Product Name

Ethinyl Estradiol

CAS Number

57-63-6

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Product Name:
Ethinyl Estradiol
CAS Number:
57-63-6
Indication:
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.
Mode of Action:

Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. This cascade is initiated by initially binding to the estrogen receptors. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).

Pharmacodynamics:

Ethinyl estradiol is a synthetic derivative of the natural estrogen estradiol. It is one of two estrogens currently used in oral contraceptive pills. The other, mestranol, is converted to ethinyl estradiol before it is biologically active. Ethinyl estradiol and norethindrone are used together as an oral contraceptive agent.

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.

Toxicity:

Oral, mouse LD50: 1737 mg/kg. Symptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.

IUPAC:
(1S, 10R, 11S, 14R, 15S)-14-ethynyl-15-methyltetracyclo[8.7.0.0, {2, 7}.0, {11, 15}]heptadeca-2(7), 3, 5-triene-5, 14-diol
ATC:
G03CA01
PubChem:
5991
DrugBank:
DB00977 (APRD00691)
Formula:
C12H16F3N
Molecular Mass:
296.4034
Synonyms:
17 alpha-Ethinylestradiol 17 alpha-Ethynylestradiol 17 alpha-Ethynyloestradiol 17-ethinyl-3,17-estradiol 17-ethinyl-3,17-oestradiol 17-ethinylestradiol 17alpha-Ethinyl estradiol 17_-ethynylestradiol Ethinyl-Oestranol Ethinylestradiol Ethinylestradiolum [INN-Latin] Ethinylestriol Ethinyloestradiol Ethynyl estradiol Ethynylestradiol Ethynyloestradiol Etinilestradiol [INN-Spanish]
SMILES:
C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(O)=C4)[C@@H]1CC[C@@]2(O)C#C
InChi:
BFPYWIDHMRZLRN-SLHNCBLASA-N

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