Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H26O2 |
Molecular Weight | 310.4299 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(OC)C=C4
InChI
InChIKey=IMSSROKUHAOUJS-MJCUULBUSA-N
InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/536998 |
15.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | ENOVID Approved UseCombination oral contraceptives inhibit ovulation via a negative feedback mechanism on the hypothalamus, which alters the normal pattern of gonadotropin secretion of a follicle-stimulating hormone (FSH) and luteinizing hormone by the anterior pituitary. The follicular phase FSH and midcycle surge of gonadotropins are inhibited. In addition, combination hormonal contraceptives produce alterations in the genital tract, including changes in the cervical mucus, rendering it unfavorable for sperm penetration even if ovulation occurs. Changes in the endometrium may also occur, producing an unfavorable environment for nidation. Combination hormonal contraceptive drugs may alter the tubal transport of the ova through the fallopian tubes. Progestational agents may also alter sperm fertility. Launch Date1961 |
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Primary | ENOVID Approved UseMenstrual disorder |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
175 pg/mL |
50 μg single, oral dose: 50 μg route of administration: Oral experiment type: SINGLE co-administered: |
ETHINYL ESTRADIOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
963 pg × min/mL |
50 μg single, oral dose: 50 μg route of administration: Oral experiment type: SINGLE co-administered: |
ETHINYL ESTRADIOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6 h |
50 μg single, oral dose: 50 μg route of administration: Oral experiment type: SINGLE co-administered: |
ETHINYL ESTRADIOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | yes (pharmacogenomic study) Comment: majority of tested variants exhibited decreased clearance values compared to wild type, except for CYP2C9*40 and *36 |
PubMed
Title | Date | PubMed |
---|---|---|
Letter: Oral contraceptives and malignant hepatoma. | 1976 Feb 28 |
|
Asymptomatic liver cell adenomas. Another case of resolution after discontinuation of oral contraceptive use. | 1978 Apr 21 |
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Hormone replacement treatment and benign intracranial hypertension. | 1982 Jun 5 |
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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities. | 2012 Nov 19 |
Patents
Sample Use Guides
Dose starts on first day of menstrual cycle taking 1 tablet daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/536998
In vitro estrogen receptor binding affinity was determined using uterine cytosol preparation. Reaction mixture contained 0.7 ug of protein from the receptor preparation and 16000 dpm of 17beta[3H]estradiol in 0.25 mL of 0.01 Tris-HCl buffer, pH 8.0, containing 0.001 M EDTA and 0.25 M sucrose. Compound was tested in a dose-response fashion using 8 concentration from 0.1 nM to 100 000 nM in duplicate. After incubation at 4°C for 16-18 h, the compounds bound to the receptor were separated from those free in solution using dextran-coated charcoal. The amount of radioactivity bound to the receptor was quantified in Aquasol using liquid scintillation spectrometer. Mestranol did not bound to estrogen receptor in concetrations up to 100 uM, but its metabolite displaced estradiol with IC50 of 15 nM.
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000000100
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NCI_THESAURUS |
C478
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NDF-RT |
N0000175825
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EPA PESTICIDE CODE |
115401
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LIVERTOX |
607
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72-33-3
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MESTRANOL
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1394008
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3588
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6784
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B2V233XGE7
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100000081168
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7087
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DTXSID0020814
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6782
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1714
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SUB08791MIG
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1139
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84032
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C636
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6291
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DB01357
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D008656
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m7257
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CHEMBL1201151
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200-777-8
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METABOLITE ACTIVE (PRODRUG)
SUBSTANCE RECORD