Definition
A semisynthetic alkylated ESTRADIOL with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally, and is often used as the estrogenic component in ORAL CONTRACEPTIVES.
A synthetic form of estradiol, called ethinyl estradiol is a major component of hormonal contraceptive devices.
Description
A semisynthetic alkylated estradiol with a 17-alpha-ethinyl substitution. It has high estrogenic potency when administered orally and is often used as the estrogenic component in oral contraceptives . Ethinyl estradiol is marketed mostly as a combination oral contraceptive under several brand names such as Alesse, Tri-Cyclen, Triphasil, and Yasmin. The FDA label includes a black box warning that states that combination oral contraceptives should not be used in women over 35 years old who smoke due to the increased risk of serious cardiovascular side effects.
Top Gene Interactions
Related Pathways
General Information
- Metabolism: Hepatic. Quantitatively, the major metabolic pathway for ethinyl estradiol, both in rats and in humans, is aromatic hydroxylation, as it is for the natural estrogens. Half Life: 36 +/- 13 hours
- Uses/Sources: For treatment of moderate to severe vasomotor symptoms associated with the menopause, female hypogonadism, prostatic carcinoma-palliative therapy of advanced disease, breast cancer, as an oral contraceptive, and as emergency contraceptive.
- Symptoms: Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females. The FDA label includes a black box warning that states that combination oral contraceptives with ethinyl estradiol should not be used in women over 35 years old who smoke due to the increased risk of serious cardiovascular side effects.
- Route of Exposure: Rapid and complete absorption follows oral intake of ethinyl estradiol (bioavailability 43%).
Toxicity
- Carcinogenicity: No indication of carcinogenicity to humans (not listed by IARC).
- Toxicity: Oral, mouse LD<sub>50</sub>: 1737 mg/kg.
Mechanism of Action
Target Name | Mechanism of Action | References |
---|---|---|
Estrogen receptor Glucocorticoid receptor Estrogen receptor beta Androgen receptor Progesterone receptor Cytochrome P450 3A5 Nuclear receptor subfamily 1 group I member 2 Sodium-dependent serotonin transporter Sodium-dependent dopamine transporter Translocator protein Sodium-dependent noradrenaline transporter Cytochrome P450 2C9 Cytochrome P450 2C19 Nuclear receptor subfamily 1 group I member 3 Cytochrome P450 2C18 Cytochrome P450 2J2 Bile acid receptor |
23611293 |