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 | |
| Clinical data | |
| Trade names | Norplant |
| MedlinePlus | a610021 |
| Pregnancy cat. | X |
| Legal status | Rx-OTC |
| Routes | Implant; insert (extended-release); oral |
| Pharmacokinetic data | |
| Bioavailability | ~100% |
| Protein binding | 55% |
| Metabolism | Hepatic via CYP3A4 |
| Half-life | 36 ± 13 hours |
| Excretion | Renal: 45%; Fecal:32% |
| Identifiers | |
| CAS number |
797-63-7 
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| ATC code | G03AC03 G03AD01 |
| PubChem | CID 13109 |
| IUPHAR ligand | 2881 |
| DrugBank | DB00367 |
| ChemSpider |
12560
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| UNII |
5W7SIA7YZW
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| KEGG |
D00950
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| ChEBI |
CHEBI:6443
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| ChEMBL |
CHEMBL1389
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| Chemical data | |
| Formula | C21H28O2 |
| Mol. mass | 312.446 g/mol |
| SMILES | eMolecules & PubChem |
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Levonorgestrel (or l-norgestrel or D-norgestrel) (Plan B, Next Choice, and others[1]) is a second generation synthetic progestogen used as an active ingredient in some hormonal contraceptives, including combined oral contraceptive pills, progestogen only pills, emergency contraceptive pills, intrauterine systems and contraceptive implants.
Chemistry
Levonorgestrel (levo=left) is one form of a hormone that exists in two mirror image left and right forms.
Chemically, it is a hormonally active levorotatory enantiomer of the racemic mixture norgestrel. It is a gonane progestin derived from 19-nortestosterone.[2]
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.[3]
If taken together with drugs that induce the CYP3A4 cytochrome liver enzyme, the levonorgestrel will be metabolized faster and have lower efficacy, and a larger dose will be needed.[citation needed]
Usage
Oral contraception
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 1.5 mg (as a single dose or as two .75 mg doses 12 hours apart) taken within 3 days of unprotected sex, with one study indicating that beginning as late as 120 hours (5 days) after intercourse could be effective. There are many brand names of levonorgestrel-only ECPs, including: Escapelle, Plan B, Levonelle, NorLevo, Postinor-2, i-pill, "Next Choice" and 72-HOURS.[4]
Intrauterine system
Levonorgestrel is the active ingredient in the Mirena intrauterine system.
Contraceptive implants
Levonorgestrel is the active ingredient in Norplant and Jadelle.
Side effects
Possible side effects of levonorgestrel include nausea, vomiting, stomach pain, dizziness, breast tenderness, tiredness and weakness, headache, menstrual changes, and diarrhea.[5]
It decreases total and free testosterone, androstenedione, dehydroepiandrosterone sulfate (DHEAS), dihydrotestosterone (DHT) and sex hormone–binding globulin (SHBG), but has no effect on sexual function or markers of androgen bioactivity.[6]
References
- ^ http://ec.princeton.edu/questions/dose.html#dose
- ^ Edgren RA, Stanczyk FZ (1999). "Nomenclature of the gonane progestins". Contraception 60 (6): 313. doi:10.1016/S0010-7824(99)00101-8. PMID 10715364.
- ^ Sitruk-Ware R (2006). "New progestagens for contraceptive use". Hum Reprod Update 12 (2): 169–78. doi:10.1093/humupd/dmi046. PMID 16291771.
- ^ Trussell, James; Cleland, Kelly (2007-04-10). "Emergency Contraceptive Pills Worldwide". Princeton University. http://ec.princeton.edu/questions/dedicated.html. Retrieved 2007-05-28.
- ^ MedicineNet.com > LEVONORGESTREL - ORAL (lee-voh-nor-JEST-rell) Retrieved on April 3, 2010
- ^ Kovalevsky G, Ballagh SA, Stanczyk FZ, Lee J, Cooper J, Archer DF (April 2010). "Levonorgestrel effects on serum androgens, sex hormone-binding globulin levels, hair shaft diameter, and sexual function". Fertil. Steril. 93 (6): 1997–2003. doi:10.1016/j.fertnstert.2008.12.095. PMID 19394598.
External links
- Levonelle manufacturer's product information from Schering
- Monograph for levonorgestrel - Uk Medicines Information
- U.S. National Library of Medicine: Drug Information Portal - Levonorgestrel
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