Levonorgestrel

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{{drugbox
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| 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
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| image = Levonorgestrel.svg
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| image2 = Levonorgestrel3d.png
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| width2 = 200
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| CAS_number = 797-63-7
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| ATC_prefix = G03
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| ATC_suffix = AC03
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| ATC_supplemental =
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| PubChem = 13109
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| DrugBank = APRD00754
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| C = 21 | H = 28 | O = 2
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| molecular_weight = 312.446 g/mol
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| bioavailability = ~100%
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| protein_bound = 55%
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| metabolism = [[Liver|Hepatic]]
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| elimination_half-life = 36 ± 13 hours
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| excretion = [[Kidney|Renal]]: 45%; [[Feces|Fecal]]:32%
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| pregnancy_US = <!-- A / B / C / D / X -->
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| pregnancy_category = X
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| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
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| legal_UK = <!-- GSL / P / POM / CD -->
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| legal_US = <!-- OTC / Rx-only -->
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| legal_status =
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| routes_of_administration = [[Implant (medicine)|Implant]]; insert (extended-release); oral
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}}
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'''Levonorgestrel''' (or''' ''[[Chirality (chemistry)#By optical activity: (+)- and (−)-|l]]''-[[norgestrel]]''' or '''<small>[[Chirality (chemistry)#By configuration: D- and L-|D]]</small>-[[norgestrel]]''') is a synthetic [[progestagen|progestogen]] used as an active ingredient in some [[Hormonal contraception|hormonal contraceptives]].
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==Chemistry==
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Chemically, it is a [[steroid hormone|hormonally]] active [[levorotatory]] [[enantiomer]] of the [[racemic mixture]] [[norgestrel]]. It is a gonane [[progestin]] derived from 19-[[nortestosterone]].<ref>{{cite journal |author=Edgren RA, Stanczyk FZ |year=1999 |title=Nomenclature of the gonane progestins |journal=Contraception |volume=60 |issue=6 |pages=313 |pmid=10715364 |doi=10.1016/S0010-7824(99)00101-8}}</ref>
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Its ''[[in vitro]]'' relative [[ligand (biochemistry) | binding affinities]] at human [[steroid hormone receptor]]s 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]].<ref>{{cite journal |author=Sitruk-Ware R |year=2006 |title=New progestagens for contraceptive use |journal=Hum Reprod Update |volume=12 |issue=2 |pages=169–78 |pmid=16291771 |doi=10.1093/humupd/dmi046}}</ref>
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==Usage==
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{{main|birth control}}
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===Oral contraceptives===
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At low doses, levonorgestrel is used in [[Oral contraceptive formulations|monophasic]] and [[Oral contraceptive formulations|triphasic]] formulations of [[combined oral contraceptive pill]]s, with available monophasic doses ranging from 100-250 µg, and triphasic doses of 50 µg/75 µg/125 µg.
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At very low daily dose of 30 µg, levonorgestrel is used in some [[progestogen only pill]]
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[[Oral contraceptive formulations#Progestogen only pills|formulations]].
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===Emergency contraception===
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Levonorgestrel is used in [[Emergency_contraceptive_pill#Emergency_contraceptive_pills_.28ECPs.29|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: ''Escapelle'', ''Plan B'', ''Levonelle'', ''NorLevo'', ''Postinor-2'', and ''72-HOURS''.<ref name="ecp worldwide">{{cite web |author=Trussell, James; Cleland, Kelly |date=2007-04-10 |title=Emergency Contraceptive Pills Worldwide |url=http://ec.princeton.edu/questions/dedicated.html |publisher=[[Princeton University]] |accessdate=2007-05-28}}</ref>
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===[[Intrauterine device|IUD]]===
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Levonorgestrel is the active ingredient in [[Mirena]].
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===Contraceptive implants===
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Levonorgestrel is the active ingredient in [[Norplant]] and [[Norplant|Jadelle]].
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==References==
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{{Reflist}}
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==External links==
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* [http://www.levonelle.co.uk/ Levonelle] manufacturer's product information from [[Schering]]
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* [http://www.ukmi.nhs.uk/NewMaterial/html/docs/levonorg.pdf Monograph for levonorgestrel] - Uk Medicines Information
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{{Sex hormones}}
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[[Category:Hormonal contraception]]
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[[Category:Progestagens]]
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{{pharma-stub}}
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Levonorgestrel  
Levonorgestrel  
Pubchem(13109)
Pubchem(13109)

Revision as of 07:21, 30 October 2008

Image:Levonorgestrel.svg
Image:Levonorgestrel3d.png
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
Identifiers
CAS number 797-63-7
ATC code G03AC03
PubChem 13109
DrugBank APRD00754
Chemical data
Formula Template:OrganicBox atomTemplate:OrganicBox atomTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBox atomTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBoxTemplate:OrganicBox 
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

Levonorgestrel (or l-norgestrel or D-norgestrel) is a synthetic progestogen used as an active ingredient in some hormonal contraceptives.

Contents

Chemistry

Chemically, it is a hormonally active levorotatory enantiomer of the racemic mixture norgestrel. It is a gonane progestin derived from 19-nortestosterone.<ref>Edgren RA, Stanczyk FZ (1999). "Nomenclature of the gonane progestins". Contraception 60 (6): 313. doi:10.1016/S0010-7824(99)00101-8. PMID 10715364. </ref>

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.<ref>Sitruk-Ware R (2006). "New progestagens for contraceptive use". Hum Reprod Update 12 (2): 169–78. doi:10.1093/humupd/dmi046. PMID 16291771. </ref>

Usage

Main article: birth control

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: Escapelle, Plan B, Levonelle, NorLevo, Postinor-2, and 72-HOURS.<ref name="ecp worldwide">Template:Cite web</ref>

IUD

Levonorgestrel is the active ingredient in Mirena.

Contraceptive implants

Levonorgestrel is the active ingredient in Norplant and Jadelle.

References

Unknown extension tag "references"

External links

Template:Sex hormonesTemplate:Pharma-stub

Levonorgestrel Pubchem(13109)

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.

KEGG(C08149,C08153,D00950,D00954)

Activity Progestin

Physiochemical properties of Estradiol:
Physical Property Value Units Temp (deg C) Source
Melting Point 240 deg C EXP
Water Solubility 2.050 mg/L 25 EST
Vapor Pressure 3.93E-10 mm Hg 25 EST
Henry's Law Constant 7.70E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.14E-11 cm3/molecule-sec 25 EST
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