Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H28O2 |
Molecular Weight | 312.4458 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]
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
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021225s031lbl.pdfhttps://www.drugbank.ca/drugs/DB09389 | https://www.drugs.com/drp/norgestrel.html | https://www.ncbi.nlm.nih.gov/pubmed/8136310Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25698840
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021225s031lbl.pdfhttps://www.drugbank.ca/drugs/DB09389 | https://www.drugs.com/drp/norgestrel.html | https://www.ncbi.nlm.nih.gov/pubmed/8136310
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25698840
Norgestrel is synthetic steroidal progestin that is used in combination with ethinyl estradiol for oral contraception. Norgestrel is composed of a racemic mixture of two stereoisomers, dextronorgestrel and levonorgestrel. However, only the levorotary enantiomer (levonorgestrel) is biologically active. Norgestrel (and more specifically the active stereoisomer levonorgestrel) binds to the progesterone and estrogen receptors within the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like levonorgestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge. Loss of the LH surge inhibits ovulation and thereby prevents pregnancy. Norgestrel in combination with ethinyl estradiol is indicated for the prevention of pregnancy in women who elect to use this product as a method of contraception.
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 |
|||
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 |
|||
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 |
---|---|---|---|---|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
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: Page: p.10 |
healthy, 16-45 n = 1714 Health Status: healthy Condition: Prevention of pregnancy Age Group: 16-45 Sex: F Population Size: 1714 Sources: Page: p.10 |
Disc. AE: Bleeding... AEs leading to discontinuation/dose reduction: Bleeding (1.5%) Sources: Page: p.10 |
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: Page: p.2 |
healthy, 27.3 ± 5.7 n = 1700 Health Status: healthy Condition: Prevention of pregnancy Age Group: 27.3 ± 5.7 Sex: F Population Size: 1700 Sources: Page: p.2 |
Disc. AE: Menstrual irregularity, Amenorrhea... AEs leading to discontinuation/dose reduction: Menstrual irregularity (0.7%) Sources: Page: p.2Amenorrhea (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 Co-administed with:: ethinyl estradiol, p.o(20 ug; q.d; 1 year) Sources: Page: p.507 |
healthy, 27.6±6.7 n = 323 Health Status: healthy Condition: Prevention of pregnancy Age Group: 27.6±6.7 Sex: F Population Size: 323 Sources: Page: p.507 |
Disc. AE: Metrorrhagia, Bleeding vaginal... AEs leading to discontinuation/dose reduction: Metrorrhagia (8.7%) Sources: Page: p.507Bleeding 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: Page: p.10 |
healthy, 16-45 n = 1714 Health Status: healthy Condition: Prevention of pregnancy Age Group: 16-45 Sex: F Population Size: 1714 Sources: Page: p.10 |
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: Page: p.2 |
healthy, 27.3 ± 5.7 n = 1700 Health Status: healthy Condition: Prevention of pregnancy Age Group: 27.3 ± 5.7 Sex: F Population Size: 1700 Sources: Page: p.2 |
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: Page: p.2 |
healthy, 27.3 ± 5.7 n = 1700 Health Status: healthy Condition: Prevention of pregnancy Age Group: 27.3 ± 5.7 Sex: F Population Size: 1700 Sources: Page: p.2 |
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 Co-administed with:: ethinyl estradiol, p.o(20 ug; q.d; 1 year) Sources: Page: p.507 |
healthy, 27.6±6.7 n = 323 Health Status: healthy Condition: Prevention of pregnancy Age Group: 27.6±6.7 Sex: F Population Size: 323 Sources: Page: p.507 |
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 Co-administed with:: ethinyl estradiol, p.o(20 ug; q.d; 1 year) Sources: Page: p.507 |
healthy, 27.6±6.7 n = 323 Health Status: healthy Condition: Prevention of pregnancy Age Group: 27.6±6.7 Sex: F Population Size: 323 Sources: Page: p.507 |
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 |
---|---|---|
Nomenclature of the gonane progestins. | 1999 Dec |
|
A lower dosage levonorgestrel and testosterone combination effectively suppresses spermatogenesis and circulating gonadotropin levels with fewer metabolic effects than higher dosage combinations. | 1999 May-Jun |
|
Superficial endometrial vascular fragility in Norplant users and in women with ovulatory dysfunctional uterine bleeding. | 2000 Jul |
|
Effects of two oral contraceptives on plasma levels of insulin-like growth factor I (IGF-I) and growth hormone (hGH). | 2000 Nov |
|
Desogestrel plus testosterone effectively suppresses spermatogenesis but also causes modest weight gain and high-density lipoprotein suppression. | 2000 Oct |
|
The effectiveness of the levonorgestrel-releasing intrauterine system in menorrhagia: a systematic review. | 2001 Jan |
|
Internet availability of contraceptives. | 2001 Jan |
|
Indigenous notions of the workings of the body: conflicts and dilemmas with Norplant use in rural Bangladesh. | 2001 Jan |
|
A progestin-releasing intrauterine device for long-term contraception. | 2001 Jan 22 |
|
Long-acting delivery microspheres of levo-norgestrol-poly(3-hydroxybutyrate): their preparation, characterization and contraceptive tests on mice. | 2001 Jan-Feb |
|
Use of Norplant implants in the immediate postpartum period among asymptomatic HIV-1-positive mothers. | 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 |
|
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 |
|
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 |
|
Hormonal and barrier methods of contraception, oncogenic human papillomaviruses, and cervical squamous intraepithelial lesion development. | 2001 Jun |
|
Clinical recommendations for oxcarbazepine. | 2001 Mar |
|
Preferential prescribing of type of combined oral contraceptive pill by general practitioners to teenagers with acne. | 2001 Mar |
|
Practices of prescribing oral contraceptives in Poland. | 2001 Mar |
|
Progestin regulation of galanin and prolactin gene expression in oestrogen-induced pituitary tumours. | 2001 Mar |
|
Levonorgestrel-releasing intrauterine devices. | 2001 Mar 10 |
|
Levonorgestrel-releasing intrauterine devices. | 2001 Mar 10 |
|
[Levonorgestrel releasing intrauterine spiral--contraception and therapeutic indications]. | 2001 Mar 15 |
|
[Contraception with depot gestagens]. | 2001 May |
|
Effects of postmenopausal hormone replacement therapy on lipid, lipoprotein, and apolipoprotein (a) concentrations: analysis of studies published from 1974-2000. | 2001 May |
|
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 |
|
Effect of hormone replacement therapy on lipids in perimenopausal and early postmenopausal women. | 2001 Sep 28 |
Sample Use Guides
Mirena contains 52 mg of levonorgestrel (LNG). Initially, LNG is released at a rate of approximately 20 mcg/day. This rate decreases progressively to half that value after 5 years. Mirena must be removed by the end of the fifth year and can be replaced at the time of removal with a new Mirena if continued contraceptive protection is desired.
Route of Administration:
Vaginal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26161412
5 × 10(-5) mol/L Levonorgestrel (LNG) revealed a time-dependent inhibition of cell proliferation and an increase of apoptosis in both human endometrial stromal cells (HESCs) and glandular cells (HEGCs). Furthermore, these cells demonstrated a significant Gap Junctional Intercellular Communication (GJIC) enhancement upon treatment with 5 × 10(-5) mol/L for 48 hours. The effects of LNG were most noticeable in HESCs rather than in HEGCs.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-VATC |
QG03FA10
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
||
|
WHO-VATC |
QG03FB01
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
||
|
WHO-VATC |
QG03AA06
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
||
|
NCI_THESAURUS |
C776
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
||
|
WHO-ATC |
G03FA10
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
||
|
WHO-ATC |
G03AA06
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
||
|
LIVERTOX |
699
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
||
|
WHO-ATC |
G03FB01
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
13109
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
m8063
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | Merck Index | ||
|
NORGESTREL
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
7630
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
1472000
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
SUB09371MIG
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
D009644
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
100000092602
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
2157
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
6533-00-2
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
C703
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
DB09389
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
3595
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
3J8Q1747Z2
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
3J8Q1747Z2
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
757251
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
CHEMBL2107797
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | |||
|
7518
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY | RxNorm | ||
|
229-433-5
Created by
admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
PARENT (METABOLITE ACTIVE)