Ethinylestradiol

Estrogen — GENITO URINARY SYSTEM AND SEX HORMONES

Key facts

Ethinylestradiol is an ofp drug in the Estrogen class catalogued in DrugCentral. It was first approved by the FDA in 1943. Its mechanism of action is classified as Estrogen Receptor Agonists. DrugCentral lists 22 molecular targets, including ESR1, ESR2 and SLC6A4. Recorded indications include Acne vulgaris, Atrophic vaginitis, Atrophic vulva and Contraception.

• Approval status: ofp (first approved 1943 by the FDA).
• Drug class: Estrogen.
• Mechanism of action: Estrogen Receptor Agonists.
• Molecular targets: ESR1, ESR2, SLC6A4 and AR (22 listed in DrugCentral).
• Indications: Acne vulgaris, Atrophic vaginitis, Atrophic vulva, Contraception and Controlled ovarian stimulation and others.
• ATC code: G03AA01 (Progestogens and estrogens, fixed combinations).
• Molecular formula: C20H24O2; molecular weight 296.41 g/mol.

Indications & contraindications

Drug–disease relationships curated by DrugCentral (OMOP / SNOMED concepts).

Indications (9)

• Acne vulgaris
• Atrophic vaginitis
• Atrophic vulva
• Contraception
• Controlled ovarian stimulation
• Dysmenorrhea
• Menopausal flushing
• Postmenopausal osteoporosis
• Premenstrual dysphoric disorder

Off-label uses (6)

• Abnormal uterine bleeding unrelated to menstrual cycle
• Amenorrhea
• Female hypogonadism syndrome
• Menorrhagia
• Polycystic ovaries
• Postcoital contraception

Contraindications (78)

• Acute nephropathy
• Adrenal cortical hypofunction
• Angina pectoris
• Asthma
• Bed-ridden
• Benign Hepatic Cell Adenoma
• Benign mammary dysplasia
• Benign prostatic hyperplasia
• Body fluid retention
• Breast Carcinoma in Males
• Breast lump
• Breastfeeding (mother)
• Carcinoma of female breast
• Cardiovascular event risk
• Cerebrovascular accident
• Chloasma
• Cholestasis of pregnancy
• Chorea
• Chronic heart failure
• Deep venous thrombosis
• Dementia
• Depressive disorder
• Diabetes mellitus
• Diabetes with Vascular Disease Complication
• Diplopia
• Disease of liver
• Disorder of coronary artery
• Disorder of gallbladder
• Edema
• Endometrial carcinoma
• + 48 more

Mechanism & targets

• Mechanism of action (MoA): Estrogen Receptor Agonists
• Established pharmacologic class: Estrogen

Molecular targets (22)

Target	Gene	Action	Activity
Estrogen receptor	ESR1	agonist	Kd 9.83
Estrogen receptor beta	ESR2	unknown	IC50 8.09
Sodium-dependent serotonin transporter	SLC6A4	unknown	Ki 7.54
Androgen receptor	AR	unknown	IC50 7.30
Progesterone receptor	PGR	unknown	Ki 6.86
Sex hormone-binding globulin	SHBG	unknown	Kd 6.81
Sodium-dependent dopamine transporter	SLC6A3	unknown	Ki 6.35
Aldehyde oxidase	AOX1	unknown	IC50 6.24
Glucocorticoid receptor	NR3C1	unknown	Ki 6.11
Sodium-dependent noradrenaline transporter	SLC6A2	unknown	Ki 6.02
5-hydroxytryptamine receptor 4	HTR4	unknown	Ki 5.88
Solute carrier family 22 member 2	SLC22A2	unknown	IC50 5.66
Nuclear receptor subfamily 1 group I member 3	NR1I3	unknown	IC50 5.52
Arachidonate 15-lipoxygenase	ALOX15	unknown	IC50 5.25
Androgen receptor	Ar	unknown	IC50 5.09
Kappa-type opioid receptor	OPRK1	unknown	Ki 4.99
Mu-type opioid receptor	OPRM1	unknown	Ki 4.96
Adenosine receptor A2a	ADORA2A	unknown	Ki 4.93
Adenosine receptor A3	ADORA3	unknown	Ki 4.73
Multidrug and toxin extrusion protein 2	SLC47A2	unknown	IC50 4.69

Regulatory approvals (2)

Date	Agency	Marketed as	Applicant	Orphan
2010-07-23	PMDA	—	Bayer Yakuhin
1943-06-25	FDA	—	SCHERING

ATC classification

ATC code	Therapeutic hierarchy
G03AA01	GENITO URINARY SYSTEM AND SEX HORMONES › SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM › HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE › Progestogens and estrogens, fixed combinations
G03AA02	GENITO URINARY SYSTEM AND SEX HORMONES › SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM › HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE › Progestogens and estrogens, fixed combinations
G03AA03	GENITO URINARY SYSTEM AND SEX HORMONES › SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM › HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE › Progestogens and estrogens, fixed combinations
G03AA04	GENITO URINARY SYSTEM AND SEX HORMONES › SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM › HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE › Progestogens and estrogens, fixed combinations
G03AA05	GENITO URINARY SYSTEM AND SEX HORMONES › SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM › HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE › Progestogens and estrogens, fixed combinations
G03AA06	GENITO URINARY SYSTEM AND SEX HORMONES › SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM › HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE › Progestogens and estrogens, fixed combinations
G03AA07	GENITO URINARY SYSTEM AND SEX HORMONES › SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM › HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE › Progestogens and estrogens, fixed combinations
G03AA08	GENITO URINARY SYSTEM AND SEX HORMONES › SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM › HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE › Progestogens and estrogens, fixed combinations
G03AA09	GENITO URINARY SYSTEM AND SEX HORMONES › SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM › HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE › Progestogens and estrogens, fixed combinations
G03AA10	GENITO URINARY SYSTEM AND SEX HORMONES › SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM › HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE › Progestogens and estrogens, fixed combinations

Reported adverse-event signals

Strongest FDA FAERS disproportionality signals (log-likelihood ratio). A signal is a statistical association in spontaneous reports, not proof that the drug causes the event.

MedDRA term	LLR
Unintended pregnancy	708.3
Pulmonary embolism	682.4
Intermenstrual bleeding	622.4
Device expulsion	538.5
Deep vein thrombosis	355.9
Pregnancy with contraceptive device	305.1
No adverse event	272.8
Incorrect product administration duration	251.0
Inappropriate schedule of product administration	226.7
Medical device discomfort	207.5
Product quality issue	167.5
Heavy menstrual bleeding	165.7

Chemical structure

Full physicochemical, ADMET and 3D-structure analysis of Ethinylestradiol is on its molecule page.

• Molecular formula: C₂₀H₂₄O₂
• Molecular weight: 296.41 g/mol
• CAS number: 57-63-6
• InChIKey: BFPYWIDHMRZLRN-SLHNCBLASA-N
• PubChem CID: 5991

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

Frequently asked questions

Answers are generated from the structured data on this page, not written by hand.

What is Ethinylestradiol used for?

DrugCentral lists the following indications for Ethinylestradiol: Acne vulgaris, Atrophic vaginitis, Atrophic vulva, Contraception, Controlled ovarian stimulation, Dysmenorrhea, Menopausal flushing and Postmenopausal osteoporosis and others.

How does Ethinylestradiol work?

Ethinylestradiol is classified as Estrogen Receptor Agonists; its molecular targets in DrugCentral include ESR1 (agonist), ESR2, SLC6A4 and AR.

When was Ethinylestradiol first approved?

Ethinylestradiol was first approved by the FDA in 1943.

What drug class does Ethinylestradiol belong to?

Ethinylestradiol is in the Estrogen class.

What is the chemical formula of Ethinylestradiol?

Ethinylestradiol has the molecular formula C20H24O2 and a molecular weight of 296.41 g/mol.

Sources

• DrugCentral drug card 1082 — structure, indications, targets, approvals, pharmacologic classes (CC BY-SA 4.0)
• ChEMBL CHEMBL691 — compound record and bioactivity
• PubChem CID 5991 — chemical identifiers
• DrugBank DB00977 — drug record
• FDA UNII 423D2T571U — substance identity
• DailyMed: FDA labels for Ethinylestradiol — current prescribing information (label search)
• UniProt P03372 (ESR1) — target protein
• UniProt Q92731 (ESR2) — target protein
• UniProt P31645 (SLC6A4) — target protein
• UniProt P10275 (AR) — target protein
• UniProt P04278 (SHBG) — target protein
• UniProt Q01959 (SLC6A3) — target protein
• FDA Adverse Event Reporting System (openFDA FAERS) — adverse-event signals, as aggregated by DrugCentral

How this page is built: methodology · editorial policy & corrections.