral Contraceptive Pill in Invitro Fertilization Patients
NCT02210702PHASE4UNKNOWNOral Contraceptive Ethinyl Estradiol Dose Effect on Postpartum Depression and Sexual Functioning Scales
NCT02352090PHASE4COMPLETEDSynthetic vs Natural Estrogen in Combined Oral Contraception
NCT02531321PHASE4TERMINATEDProtease Inhibitors and Combined Oral Contraceptive Pharmacokinetics and Pharmacodynamics
NCT02866786PHASE4COMPLETEDThe Effects of OCP and Metformin on Clinical, Hormonal, Metabolic and Ultrasonographic Characteristics in PCOS
NCT03124524PHASE4COMPLETEDTreatment Choice in Primary Dysmenorrhea
NCT04828824PHASE4COMPLETEDPremature Discontinuation of Contraceptive Implants
NCT05002738PHASE4COMPLETEDDesogestrel-containing COCP Pharmacokinetic Validation Study
NCT06316206PHASE4COMPLETEDThe Use of Ethinylestradiol/Dienogest in Random Start Rapid Endometrial Preparation
NCT06324851PHASE4COMPLETEDThe Use of Drospirenone/Estetrol, Nomegestrol Acetate/Estradiol and Ethinylestradiol/Dienogest in Random Start Rapid Endometrial Preparation
NCT00128934PHASE3COMPLETEDStudy Evaluating Combination of Levonorgestrel (LNG) and Ethinyl Estradiol (EE) in Premenstrual Dysphoric Disorder
NCT00161681PHASE3COMPLETEDStudy Evaluating Levonorgestrel/Ethinyl Estradiol (LNG/EE) in PMS
NCT00191113PHASE3COMPLETEDSomatropin Treatment to Final Height in Turner Syndrome
NCT00195559PHASE3COMPLETEDStudy Evaluating Combination of Levonorgestrel and Ethinyl Estradiol in Pre-Menstrual Dysphoric Disorder
NCT00212277PHASE3COMPLETEDEfficacy and Safety,Long-term Study of Low-dose Oral Contraceptive Pill to Treat Dysmenorrhea.
NCT00212342PHASE3COMPLETEDEfficacy and Safety Study of Low Dose Oral Contraceptive Pill to Treat Dysmenorrhea
NCT00236769PHASE3COMPLETEDA Study of Efficacy and Safety With the Transdermal Contraceptive System.
NCT00391807PHASE3COMPLETEDStudy of Safety and Efficacy of an Oral Contraceptive
NCT00468481PHASE3COMPLETEDEfficacy and Safety Study for an Oral Contraceptive Containing Folate
NCT00477633PHASE3COMPLETEDStudy of Safety and Efficacy of an Oral Contraceptive
NCT00511355PHASE3COMPLETEDEffects on Hemostasis, Lipids, Carbohydrate Metabolism, Adrenal & Thyroid Function of the Combined Oral Contraceptive NOMAC-E2 Compared to a COC Containing LNG-EE (292004)(COMPLETED)(P05764)
NCT00722761PHASE3COMPLETEDSafety and Efficacy Of Drospirenone and Ethinyl Estradiol vs Placebo in the Treatment of Truncal Acne
NCT00909857PHASE3COMPLETEDEffect on Primary Dysmenorrhea
NCT00914693PHASE3COMPLETEDEU/LA Pearl Index Study - Transdermal Contraceptive Patch
NCT00932321PHASE3COMPLETEDStudy of Safety and Efficacy of an Oral Contraceptive
NCT00946192PHASE3COMPLETEDFat Mediated Modulation of Reproductive and Endocrine Function in Young Athletes

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

188 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
FULVESTRANTChEMBL + PubChemPhase 4 (approved)ESR1, ESR2
BAZEDOXIFENEChEMBLPhase 4 (approved)ESR1, ESR2
BITHIONOLChEMBLPhase 4 (approved)ESR1, ESR2
CISPLATINChEMBLPhase 4 (approved)ESR1, ESR2
DIETHYLSTILBESTROLChEMBLPhase 4 (approved)ESR1, ESR2
ELACESTRANTChEMBLPhase 4 (approved)ESR1, ESR2
ESTETROLChEMBLPhase 4 (approved)ESR1, ESR2
ESTRADIOLChEMBLPhase 4 (approved)ESR1, ESR2
ESTRIOLChEMBLPhase 4 (approved)ESR1, ESR2
ESTRONEChEMBLPhase 4 (approved)ESR1, ESR2
HEXACHLOROPHENEChEMBLPhase 4 (approved)ESR1, ESR2
LASOFOXIFENEChEMBLPhase 4 (approved)ESR1, ESR2
MEDROXYPROGESTERONEChEMBLPhase 4 (approved)ESR1, ESR2
MIFEPRISTONEChEMBLPhase 4 (approved)ESR1, ESR2
PHENOLPHTHALEINChEMBLPhase 4 (approved)ESR1, ESR2
RALOXIFENEChEMBLPhase 4 (approved)ESR1, ESR2
SPIRONOLACTONEChEMBLPhase 4 (approved)ESR1, ESR2
TAMOXIFENChEMBLPhase 4 (approved)ESR1, ESR2
ACOLBIFENEChEMBLPhase 3ESR1, ESR2
AFIMOXIFENEChEMBLPhase 3ESR1, ESR2
AMCENESTRANTChEMBLPhase 3ESR1, ESR2
ARZOXIFENEChEMBLPhase 3ESR1, ESR2
BENSERAZIDEChEMBLPhase 3ESR1, ESR2
ALFATRADIOLChEMBLPhase 2ESR1, ESR2
AUS-131ChEMBLPhase 2ESR1, ESR2
BRILANESTRANTChEMBLPhase 2ESR1, ESR2
DAIDZEINChEMBLPhase 2ESR1, ESR2
ERTEBERELChEMBLPhase 2ESR1, ESR2
GENISTEINChEMBLPhase 2ESR1, ESR2
GTX-758ChEMBLPhase 2ESR1, ESR2
IDOXIFENEChEMBLPhase 2ESR1, ESR2
LEVORMELOXIFENEChEMBLPhase 2ESR1, ESR2
MOXESTROLChEMBLPhase 2ESR1, ESR2
PIPENDOXIFENEChEMBLPhase 2ESR1, ESR2
PRINABERELChEMBLPhase 2ESR1, ESR2
STALLIMYCINChEMBLPhase 2ESR1, ESR2
BosentanPubChemApprovedESR1, ESR2
DihydroergotaminePubChemApprovedESR1, ESR2
FidaxomicinPubChemApprovedESR1, ESR2
PropoxyphenePubChemApprovedESR1, ESR2
PyrazinamidePubChemApprovedESR1, ESR2
ACETOPHENAZINEChEMBLPhase 4 (approved)ESR1
ALECTINIBChEMBLPhase 4 (approved)ESR1
APOMORPHINEChEMBLPhase 4 (approved)ESR1
ARIPIPRAZOLEChEMBLPhase 4 (approved)ESR1
ASPIRINChEMBLPhase 4 (approved)ESR1
AZTREONAMChEMBLPhase 4 (approved)ESR1
BELINOSTATChEMBLPhase 4 (approved)ESR1
BENZBROMARONEChEMBLPhase 4 (approved)ESR1
BEXAROTENEChEMBLPhase 4 (approved)ESR1
BISACODYLChEMBLPhase 4 (approved)ESR1
BROMOCRIPTINEChEMBLPhase 4 (approved)ESR1
BUTOCONAZOLEChEMBLPhase 4 (approved)ESR1
CANDESARTAN CILEXETILChEMBLPhase 4 (approved)ESR1
CASPOFUNGINChEMBLPhase 4 (approved)ESR1
CEFADROXILChEMBLPhase 4 (approved)ESR1
CEFEPIMEChEMBLPhase 4 (approved)ESR1
CEFTAZIDIMEChEMBLPhase 4 (approved)ESR1
CERIVASTATINChEMBLPhase 4 (approved)ESR1
CHLOROTRIANISENEChEMBLPhase 4 (approved)ESR1

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot