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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H24O2
Molecular Weight 296.4034
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHINYL ESTRADIOL

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C=C4

InChI

InChIKey=BFPYWIDHMRZLRN-SLHNCBLASA-N
InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H24O2
Molecular Weight 296.4034
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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. 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). Used 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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
LESSINA-21

Cmax

ValueDoseCo-administeredAnalytePopulation
122.8 pg/mL
0.06 mg single, oral
ETHINYL ESTRADIOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1335.8 pg × h/mL
0.06 mg single, oral
ETHINYL ESTRADIOL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
17.5 h
0.06 mg single, oral
ETHINYL ESTRADIOL plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Endometriosis Ethinyl estradiol-levonorgestrel products are packaged in 21 or 28 day dosage preparations. The last seven tablets in 28 day dosage preparations are hormonally inert. Regardless of the number of tablets in a package, the cycle length for oral contraceptives is generally considered to be 28 days.
Route of Administration: Oral
In Vitro Use Guide
EE (
Substance Class Chemical
Record UNII
423D2T571U
Record Status Validated (UNII)
Record Version