Compound Detail
CHEMBL691
ETHINYL ESTRADIOL 💊 Approved Drug
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💊 Approved Drug
Basic Information
| ChEMBL ID | CHEMBL691 |
| Name | ETHINYL ESTRADIOL |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | BFPYWIDHMRZLRN-SLHNCBLASA-N |
| Therapeutic | ✓ Yes |
29
Targets
67
Activities
4
Assay Types
13
PK Parameters
20
Publications
30
Known Names
20
Indications
1
Mechanisms
Molecular Properties
296.4
MW (Da)
3.61
ALogP
2
HBA
2
HBD
40.5
PSA (Ų)
0.72
QED
0
Ro5 Violations
0
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1982 |
| Availability | Prescription |
| Chirality | Single Enantiomer |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| Estrogen receptor alpha agonist | AGONIST | Estrogen receptor | ✓ | ✓ |
Indications
Acne Vulgaris Neoplasms Neoplasms Amenorrhea Anorexia Nervosa Bone Diseases, Metabolic Breast Neoplasms Dysmenorrhea Endometriosis Migraine Disorders Neural Tube Defects Polycystic Ovary Syndrome Pregnancy Turner Syndrome Bulimia Bulimia Nervosa Depressive Disorder Endometrial Neoplasms Hidradenitis Suppurativa Hyperandrogenism
ATC Classification
G03CA01
ethinylestradiol
Level 1: GENITO URINARY SYSTEM AND SEX HORMONES
Level 2: SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
L02AA03
ethinylestradiol
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ENDOCRINE THERAPY
Activity Summary
IC50 34 meas. best 9.62
Ki 26 meas. best 9.89
EC50 4 meas. best 9.8
Kd 3 meas. best 8.37
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| Estrogen receptor CHEMBL206 | Ki | 9.89 | 9.89 | 0.1 | 1 |
| Estrogen receptor beta CHEMBL242 | EC50 | 9.8 | 9.615 | 0.2 | 2 |
| Unchecked CHEMBL612545 | IC50 | 9.62 | 6.06 | 0.2 | 4 |
| Estrogen receptor CHEMBL206 | EC50 | 9.52 | 9.52 | 0.3 | 1 |
| Estrogen receptor CHEMBL206 | IC50 | 9.35 | 8.7167 | 0.4 | 3 |
| Sulfotransferase 1A1 CHEMBL1743291 | Kd | 8.37 | 7.335 | 4.3 | 2 |
| Aldehyde oxidase CHEMBL3257 | IC50 | 8.3 | 7.27 | 5.0 | 2 |
| Estrogen receptor beta CHEMBL242 | IC50 | 8.09 | 7.92 | 8.1 | 2 |
| Sulfotransferase 1A1 CHEMBL1743291 | Ki | 8.05 | 7.8667 | 8.9 | 3 |
| Sulfotransferase 1A1 CHEMBL1743291 | IC50 | 7.7 | 7.7 | 20.0 | 1 |
| Sodium-dependent serotonin transporter CHEMBL228 | Ki | 7.54 | 7.54 | 29.0 | 1 |
| Sodium-dependent serotonin transporter CHEMBL228 | IC50 | 7.27 | 7.27 | 54.0 | 1 |
| Progesterone receptor CHEMBL1909044 | Ki | 6.86 | 6.86 | 139.0 | 1 |
| Sex hormone-binding globulin CHEMBL3305 | Kd | 6.81 | 6.81 | 154.9 | 1 |
| Aldehyde oxidase CHEMBL3257 | Ki | 6.37 | 5.905 | 430.0 | 2 |
| Sodium-dependent dopamine transporter CHEMBL238 | Ki | 6.35 | 6.35 | 444.0 | 1 |
| Sodium-dependent dopamine transporter CHEMBL238 | IC50 | 6.25 | 6.25 | 559.0 | 1 |
| Glucocorticoid receptor CHEMBL2034 | Ki | 6.11 | 6.11 | 777.0 | 1 |
| Cytochrome P450 2B6 CHEMBL4729 | Ki | 6.1 | 6.075 | 800.0 | 2 |
| Sodium-dependent noradrenaline transporter CHEMBL222 | Ki | 6.02 | 6.02 | 951.0 | 1 |
| Sodium-dependent noradrenaline transporter CHEMBL222 | IC50 | 6.02 | 6.02 | 959.0 | 1 |
| Progesterone receptor CHEMBL1909044 | IC50 | 5.97 | 5.97 | 1067.0 | 1 |
| Androgen receptor CHEMBL3072 | Ki | 5.96 | 5.96 | 1090.0 | 1 |
| 5-hydroxytryptamine receptor 4 CHEMBL5017 | Ki | 5.88 | 5.88 | 1326.0 | 1 |
| Androgen receptor CHEMBL3072 | IC50 | 5.79 | 5.44 | 1634.0 | 2 |
| Glucocorticoid receptor CHEMBL2034 | IC50 | 5.77 | 5.77 | 1710.0 | 1 |
| Solute carrier family 22 member 2 CHEMBL1743122 | IC50 | 5.66 | 5.66 | 2200.0 | 1 |
| HEK293 CHEMBL614818 | EC50 | 5.52 | 5.52 | 3000.0 | 1 |
| Nuclear receptor subfamily 1 group I member 3 CHEMBL5503 | IC50 | 5.52 | 5.52 | 3000.0 | 1 |
| Polyunsaturated fatty acid lipoxygenase ALOX15 CHEMBL4358 | IC50 | 5.25 | 5.25 | 5678.0 | 1 |
| Unchecked CHEMBL612545 | Ki | 5.17 | 4.7875 | 6793.0 | 4 |
| 5-hydroxytryptamine receptor 4 CHEMBL5017 | IC50 | 5.1 | 5.1 | 7953.0 | 1 |
| Kappa-type opioid receptor CHEMBL237 | Ki | 4.99 | 4.99 | 10358.0 | 1 |
| Mu-type opioid receptor CHEMBL233 | Ki | 4.96 | 4.96 | 10867.0 | 1 |
| Cytochrome P450 2B1 CHEMBL3335 | Ki | 4.96 | 4.96 | 11000.0 | 1 |
| Adenosine receptor A2a CHEMBL251 | Ki | 4.93 | 4.93 | 11751.0 | 1 |
| Bile salt export pump CHEMBL6020 | IC50 | 4.85 | 4.85 | 14000.0 | 1 |
| Cytochrome P450 3A4 CHEMBL340 | Ki | 4.75 | 4.75 | 18000.0 | 1 |
| Adenosine receptor A3 CHEMBL256 | Ki | 4.73 | 4.73 | 18610.0 | 1 |
| Multidrug and toxin extrusion protein 2 CHEMBL1743127 | IC50 | 4.7 | 4.7 | 20200.0 | 1 |
| Adenosine receptor A2a CHEMBL251 | IC50 | 4.68 | 4.68 | 20931.0 | 1 |
| Multidrug and toxin extrusion protein 1 CHEMBL1743126 | IC50 | 4.68 | 4.68 | 21100.0 | 1 |
| UDP-glucuronosyltransferase 1A1 CHEMBL1287617 | IC50 | 4.68 | 4.52 | 21000.0 | 2 |
| Kappa-type opioid receptor CHEMBL237 | IC50 | 4.59 | 4.59 | 25894.0 | 1 |
| Mu-type opioid receptor CHEMBL233 | IC50 | 4.57 | 4.57 | 26769.0 | 1 |
| MDA-MB-231 CHEMBL400 | IC50 | 4.48 | 4.48 | 32900.0 | 1 |
| Adenosine receptor A3 CHEMBL256 | IC50 | 4.48 | 4.48 | 32925.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| CL | 64.0 | mL.min-1.kg-1 | Rattus norvegicus |
| CL | 5.0 | mL.min-1.kg-1 | Homo sapiens |
| CL | 7.0 | mL.min-1.kg-1 | Homo sapiens |
| CL | 17.0 | mL.min-1.kg-1 | Macaca |
| CL | 25.0 | mL.min-1.kg-1 | Canis lupus familiaris |
| CL | 0.00034 | mL.min-1.g-1 | Homo sapiens |
| CL | 8.7e-05 | mL.min-1.g-1 | Homo sapiens |
| CL | 0.427 | uL/min | Homo sapiens |
| F | 49.0 | % | Homo sapiens |
| F | 40.0 | % | Homo sapiens |
| Fu | 0.014 | - | Homo sapiens |
| MRT | 11.0 | hr | Homo sapiens |
| T1/2 | 9.7 | hr | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
Literature References
Data from ChEMBL 36 via Core Engine