Ethinyl estradiol
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1982
- First approval year
- 1982
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Ethinyl estradiol
- Molecular weight
- 296.41
- Structure (SMILES)
- C#C[C@]1(O)CC[C@H]2[C@@H]3CCc4cc(O)ccc4[C@H]3CC[C@@]21C
- estinyl
- Estinyl
- ethinyl estradiol component of alesse
- Ethinyl estradiol component of alesse
- ethinyl estradiol component of altavera
- Ethinyl estradiol component of altavera
- ethinyl estradiol component of annovera
- Ethinyl estradiol component of annovera
- ethinyl estradiol component of aranelle
- Ethinyl estradiol component of aranelle
- ethinyl estradiol component of aviane
- Ethinyl estradiol component of aviane
- ethinyl estradiol component of balcoltra
- Ethinyl estradiol component of balcoltra
- ethinyl estradiol component of bekyree
- Ethinyl estradiol component of bekyree
- ethinyl estradiol component of beyaz
- Ethinyl estradiol component of beyaz
- ethinyl estradiol component of brevicon
- Ethinyl estradiol component of brevicon
- ethinyl estradiol component of cryselle
- Ethinyl estradiol component of cryselle
- ethinyl estradiol component of cyclessa
- Ethinyl estradiol component of cyclessa
- ethinyl estradiol component of desogen
And 129 more, listed on the interactive page.
- 0 075mg gestodene 0 03mg ethinylestradiol
- 17 ethinylestradiol
- 17-ethinylestradiol
- 17alpha ethinylestradiol
- 17alpha-ethinylestradiol
- 19 nor 17α pregna 1 3 5 10 trien 20 yne 3 17 diol
- 19 norpregna 1 3 5 10 trien 20 yne 3 17 diol 17 alpha
- 19-Nor-17α-pregna-1,3,5(10)-trien-20-yne-3,17-diol
- 19-NORPREGNA-1,3,5(10)-TRIEN-20-YNE-3,17-DIOL, (17.ALPHA.)-
- alesse component ethinyl estradiol
- ALESSE COMPONENT ETHINYL ESTRADIOL
- altavera component ethinyl estradiol
- ALTAVERA COMPONENT ETHINYL ESTRADIOL
- annovera component ethinyl estradiol
- ANNOVERA COMPONENT ETHINYL ESTRADIOL
- aranelle component ethinyl estradiol
- ARANELLE COMPONENT ETHINYL ESTRADIOL
- aviane component ethinyl estradiol
- AVIANE COMPONENT ETHINYL ESTRADIOL
- bekyree component ethinyl estradiol
- BEKYREE COMPONENT ETHINYL ESTRADIOL
- beyaz component ethinyl estradiol
- BEYAZ COMPONENT ETHINYL ESTRADIOL
- brevicon component ethinyl estradiol
- BREVICON COMPONENT ETHINYL ESTRADIOL
And 186 more, listed on the interactive page.
- CAS registry numbers
- 57-63-6
- ChEMBL ID
- CHEMBL691
- InChIKey
- BFPYWIDHMRZLRN-SLHNCBLASA-N
- PubChem compound IDs
- 5991
- RxNorm IDs (RxCUI)
- 4124
- FDA ingredient codes (UNII)
- 423D2T571U
- G03CA01
- L02AA03
Sources for recorded values
- Applicant
- ORGANON USA ORGANON
- Approval date
- 3 Oct 2001
- Application number
- NDA021187
- First in class
- No
- Orphan designation
- No
- Availability
- Prescription only
- Pharmacology name
- ethinylestradiol
- Type
- Metabolite
- Drug name stem
- estr-
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Oral
- topical
- Action type
- Agonist
- Target
- Estrogen receptor-β
- Gene symbol
- Estrogen receptor-β
- Action
- Agonist
- Action type
- Agonist
- Target
- Estrogen receptor-α
- Gene symbol
- ESR1
- Protein identifier
- P03372
- Median affinity
- 8.7
- Affinity units
- pIC50
- Primary target
- Yes
- Action
- Agonist
- Action type
- Agonist
- Target
- Estrogen receptor-β
- Gene symbol
- ESR2
- Protein identifier
- Q92731
- Median affinity
- 8.09
- Affinity units
- pIC50
- Mechanism
- Estrogen receptor alpha agonist
- Action type
- Agonist
- Target
- Estrogen receptor
- Protein identifier
- P03372
- Action type
- Inhibitor
- Target
- Proton-coupled Amino acid Transporter 1
- Gene symbol
- Proton-coupled Amino acid Transporter 1
- Action
- Inhibition
- Action type
- Inhibitor
- Target
- Proton-coupled Amino acid Transporter 1
- Gene symbol
- SLC36A1
- Protein identifier
- Q7Z2H8
- Affinity units
- pIC50
Open Targets mechanisms
- Mechanism
- Estrogen receptor alpha agonist
- Action type
- Agonist
- Target
- Estrogen receptor
DrugCentral mechanisms
- Action type
- Agonist
- Gene symbol
- ESR1
- Protein identifier
- P03372
- Organism
- Homo sapiens
- Target development level
- Clinical
- Condition
- Leukemia, Lymphocytic, Chronic, B-Cell
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000095
- Subject identifier
- D015451
- Condition
- HIV Infections
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000180
- Subject identifier
- D015658
- Condition
- Neoplasms
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000616
- Subject identifier
- D009369
- Condition
- Polycystic Ovary Syndrome
- Highest recorded phase
- 3
- Condition identifier
- EFO:0000660
- Subject identifier
- D011085
- Condition
- HIV Infections
- Highest recorded phase
- 1
- Condition identifier
- EFO:0000764
- Subject identifier
- D015658
- Condition
- Endometriosis
- Highest recorded phase
- 3
- Condition identifier
- EFO:0001065
- Subject identifier
- D004715
- Condition
- Obesity
- Highest recorded phase
- 1
- Condition identifier
- EFO:0001073
- Subject identifier
- D009765
- Condition
- Pregnancy
- Highest recorded phase
- 3
- Condition identifier
- EFO:0002950
- Subject identifier
- D011247
- Condition
- Hepatitis C
- Highest recorded phase
- 1
- Condition identifier
- EFO:0003047
- Subject identifier
- D006526
- Condition
- Osteoporosis
- Highest recorded phase
- 2
- Condition identifier
- EFO:0003882
- Subject identifier
- D010024
- Condition
- Acne Vulgaris
- Highest recorded phase
- 4
- Condition identifier
- EFO:0003894
- Subject identifier
- D000152
- Condition
- Hepatitis C, Chronic
- Highest recorded phase
- 1
- Condition identifier
- EFO:0004220
- Subject identifier
- D019698
- Condition
- Hepatitis B, Chronic
- Highest recorded phase
- 1
- Condition identifier
- EFO:0004239
- Subject identifier
- D019694
- Condition
- Bulimia Nervosa
- Highest recorded phase
- 2
- Condition identifier
- EFO:0005204
- Subject identifier
- D052018
- Condition
- Bulimia
- Highest recorded phase
- 2
- Condition identifier
- EFO:0005924
- Subject identifier
- D002032
- Condition
- Infertility, Female
- Highest recorded phase
- 1
- Condition identifier
- EFO:0008560
- Subject identifier
- D007247
- Condition
- Hyperandrogenism
- Highest recorded phase
- 2
- Condition identifier
- EFO:0009006
- Subject identifier
- D017588
- Condition
- Amenorrhea
- Highest recorded phase
- 3
- Condition identifier
- EFO:0010269
- Subject identifier
- D000568
- Condition
- Hidradenitis Suppurativa
- Highest recorded phase
- 2
- Condition identifier
- EFO:1000710
- Subject identifier
- D017497
- Condition
- Non-alcoholic Fatty Liver Disease
- Highest recorded phase
- 1
- Condition identifier
- EFO:1001249
- Subject identifier
- D065626
- Condition
- Bone Diseases, Metabolic
- Highest recorded phase
- 3
- Condition identifier
- HP:0000938
- Subject identifier
- D001851
- Condition
- Dysmenorrhea
- Highest recorded phase
- 3
- Condition identifier
- HP:0100607
- Subject identifier
- D004412
- Condition
- Metrorrhagia
- Highest recorded phase
- 2
- Condition identifier
- HP:0100608
- Subject identifier
- D008796
- Condition
- Depressive Disorder
- Highest recorded phase
- 2
- Condition identifier
- MONDO:0002050
- Subject identifier
- D003866
- Condition
- Premenstrual Syndrome
- Highest recorded phase
- 2
- Condition identifier
- MONDO:0004169
- Subject identifier
- D011293
And 9 more, listed on the interactive page.
- Condition identifier
- EFO_0000095
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000180
- Highest recorded phase
- 1
- Condition identifier
- EFO_0000195
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000616
- Condition identifier
- EFO_0000660
- Highest recorded phase
- 3
- Condition identifier
- EFO_0000764
- Highest recorded phase
- 1
- Condition identifier
- EFO_0001065
- Condition identifier
- EFO_0002950
- Highest recorded phase
- 2
- Condition identifier
- EFO_0002950
- Highest recorded phase
- 3
- Condition identifier
- EFO_0003882
- Highest recorded phase
- 2
- Condition identifier
- EFO_0003894
- Condition identifier
- EFO_0005279
- Condition identifier
- EFO_0008560
- Condition identifier
- EFO_0009006
- Highest recorded phase
- 2
- Condition identifier
- EFO_0009006
- Highest recorded phase
- 3
- Condition identifier
- EFO_0009008
- Highest recorded phase
- 2
- Condition identifier
- EFO_0009520
- Condition identifier
- EFO_0009520
- Highest recorded phase
- 4
- Condition identifier
- EFO_1000710
- Highest recorded phase
- 2
- Condition identifier
- EFO_1001491
- Condition identifier
- GO_0030728
- Highest recorded phase
- 2
- Condition identifier
- HP_0000132
- Highest recorded phase
- 1
- Condition identifier
- HP_0000739
- Condition identifier
- HP_0000789
- Highest recorded phase
- 3
- Condition identifier
- HP_0000855
And 43 more, listed on the interactive page.
- Event
- abnormal withdrawal bleeding
- Reports
- 72
- Reporting signal score
- 330.342
- Event
- abortion induced
- Reports
- 93
- Reporting signal score
- 198.013
- Event
- application site erythema
- Reports
- 207
- Reporting signal score
- 466.038
- Event
- application site irritation
- Reports
- 146
- Reporting signal score
- 404.007
- Event
- application site pruritus
- Reports
- 211
- Reporting signal score
- 547.712
- Event
- application site rash
- Reports
- 282
- Reporting signal score
- 889.757
- Event
- application site reaction
- Reports
- 162
- Reporting signal score
- 532.312
- Event
- breast tenderness
- Reports
- 95
- Reporting signal score
- 226.041
- Event
- deep vein thrombosis
- Reports
- 1,171
- Reporting signal score
- 2,186.4
- Event
- diarrhoea
- Reports
- 126
- Reporting signal score
- 185.499
- Event
- dysmenorrhoea
- Reports
- 100
- Reporting signal score
- 217.376
- Event
- hot flush
- Reports
- 612
- Reporting signal score
- 1,130.78
- Event
- hypercoagulation
- Reports
- 71
- Reporting signal score
- 189.903
- Event
- incorrect product administration duration
- Reports
- 73
- Reporting signal score
- 183.722
- Event
- intentional medical device removal by patient
- Reports
- 57
- Reporting signal score
- 185.963
- Event
- intracranial venous sinus thrombosis
- Reports
- 66
- Reporting signal score
- 210.029
- Event
- medical device site discomfort
- Reports
- 62
- Reporting signal score
- 224.26
- Event
- meningioma
- Reports
- 113
- Reporting signal score
- 283.626
- Event
- menopausal symptoms
- Reports
- 79
- Reporting signal score
- 245.425
- Event
- menorrhagia
- Reports
- 259
- Reporting signal score
- 443.4
- Event
- menstrual disorder
- Reports
- 58
- Reporting signal score
- 154.844
- Event
- menstruation delayed
- Reports
- 64
- Reporting signal score
- 223.997
- Event
- menstruation irregular
- Reports
- 85
- Reporting signal score
- 203.826
- Event
- metrorrhagia
- Reports
- 505
- Reporting signal score
- 1,501.63
- Event
- migraine
- Reports
- 289
- Reporting signal score
- 252.099
And 15 more, listed on the interactive page.
- NCT00004763
- NCT00033358
- NCT00089414
- NCT00117260
- NCT00191113
- NCT00193726
- NCT00196365
- NCT00212277
- NCT00569244
- NCT00746096
- NCT00902746
- NCT00909857
- NCT01129102
- NCT00254800
- NCT00280657
- NCT00651469
- NCT00656981
- NCT00722761
- NCT00752635
- NCT01466673
- NCT00301587
- NCT00320567
- NCT00320580
- NCT00344383
- NCT00357604
And 31 more, listed on the interactive page.
- Route
- Transdermal
- How often
- Weekly for 3 weeks (21 days), patch-free week every 4 weeks
- Apply new patch each week on the same day of the week
- Do not cut or alter the patch
- Start on Day 1 or Sunday after menstruation
- Use backup contraception for 7 days if starting more than a week after last method
- Wear only one patch at a time
- Hydrogen bond acceptors
- 2
- Hydrogen bond donors
- 2
- Polar surface area
- 40.46
- Calculated partition coefficient (ALogP)
- 3.61
- Calculated partition coefficient (XLogP)
- 3.7
- Prodrug
- No
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 0
- Heavy atoms
- 22
- Molecular formula
- C20H24O2
- Monoisotopic mass
- 296.177630004
- Natural product
- Yes
- 0093-3122
- 0093-7679
- 0378-3340
- 0378-7274
- 0378-7280
- 0480-3472
- 0555-9008
- 0555-9009
- 0555-9010
- 0555-9025
- 0555-9026
- 0555-9027
- 0555-9028
- 16714-029
- 42291-478
- 42291-930
- 49502-627
- 50742-659
- 51285-125
- 51285-127
- 51285-128
- 51285-131
- 59212-146
- 65162-358
- 65162-469
And 27 more, listed on the interactive page.
- Recorded assays
- 5,385
- Active assays
- 315
- Confirmatory
- Other
- Screening
- Summary
- Contraceptives, Oral, Hormonal
- Estrogens
These details could not be displayed.
Related records
Trials (356)
- "E4/DRSP Endocrine Function, Metabolic Control and Hemostasis Study"
- "Effect of CPA/EE Drug on Periodontal Tissue and hsCRP Levels in PCOS Patients With Gingivitis
- "Quick-starting" of a New Combined Hormonal Contraceptive Pills, 15 mg Estetrol/3 mg Drospirenone VS 20 mcg Ethinylestradiol/75 mcg Gestodene Focusing on Ovulation Inhibition
- "Quick-starting" of a Quadriphasic Contraceptive Pills, 1 - 3 mg Estradiol Valerate/ 2 - 3 mg Dienogest VS 20 mcg Ethinylestradiol/75 mcg Gestodene Focusing on Ovulation Inhibition
- 71A/G HSD17B5 SNP and Effects of Oral Contraceptive Pill in PCOS Women
- A Bioequivalence Study of Norgestimate /Ethinyl Estradiol (NGM/EE) Tablets Manufactured at 2 Different Facilities
- A Comparative Pharmacokinetic Study of ORTHO EVRA (a Transdermal Contraceptive Patch) and CILEST (an Oral Contraceptive) in Healthy Female Volunteers
- A Crossover Acceptability Study Assessing a DPP Capsule for HIV and Pregnancy Prevention
- A Dose-Finding Study to Evaluate Ovarian Function and Vaginal Bleeding in Next Generation Rings (P06109/MK-8175A/MK-8342B-012)
- A Drug Drug Interaction Study Between PF-06826647 And Oral Contraceptive Steroids In Healthy Female Participants
- A Drug Interaction Study of BIIB074 and an Oral Contraceptive Regimen
- A Drug Interaction Study of Danicopan
- A Drug Interaction Study of Folic Acid and Oral Contraceptive Tablets Containing Norgestimate (NGM) /Ethinyl Estradiol (EE) in Healthy Women.
- A Drug Interaction Study of Folic Acid and Oral Contraceptive Tablets Containing Norgestimate (NGM)/Ethinyl Estradiol (EE) in Healthy Women.
- A Drug-drug Interaction Study Between BMS-663068 and Oral Contraceptives in Healthy Female Volunteers (DDI)
- A Drug-Drug Interaction Study Between HS-10374 Tablets and Drospirenone and Ethinyl Estradiol Tablets(Yasmin®)
- A Drug-Drug Interaction Study of MK 8527 With a Combined Oral Contraceptive (LNG/EE)
- A Drug-drug Interaction Study of Vorasidenib and a Combined Oral Contraceptive in Healthy Female Participants
- A Drug-Drug Interaction Study to Assess the Effect of Trametinib on the Pharmacokinetics of an Oral Contraceptive in Female Patients With Solid Tumors
- A Drug-drug Interaction Study to Evaluate the Effects of Pelabresib on the Pharmacokinetics of Repaglinide, Midazolam, and Combined Oral Contraceptive in Patients With Advanced Malignancies
Approved for (3)
In development for (28)
- Amenorrhea Phase 3
- Anorexia nervosa Phase 3
- B-cell chronic lymphocytic leukemia Phase 1
- Binge eating disorder Phase 2
- Breast cancer Phase 3
- Bulimia nervosa Phase 2
- Chronic hepatitis B virus infection Phase 1
- Chronic hepatitis C virus infection Phase 1
- Cystic fibrosis Phase 1
- Depressive disorder Phase 2
- Dysmenorrhea Phase 3
- Endometrial cancer Phase 2
- Endometriosis Phase 3
- Female infertility Phase 1
- Hepatitis C virus infection Phase 1
- Hidradenitis suppurativa Phase 2
- HIV infectious disease Phase 1
- Metabolic bone disorder Phase 3
- Metabolic dysfunction-associated steatohepatitis Phase 1
- Migraine disorder Phase 3
Other linked conditions (2)
- Periodontal disorder
- Temporomandibular joint disorder
Targets (1)
- ESR1 Estrogen receptor alpha agonist