Levonorgestrel

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Levonorgestrel  
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'''Levonorgestrel''' Pubchem(13109)
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Pubchem(13109)
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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.
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.
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KEGG(C08149,C08153,D00950,D00954)
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'''KEGG'''(C08149,C08153,D00950,D00954)
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Activity Progestin
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'''Activity''' Progestin
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{| border="1;width:100%; height:200px;style=text-align:center"
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Physical Property Value Units Temp (deg C) Source
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|+'''Physiochemical properties of Levonorgestrel:'''
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! style="background:brown; color:white" |Physical Property
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! style="background:brown; color:white" |Value
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! style="background:brown; color:white" |Units  
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! style="background:brown; color:white" |Temp (deg C)
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! style="background:brown; color:white" |Source
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|Melting Point
|Melting Point
|240
|240
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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}}

Current revision

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 Levonorgestrel:
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

Contents

[edit] 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>

[edit] Usage

Main article: birth control

[edit] 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.

[edit] 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>

[edit] IUD

Levonorgestrel is the active ingredient in Mirena.

[edit] Contraceptive implants

Levonorgestrel is the active ingredient in Norplant and Jadelle.

[edit] References

Unknown extension tag "references"

[edit] External links

Template:Sex hormonesTemplate:Pharma-stub

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