Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H28O2 |
Molecular Weight | 312.4458 |
Optical Activity | ( - ) |
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(O)C#C
InChI
InChIKey=WWYNJERNGUHSAO-XUDSTZEESA-N
InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
Molecular Formula | C21H28O2 |
Molecular Weight | 312.4458 |
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 |
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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 |
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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 |
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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 |
---|---|---|
Post-marketing surveillance of Norplant contraceptive implants: I. Contraceptive efficacy and reproductive health. | 2001 Apr |
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Rat uterine complement C3 expression as a model for progesterone receptor modulators: characterization of the new progestin trimegestone. | 2001 Aug |
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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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What is the risk of venous thromboembolism (VTE) among women taking third-generation oral contraceptives (OCs) in comparison with those taking contraceptives containing levonorgestrel? | 2001 Feb |
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Contraceptive use at the family planning clinic of the University of Nigeria Teaching Hospital, Enugu, Nigeria. | 2001 Jan |
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Sixty thousand woman-years of experience on the levonorgestrel intrauterine system: an epidemiological survey in Finland. | 2001 Jan |
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Effects of oral contraceptives on breast epithelial proliferation. | 2001 Jan |
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Comparison of the lipoprotein, carbohydrate, and hemostatic effects of phasic oral contraceptives containing desogestrel or levonorgestrel. | 2001 Jan |
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Quality of life and cost-effectiveness of levonorgestrel-releasing intrauterine system versus hysterectomy for treatment of menorrhagia: a randomised trial. | 2001 Jan 27 |
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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 |
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Norgestimate. From the laboratory to three clinical indications. | 2001 Jul |
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A village would be nice but...it takes a long-acting contraceptive to prevent repeat adolescent pregnancies. | 2001 Jul |
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The development and regression of deciduosarcomas and other lesions caused by estrogens and progestins in rabbits. | 2001 Jul-Aug |
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Weight change and adverse event incidence with a low-dose oral contraceptive: two randomized, placebo-controlled trials. | 2001 Jun |
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Comparison of a novel norgestimate/ethinyl estradiol oral contraceptive (Ortho Tri-Cyclen Lo) with the oral contraceptive Loestrin Fe 1/20. | 2001 Jun |
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Treatment of menorrhagia with a novel 'frameless' intrauterine levonorgestrel-releasing drug delivery system: a pilot study. | 2001 Jun |
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Co-localization of matrix metalloproteinase-1 and mast cell tryptase in the human uterus. | 2001 Jun |
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Treatment of menorrhagia. | 2001 Jun 9 |
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Postmarketing surveillance study of Norplant in developing countries. | 2001 Jun 9 |
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Clinical recommendations for oxcarbazepine. | 2001 Mar |
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Implanon contraceptive implants: effects on carbohydrate metabolism. | 2001 Mar |
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The effects of peri-ovulatory administration of levonorgestrel on the menstrual cycle. | 2001 Mar |
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Preferential prescribing of type of combined oral contraceptive pill by general practitioners to teenagers with acne. | 2001 Mar |
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New IUD approved. | 2001 Mar |
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Use of a levonorgestrel-releasing intrauterine device in the treatment of rectovaginal endometriosis. | 2001 Mar |
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Contraception in the adolescent: an update. | 2001 Mar |
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Constant estrogen, intermittent progestogen vs. continuous combined hormone replacement therapy: tolerability and effect on vasomotor symptoms. | 2001 Mar |
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Norplant and other implantable contraceptives. | 2001 Mar |
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Levonorgestrel-releasing intrauterine devices. | 2001 Mar 10 |
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[Low-dose oral contraception and bone density]. | 2001 Sep |
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Levonorgestrel-releasing IUD and breast cancer. | 2001 Sep |
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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 |
|
Contraceptive dispensing and selection in school-based health centers. | 2001 Sep |
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
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Record UNII |
5W7SIA7YZW
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-ATC |
G03AC03
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WHO-VATC |
QG03AC03
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NDF-RT |
N0000011301
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WHO-VATC |
QG03AA07
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WHO-ESSENTIAL MEDICINES LIST |
18.3.1 (ETH/LEV)
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WHO-VATC |
QG03AB03
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WHO-ATC |
G03AA07
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WHO-ATC |
G03AD01
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WHO-ATC |
G03FB09
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NCI_THESAURUS |
C776
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NDF-RT |
N0000175830
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LIVERTOX |
555
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WHO-ATC |
G03FA11
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NDF-RT |
N0000175602
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NDF-RT |
N0000175832
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WHO-VATC |
QG03AD01
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WHO-VATC |
QG03FB09
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WHO-VATC |
QG03FA11
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WHO-ESSENTIAL MEDICINES LIST |
18.3.1
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WHO-ATC |
G03AB03
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Code System | Code | Type | Description | ||
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DTXSID3036496
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1362602
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5W7SIA7YZW
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Intrauterine Levonorgestrel
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3475
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SUB08483MIG
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13109
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D016912
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212-349-8
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744007
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Oral Levonorgestrel
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m8063
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PRIMARY | Merck Index | ||
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LEVONORGESTREL
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PRIMARY | Description: A white or almost white, crystalline powder; odourless. Solubility: Practically insoluble in water; slightly soluble in ethanol (~750 g/l) TS and ether R. Category: Contraceptive. Storage: Levonorgestrel should be kept in a well-closed container, protected from light.Definition: Levonorgestrel contains not less than 98.0% and not more than 102.0% of C21H28O2, calculated with reference to the dried substance. | ||
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CHEMBL1389
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PRIMARY | |||
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Levonorgestrel Implant
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5W7SIA7YZW
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1572
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DB00367
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6443
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100000091059
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797-63-7
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6483
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6373
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2881
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LEVONORGESTREL
Created by
admin on Mon Mar 31 17:54:06 GMT 2025 , Edited by admin on Mon Mar 31 17:54:06 GMT 2025
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C47585
Created by
admin on Mon Mar 31 17:54:06 GMT 2025 , Edited by admin on Mon Mar 31 17:54:06 GMT 2025
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Related Record | Type | Details | ||
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ENANTIOMER -> ENANTIOMER |
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RACEMATE -> ENANTIOMER |
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
PLASMA; URINE
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PARENT -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
impurity O at 200 nm: maximum 0.3 per cent
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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