Levonorgestrel
From DrugPedia: A Wikipedia for Drug discovery
(New page: 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...) |
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| - | Levonorgestrel | + | '''Levonorgestrel''' 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. | ||
| - | KEGG(C08149,C08153,D00950,D00954) | + | '''KEGG'''(C08149,C08153,D00950,D00954) |
| - | Activity Progestin | + | '''Activity''' Progestin |
| - | + | {| border="1;width:100%; height:200px;style=text-align:center" | |
| - | Physical Property | + | |+'''Physiochemical properties of Levonorgestrel:''' |
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| + | ! style="background:brown; color:white" |Physical Property | ||
| + | ! style="background:brown; color:white" |Value | ||
| + | ! style="background:brown; color:white" |Units | ||
| + | ! style="background:brown; color:white" |Temp (deg C) | ||
| + | ! 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]] |
| - | + | [[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== | |
| - | + | {{Reflist}} | |
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| - | |- | + | ==External links== |
| - | + | * [http://www.levonelle.co.uk/ Levonelle] manufacturer's product information from [[Schering]] | |
| - | | | + | * [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]] |
| - | + | [[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
| 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:. 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:. PMID 16291771.</ref>
[edit] Usage
[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
[edit] External links
- Levonelle manufacturer's product information from Schering
- Monograph for levonorgestrel - Uk Medicines Information
