Levonorgestrel

Levonorgestrel
Levonorgestrel

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 MedlinePlus Pregnancy cat. Legal status Routes Norplant a610021 X Rx-OTC Implant; insert (extended-release); oral Pharmacokinetic data Bioavailability Protein binding Metabolism Half-life Excretion ~100% 55% Hepatic via CYP3A4 36 13 hours Renal: 45%; Fecal:32% Identifiers CAS number ATC code PubChem IUPHAR ligand DrugBank ChemSpider UNII 797-63-7 [2] G03AD01 [4] [1]

G03AC03

[3]

CID 13109 2881 [6]

[5]

DB00367 12560 [8]

[7] [9]

5W7SIA7YZW

Levonorgestrel
[10]

2
KEGG ChEBI ChEMBL

D00950

[11]

CHEBI:6443

CHEMBL1389 Chemical data

[12]

Formula Mol. mass

C21H28O2 312.446 g/mol

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[13]

Levonorgestrel (or l-norgestrel or D-norgestrel) (Plan B, Next Choice, and others[14]) 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.[15] 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.[16] 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.

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 g, and triphasic doses of 50 g/75 g/125 g. At very low daily dose of 30 g, 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, Glanique, NorLevo, Postinor-2, i-pill, "Next Choice" and 72-HOURS.[17]

Levonorgestrel

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.[18] It decreases total and free testosterone, androstenedione, dehydroepiandrosterone sulfate (DHEAS), dihydrotestosterone (DHT) and sex hormonebinding globulin (SHBG), but has no effect on sexual function or markers of androgen bioactivity.[19]

References
[1] http:/ / www. nlm. nih. gov/ medlineplus/ druginfo/ meds/ a610021. html [2] http:/ / www. nlm. nih. gov/ cgi/ mesh/ 2009/ MB_cgi?term=797-63-7& rn=1 [3] http:/ / www. whocc. no/ atc_ddd_index/ ?code=G03AC03 [4] http:/ / www. whocc. no/ atc_ddd_index/ ?code=G03AD01 [5] http:/ / pubchem. ncbi. nlm. nih. gov/ summary/ summary. cgi?cid=13109 [6] http:/ / www. iuphar-db. org/ DATABASE/ LigandDisplayForward?ligandId=2881 [7] http:/ / www. drugbank. ca/ drugs/ DB00367 [8] http:/ / www. chemspider. com/ Chemical-Structure. 12560 [9] http:/ / fdasis. nlm. nih. gov/ srs/ srsdirect. jsp?regno=5W7SIA7YZW [10] http:/ / www. kegg. jp/ entry/ D00950 [11] https:/ / www. ebi. ac. uk/ chebi/ searchId. do?chebiId=CHEBI:6443 [12] https:/ / www. ebi. ac. uk/ chembldb/ index. php/ compound/ inspect/ CHEMBL1389 [13] http:/ / en. wikipedia. org/ wiki/ Special%3Acomparepages?rev1=462091161& page2=%3ALevonorgestrel [14] http:/ / ec. princeton. edu/ questions/ dose. html#dose [15] Edgren RA, Stanczyk FZ (1999). "Nomenclature of the gonane progestins". Contraception 60 (6): 313. doi:10.1016/S0010-7824(99)00101-8. PMID10715364. [16] Sitruk-Ware R (2006). "New progestagens for contraceptive use". Hum Reprod Update 12 (2): 16978. doi:10.1093/humupd/dmi046. PMID16291771. [17] Trussell, James; Cleland, Kelly (2007-04-10). "Emergency Contraceptive Pills Worldwide" (http:/ / ec. princeton. edu/ questions/ dedicated. html). Princeton University. . Retrieved 2007-05-28. [18] MedicineNet.com > LEVONORGESTREL - ORAL (lee-voh-nor-JEST-rell) (http:/ / www. medicinenet. com/ levonorgestrel-oral/ article. htm) Retrieved on April 3, 2010 [19] 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): 19972003. doi:10.1016/j.fertnstert.2008.12.095. PMID19394598.

External links
Levonelle (http://www.levonelle.co.uk/) manufacturer's product information from Schering Monograph for levonorgestrel (http://www.ukmi.nhs.uk/NewMaterial/html/docs/levonorg.pdf) - Uk Medicines Information U.S. National Library of Medicine: Drug Information Portal - Levonorgestrel (http://druginfo.nlm.nih.gov/ drugportal/dpdirect.jsp?name=Levonorgestrel)

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Levonorgestrel Source: http://en.wikipedia.org/w/index.php?oldid=502069779 Contributors: Alison, Andrew c, Anypodetos, Arcadian, Astragal, Beetstra, Casforty, Ceccomaster, Cindery, Clicketyclack, Col.Kiwi, El3ctr0nika, Everyking, Fvasconcellos, Ginkgo100, Goodmaker, HEL, HazyM, J.delanoy, Jiwhit01, Jkister, Kiral, Kristy21au, Louisajb, Lyrl, Mikael Hggstrm, MindZiper, Nbauman, Nick, Pashihiko, Peryeat, Radagast, Rest, Sas108, Schi, Sole Soul, Speciate, Tal Celes, 94 , anonymous edits

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