Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H26O2 |
Molecular Weight | 298.4192 |
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])CC(=O)CC4
InChI
InChIKey=ICTXHFFSOAJUMG-SLHNCBLASA-N
InChI=1S/C20H26O2/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/h1,16-18,22H,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12475720Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12475720
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12475720
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12475720
Norethynodrel is a steroidal progestin of the 19-nortestosterone group and an isomer of norethisterone. Norethynodrel is a progesteron agonist with very weak estrogenic activiry. Noretynodrel was introduced in 1957 in Enovid, a combination formulation of noretynodrel and mestranol, for the treatment of gynecological and menstrual disorders.A few years later, in May 1960, Enovid was also approved as the first oral contraceptive.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12475720 |
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 Date-2.78207988E11 |
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Primary | ENOVID Approved UseMenstrual disorder Launch Date-2.78207988E11 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
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76 min |
single, intravenous |
NORETHYNODREL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
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5% |
NORETHYNODREL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: MALE food status: UNKNOWN |
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5% |
NORETHYNODREL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p.122 |
healthy, 25 n = 1 Health Status: healthy Condition: Contraception Age Group: 25 Sex: F Population Size: 1 Sources: Page: p.122 |
Disc. AE: Thromboembolic event... AEs leading to discontinuation/dose reduction: Thromboembolic event Sources: Page: p.122 |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Thromboembolic event | Disc. AE | 20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p.122 |
healthy, 25 n = 1 Health Status: healthy Condition: Contraception Age Group: 25 Sex: F Population Size: 1 Sources: Page: p.122 |
PubMed
Title | Date | PubMed |
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[Correlative changes of histomorphometry and biomechanical property of lumbar vertebrae body in ovariectomized rats]. | 2004 Apr |
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The involvement of CYP3A4 and CYP2C9 in the metabolism of 17 alpha-ethinylestradiol. | 2004 Nov |
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Removal of estrogenic activity and formation of oxidation products during ozonation of 17alpha-ethinylestradiol. | 2004 Oct 1 |
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Developmental effects of prenatal exposure to bisphenol a on the uterus of rat offspring. | 2004 Sep-Oct |
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Bioaccumulation of 14C-17alpha-ethinylestradiol by the aquatic oligochaete Lumbriculus variegatus in spiked artificial sediment. | 2005 Apr |
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Relationship between ethinylestradiol-mediated changes in endocrine function and reproductive impairment in Japanese medaka (Oryzias latipes). | 2005 Feb |
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p-Toluenesulfonyl isocyanate as a novel derivatization reagent to enhance the electrospray ionization and its application in the determination of two stereo isomers of 3-hydroxyl-7-methyl-norethynodrel in plasma. | 2005 Jan 25 |
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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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Can 19-nortestosterone derivatives be aromatized in the liver of adult humans? Are there clinical implications? | 2007 Aug |
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Benefits and risks of hormonal contraception for women. | 2007 Aug 10 |
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Suppression of the inflammatory response in experimental arthritis is mediated via estrogen receptor alpha but not estrogen receptor beta. | 2010 |
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The lowest-dose, extended-cycle combined oral contraceptive pill with continuous ethinyl estradiol in the United States: a review of the literature on ethinyl estradiol 20 μg/levonorgestrel 100 μg + ethinyl estradiol 10 μg. | 2010 Aug 10 |
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Clinically relevant progestins regulate neurogenic and neuroprotective responses in vitro and in vivo. | 2010 Dec |
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/12475720
For transactivation studies CHO cells stably transfected with hER-RO-LUC, hER-RO-LUC, hAR-MMTVLUC, hPR-B-MMTV-LUC, hPR-A-MMTV-LUC or hGRMMTV-LUC were used. 5 × 104 cells/well were seeded into a 96-well plate and incubated with compounds (final ethanol content: 1% v/v) for 16 h in medium with 5% charcoal-treated supplemented defined bovine calf serum at 37°C in a humidified atmosphere of air supplemented with 5% CO2. Of the total 250uL incubation volume, 200 uLl was removed, and 50 uL LucLite was added for cell lysis and luciferase measurement. Luciferase activity was measured in a Topcount luminescence counter (Canberra Packard). Relative agonistic activity (RAA) studies were carried out with various concentrations of the standards (1:2:4 dilutions) and compounds of interest. The RAA was determined to Org 2058 (PRA and PRB). Full agonistic curves for PRA, PRB were also determined in the CHO cells described before. The concentrations of the compounds used were 10−5 to 10−12 mol/l with a dilution factor of 3.16. Norethynodrel displayed agonistic activity with respect to PRA with EC50 of 10 nM, and PRB with EC50 of below 1 nM.
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QG03FA09
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WHO-ATC |
G03FA09
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NCI_THESAURUS |
C776
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88181ACA0M
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15432
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M8057
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SUB14666MIG
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DB09371
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1965
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D009641
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NORETHYNODREL
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DTXSID3021069
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200-682-1
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2951
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68-23-5
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CHEMBL1387
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7515
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SUB12439MIG
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1257
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C66244
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Norethynodrel
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE TOXIC (PARENT)