Levonorgestrel
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| Levonorgestrel
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| Systematic (IUPAC) name | |
| 13-ethyl-17-ethynyl-17-hydroxy- 1,2,6,7,8,9,10,11,12,13,14,15,16, 17- tetradecahydrocyclopenta[a] phenanthren-3-one | |
| Identifiers | |
| CAS number | |
| ATC code | G03 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C21H28O2 |
| Mol. mass | 312.446 g/mol |
| Pharmacokinetic data | |
| Bioavailability | ~100% |
| Protein binding | 55% |
| Metabolism | Hepatic |
| Half life | 36 ± 13 hours |
| Excretion | Renal: 45%; Fecal:32% |
| Therapeutic considerations | |
| Pregnancy cat. |
X |
| Legal status | |
| Routes | Implant; insert (extended-release); oral |
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Levonorgestrel (or l-norgestrel or D-norgestrel) is a synthetic progestogen used as an active ingredient in some hormonal contraceptives.
Chemistry
Chemically, it is a hormonally active levorotatory enantiomer of the racemic mixture norgestrel. It is a gonane progestin derived from 19-nortestosterone.[1]
Its in vitro relative binding affinities at human steroid hormone receptors are: 323% that of progesterone at the progesterone receptor, 58% that of testosterone at the androgen receptor, 17% that of aldosterone at the mineralocorticoid receptor, 7.5% that of cortisol at the glucocorticoid receptor, and <0.02% that of estradiol at the estrogen receptor.[2]
Usage
Oral contraceptives
At low doses, levonorgestrel is used in monophasic and triphasic formulations of combined oral contraceptive pills, with available monophasic doses ranging from 100-250 µg, and triphasic doses of 50 µg/75 µg/125 µg.
At very low daily dose of 30 µg, levonorgestrel is used in some progestogen only pill formulations.
Emergency contraception
Levonorgestrel is used in emergency contraceptive pills (ECPs), both in a combined Yuzpe regimen which includes estrogen, and as a levonorgestrel-only method. The levonorgestrel-only method uses levonorgestrel 1500 μg (as a single dose or as two 750 μg doses 12 hours apart) taken within 3 days of unprotected sex. There are many brand names of levonorgestrel-only ECPs, including: Plan B, Levonelle, NorLevo, Postinor-2, and 72-HOURS.[3]
IUD
Levonorgestrel is the active ingredient in Mirena.
Contraceptive implants
Levonorgestrel is the active ingredient in Norplant and Jadelle.
References
- ↑ Edgren RA, Stanczyk FZ (1999). "Nomenclature of the gonane progestins". Contraception 60 (6): 313. PMID 10715364.
- ↑ Sitruk-Ware R (2006). "New progestagens for contraceptive use". Hum Reprod Update 12 (2): 169-78. PMID 16291771.
- ↑ Trussell, James; Cleland, Kelly (2007-04-10). Emergency Contraceptive Pills Worldwide. Princeton University. Retrieved on 2007-05-28.
External links
- Levonelle manufacturer's product information from Schering
- Monograph for levonorgestrel - Uk Medicines Information
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
