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
Molecular Formula | C20H26O2 |
Molecular Weight | 298.4192 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 5 / 5 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 |
---|---|---|---|---|
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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[Effect of tibolone on vascular markers of human female coronary arteries - comparison with estradiol/norethisterone]. | 2001 Nov |
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Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003 Oct |
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The involvement of CYP3A4 and CYP2C9 in the metabolism of 17 alpha-ethinylestradiol. | 2004 Nov |
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The estrogenic activity of synthetic progestins used in oral contraceptives enhances fatty acid synthase-dependent breast cancer cell proliferation and survival. | 2005 Jun |
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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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Postmenopausal tibolone therapy: biologic principles and applied clinical practice. | 2007 Jan 3 |
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New low-dose, extended-cycle pills with levonorgestrel and ethinyl estradiol: an evolutionary step in birth control. | 2010 Aug 9 |
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Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein. | 2015 Feb |
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.
Substance Class |
Chemical
Created
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Record UNII |
88181ACA0M
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Record Status |
Validated (UNII)
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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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100000089985
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SUB14666MIG
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D009641
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NORETHYNODREL
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CHEMBL1387
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SUB12439MIG
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C66244
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Norethynodrel
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
Metabolite to parent drug ratio in non-uraemic human plasma.
Norethynodrel is metabolized in man to the antifertility agent norethisterone(norethindrone).
METABOLITE TO PARENT DRUG RATIO
PLASMA; URINE
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METABOLITE TOXIC -> PARENT |
The metabolite was implicated in production of delayed coma after methsuximide overdose in man.
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METABOLITE TOXIC -> PARENT |
The metabolite produced ataxia in man.
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METABOLITE -> PARENT |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |