Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H30O3 |
Molecular Weight | 354.4825 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1CC[C@@]2(OC(C)=O)C#C
InChI
InChIKey=YDQDJLTYVZAOQX-GOMYTPFNSA-N
InChI=1S/C23H30O3/c1-4-22-12-10-19-18-9-7-17(25)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)26-15(3)24/h2,14,18-21H,4,6-13H2,1,3H3/t18-,19+,20+,21-,22-,23-/m0/s1
Molecular Formula | C23H30O3 |
Molecular Weight | 354.4825 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.drugbank.ca/drugs/DB09389 | https://www.drugs.com/drp/norgestrel.html | https://www.ncbi.nlm.nih.gov/pubmed/8136310http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021225s031lbl.pdfCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25698840
Sources: https://www.drugbank.ca/drugs/DB09389 | https://www.drugs.com/drp/norgestrel.html | https://www.ncbi.nlm.nih.gov/pubmed/8136310http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021225s031lbl.pdf
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25698840
Levonorgestrel (LNG) is a synthetic progestational hormone with actions similar to those of progesterone and about twice as potent as its racemic or (+-)-isomer (norgestrel). It is used for contraception, control of menstrual disorders, and treatment of endometriosis. It is usually supplied in a racemic mixture (Norgestrel, 6533-00-2). Only the levonorgestrel isomer is active. Within an Intrauterine device (IUD), sold as Mirena among others, it is effective for long term prevention of pregnancy. The local mechanism by which continuously released LNG enhances contraceptive effectiveness of Mirena has not been conclusively demonstrated. Studies of Mirena and similar LNG IUS prototypes have suggested several mechanisms that prevent pregnancy: thickening of cervical mucus preventing passage of sperm into the uterus, inhibition of sperm capacitation or survival, and alteration of the endometrium. Mirena has mainly local progestogenic effects in the uterine cavity. The high local levels of levonorgestrel lead to morphological changes including stromal pseudodecidualization, glandular atrophy, a leukocytic infiltration and a decrease in glandular and stromal mitoses. Ovulation is inhibited in some women using Mirena. In a 1-year study, approximately 45% of menstrual cycles were ovulatory, and in another study after 4 years, 75% of cycles were ovulatory. There has been much debate regarding levonorgestrel emergency contraception's (LNG-EC's) method of action since 1999 when the Food and Drug Administration first approved its use. Proponents of LNG-EC have argued that they have moral certitude that LNG-EC works via a non-abortifacient mechanism of action, and claim that all the major scientific and medical data consistently support this hypothesis. However, newer medical data serve to undermine the consistency of the non-abortifacient hypothesis and instead support the hypothesis that preovulatory administration of LNG-EC has significant potential to work via abortion. The implications of the newer data have important ramifications for medical personnel, patients, and both Catholic and non-Catholic emergency room protocols. In the future, technology such as the use of early pregnancy factor may have the potential to quantify how frequently preovulatory LNG-EC works via abortion. The latest scientific and medical evidence now demonstrates that levonorgestrel emergency contraception theoretically works via abortion quite often. The implications of the newer data have important ramifications for medical personnel, patients, and both Catholic and non-Catholic emergency room rape protocols.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3139361 |
|||
Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3139361 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | MIRENA Approved UseMirena is indicated for intrauterine contraception for up to 5 years. Mirena is also indicated for the treatment of heavy menstrual bleeding in women who choose to use intrauterine contraception as their method of contraception. Mirena is recommended for women who have had at least one child. The system should be replaced after 5 years if continued use is desired. Launch Date2000 |
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Primary | MIRENA Approved UseMirena is indicated for intrauterine contraception for up to 5 years. Mirena is also indicated for the treatment of heavy menstrual bleeding in women who choose to use intrauterine contraception as their method of contraception. Mirena is recommended for women who have had at least one child. The system should be replaced after 5 years if continued use is desired. Launch Date2000 |
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Sources: https://www.drugs.com/drp/norgestrel.html |
Preventing | OVRETTE Approved UseProgestin-only oral contraceptives are indicated for the prevention of pregnancy. Launch Date1973 |
||
Sources: https://www.drugs.com/pro/elinest.html |
Preventing | ELINEST Approved UseOral contraceptives are indicated for the prevention of pregnancy in women who elect to use oral contraceptives as a method of contraception. Launch Date2012 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.11 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12169384 |
0.75 mg single, oral dose: 0.75 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVONORGESTREL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
16.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30703352 |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVONORGESTREL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
123.1 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12169384 |
0.75 mg single, oral dose: 0.75 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVONORGESTREL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
360.1 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30703352 |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVONORGESTREL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
24.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12169384 |
0.75 mg single, oral dose: 0.75 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVONORGESTREL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
29.7 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30703352 |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVONORGESTREL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
20 ug 1 times / day multiple, intrauterine Recommended Dose: 20 ug, 1 times / day Route: intrauterine Route: multiple Dose: 20 ug, 1 times / day Sources: |
healthy, 16-45 |
Disc. AE: Bleeding... AEs leading to discontinuation/dose reduction: Bleeding (1.5%) Sources: |
20 ug 1 times / day multiple, intrauterine Recommended Dose: 20 ug, 1 times / day Route: intrauterine Route: multiple Dose: 20 ug, 1 times / day Sources: |
healthy, 27.3 ± 5.7 |
Disc. AE: Menstrual irregularity, Amenorrhea... AEs leading to discontinuation/dose reduction: Menstrual irregularity (0.7%) Sources: Amenorrhea (0.06%) |
90 ug 1 times / day multiple, oral Recommended Dose: 90 ug, 1 times / day Route: oral Route: multiple Dose: 90 ug, 1 times / day Sources: |
healthy, 27.6±6.7 |
Disc. AE: Metrorrhagia, Bleeding vaginal... AEs leading to discontinuation/dose reduction: Metrorrhagia (8.7%) Sources: Bleeding vaginal (3.7%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Bleeding | 1.5% Disc. AE |
20 ug 1 times / day multiple, intrauterine Recommended Dose: 20 ug, 1 times / day Route: intrauterine Route: multiple Dose: 20 ug, 1 times / day Sources: |
healthy, 16-45 |
Amenorrhea | 0.06% Disc. AE |
20 ug 1 times / day multiple, intrauterine Recommended Dose: 20 ug, 1 times / day Route: intrauterine Route: multiple Dose: 20 ug, 1 times / day Sources: |
healthy, 27.3 ± 5.7 |
Menstrual irregularity | 0.7% Disc. AE |
20 ug 1 times / day multiple, intrauterine Recommended Dose: 20 ug, 1 times / day Route: intrauterine Route: multiple Dose: 20 ug, 1 times / day Sources: |
healthy, 27.3 ± 5.7 |
Bleeding vaginal | 3.7% Disc. AE |
90 ug 1 times / day multiple, oral Recommended Dose: 90 ug, 1 times / day Route: oral Route: multiple Dose: 90 ug, 1 times / day Sources: |
healthy, 27.6±6.7 |
Metrorrhagia | 8.7% Disc. AE |
90 ug 1 times / day multiple, oral Recommended Dose: 90 ug, 1 times / day Route: oral Route: multiple Dose: 90 ug, 1 times / day Sources: |
healthy, 27.6±6.7 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203159Orig1s000ClinPharmR.pdf#page=17 Page: (ClinPharm) 17 |
likely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203159Orig1s000ClinPharmR.pdf#page=17 Page: (ClinPharm) 17 |
likely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203159Orig1s000ClinPharmR.pdf#page=17 Page: (ClinPharm) 17 |
likely | |||
major | yes (co-administration study) Comment: Concomitant administration of efavirenz (moderate CYP3A inducer) has been found to reduce plasma levels of levonorgestrel (AUC) by around 50%. Page: (ClinPharm) 16-17 |
|||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203159Orig1s000ClinPharmR.pdf#page=17 Page: (ClinPharm) 17 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203159Orig1s000ClinPharmR.pdf#page=17 Page: (ClinPharm) 17 |
unlikely |
PubMed
Title | Date | PubMed |
---|---|---|
Rat uterine complement C3 expression as a model for progesterone receptor modulators: characterization of the new progestin trimegestone. | 2001 Aug |
|
Influence of two low-dose oral contraceptives on pulsatile gonadotropin secretion. | 2001 Aug |
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Etonogestrel implant (Implanon) for contraception. | 2001 Aug |
|
Combined oral hormone replacement therapy formulations. | 2001 Aug |
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Preclinical profiles of progestins used in formulations of oral contraceptives and hormone replacement therapy. | 2001 Aug |
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Over-the-counter advice for genital problems: the role of the community pharmacist. | 2001 Aug |
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Treatment of menorrhagia with the levonorgestrel intrauterine system versus endometrial resection. | 2001 Aug |
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The relation of oxidized LDL autoantibodies and long-term hormone replacement therapy to ultrasonographically assessed atherosclerotic plaque quantity and severity in postmenopausal women. | 2001 Aug |
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[Hormonal contraception with gestagens]. | 2001 Aug 20 |
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Fine structure of prolactin cell of female albino rat as affected by some antifertility drugs--a comparative electron microscopic study. | 2001 Feb |
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A prospective study of the effects of oral contraceptives on sexuality and well-being and their relationship to discontinuation. | 2001 Jul |
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Levonorgestrel concentrations during 7 years of continuous use of Jadelle contraceptive implants. | 2001 Jul |
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Use of Norplant implants in the immediate postpartum period among asymptomatic HIV-1-positive mothers. | 2001 Jul |
|
Young women requesting emergency contraception are, despite contraceptive counseling, a high risk group for new unintended pregnancies. | 2001 Jul |
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Levonorgestrel-only emergency contraception: real-world tolerance and efficacy. | 2001 Jul |
|
Effects of two low-dose oral contraceptives containing ethinylestradiol and either desogestrel or levonorgestrel on serum lipids and lipoproteins with particular regard to LDL size. | 2001 Jul |
|
Multicenter, comparative study of cycle control, efficacy and tolerability of two low-dose oral contraceptives containing 20 microg ethinylestradiol/100 microg levonorgestrel and 20 microg ethinylestradiol/500 microg norethisterone. | 2001 Jul |
|
Norgestimate. From the laboratory to three clinical indications. | 2001 Jul |
|
The management of menorrhagia--SMART study (Satisfaction with Mirena and Ablation: a Randomised Trial). | 2001 Jul |
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Levonorgestrel-releasing (20mcg/day) intrauterine systems (Mirena) compared with other methods of reversible contraceptives. | 2001 Jul |
|
A village would be nice but...it takes a long-acting contraceptive to prevent repeat adolescent pregnancies. | 2001 Jul |
|
Third generation oral contraceptives and risk of venous thrombosis: meta-analysis. | 2001 Jul 21 |
|
Evaluation of genotoxic potential of synthetic progestins-norethindrone and norgestrel in human lymphocytes in vitro. | 2001 Jul 25 |
|
The roles of estrogen and progestin in producing deciduosarcoma and other lesions in the rabbit. | 2001 Jul-Aug |
|
The development and regression of deciduosarcomas and other lesions caused by estrogens and progestins in rabbits. | 2001 Jul-Aug |
|
Weight change and adverse event incidence with a low-dose oral contraceptive: two randomized, placebo-controlled trials. | 2001 Jun |
|
Comparison of a novel norgestimate/ethinyl estradiol oral contraceptive (Ortho Tri-Cyclen Lo) with the oral contraceptive Loestrin Fe 1/20. | 2001 Jun |
|
Treatment of menorrhagia with a novel 'frameless' intrauterine levonorgestrel-releasing drug delivery system: a pilot study. | 2001 Jun |
|
The effects of two progrestogen-only pills containing either desogestrel (75 microgram/day) or levonorgestrel (30 microgram/day) on carbohydrate metabolism and adrenal and thyroid function. | 2001 Jun |
|
The need for more active promotion of emergency contraception. | 2001 Jun |
|
Hormonal and barrier methods of contraception, oncogenic human papillomaviruses, and cervical squamous intraepithelial lesion development. | 2001 Jun |
|
Protein S levels are lower in women receiving desogestrel-containing combined oral contraceptives (COCs) than in women receiving levonorgestrel-containing COCs at steady state and on cross-over. | 2001 Jun |
|
Treatment of menorrhagia. | 2001 Jun 9 |
|
Postmarketing surveillance study of Norplant in developing countries. | 2001 Jun 9 |
|
Clinical recommendations for oxcarbazepine. | 2001 Mar |
|
[Contraception with depot gestagens]. | 2001 May |
|
The effect of hormone replacement therapy on serum homocysteine levels in perimenopausal women: a randomized controlled trial. | 2001 Oct |
|
Effects of natural products and nutraceuticals on steroid hormone-regulated gene expression. | 2001 Oct |
|
Effects of the levonorgestrel-releasing intrauterine system on proliferation and apoptosis in the endometrium. | 2001 Oct |
|
[Low-dose oral contraception and bone density]. | 2001 Sep |
|
[Postcoital emergency contraception]. | 2001 Sep |
|
Estimation of hormone replacement therapy influence on serum galanin level in postmenopausal women. | 2001 Sep |
|
Levonorgestrel-releasing IUD and breast cancer. | 2001 Sep |
|
Determination of circular dichroism and ultraviolet spectral parameters of norgestimate- and other Delta(4)-3-ketosteroid oxime isomers via normal phase HPLC method. | 2001 Sep |
|
Validity of radioimmunological methods for determining free testosterone in serum. | 2001 Sep |
|
Endometrial expression of glycodelin in women with levonorgestrel-releasing subdermal implants. | 2001 Sep |
|
A randomized, controlled trial of a low-dose contraceptive containing 20 microg of ethinyl estradiol and 100 microg of levonorgestrel for acne treatment. | 2001 Sep |
|
Contraceptive dispensing and selection in school-based health centers. | 2001 Sep |
|
Assessment of the oestrogenic activity of the contraceptive progestin levonorgestrel and its non-phenolic metabolites. | 2001 Sep 14 |
|
Effect of hormone replacement therapy on lipids in perimenopausal and early postmenopausal women. | 2001 Sep 28 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/drp/norgestrel.html
OVRETTE tablets (0.075 mg norgestrel) are available in packages of 6 PILPAK dispensers with 28 tablets each as follows: NDC 0008-0062-01, yellow, round tablet marked "WYETH" on one side and "62" on reverse side. To achieve maximum contraceptive effectiveness, OVRETTE must be taken exactly as directed. One tablet is taken every day, at the same time. Administration is continuous, with no interruption between pill packs.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8494728
Norgestrel stimulated MCF-7 cell proliferation at a concentration of 10(-8) M.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:26:17 GMT 2025
by
admin
on
Mon Mar 31 18:26:17 GMT 2025
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Record UNII |
VF642934XZ
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C776
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C77014
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62954
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Levonorgestrel acetate
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VF642934XZ
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300000034879
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1471925
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DTXSID301314299
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