Levonorgestrel

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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]].	+	'''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
		+	{| border="1;width:100%; height:200px;style=text-align:center"
		+	|+'''Physiochemical properties of Levonorgestrel:'''
		+	|-
		+	! 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
		+	|-
		+	|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
		+	|-
		+	|}
	==Chemistry==		==Chemistry==
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	{{pharma-stub}}		{{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
-	{| border="1;width:100%; height:200px;style=text-align:center"
-	|+'''Physiochemical properties of Estradiol:'''
-	|-
-	! 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
-	|-
-	|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
-	|-
-	|}

---

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 1 Chemistry 2 Usage 2.1 Oral contraceptives 2.2 Emergency contraception 2.3 IUD 2.4 Contraceptive implants 3 References 4 External links

[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

[edit] External links

• Levonelle manufacturer's product information from Schering
• Monograph for levonorgestrel - Uk Medicines Information

Template:Sex hormonesTemplate:Pharma-stub