Levonorgestrel (oral)

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Levonorgestrel (oral)
Clinical data
Pregnancy; category	X;
Routes of; administration	Implant; insert (extended-release); oral
ATC code	G03AC03 (WHO) ;
Pharmacokinetic data
Bioavailability	~100%
Protein binding	55%
Metabolism	Hepatic
Elimination half-life	36 ± 13 hours
Excretion	Renal: 45%; Fecal:32%
Identifiers
	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;
CAS Number	797-63-7;
PubChem CID	13109;
DrugBank	APRD00754;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C21H28O2
Molar mass	312.446 g/mol

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

Chemistry

Chemically, it is a hormonally active levorotatory enantiomer of the racemic mixture norgestrel. It is a gonane progestin derived from 19-nortestosterone.^[1]

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.^[2]

Usage

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: Plan B, Levonelle, NorLevo, Postinor-2, and 72-HOURS.^[3]

IUD

Levonorgestrel is the active ingredient in Mirena.

Contraceptive implants

Levonorgestrel is the active ingredient in Norplant and Jadelle.

References

↑ Edgren RA, Stanczyk FZ (1999). "Nomenclature of the gonane progestins". Contraception. 60 (6): 313. PMID 10715364.
↑ Sitruk-Ware R (2006). "New progestagens for contraceptive use". Hum Reprod Update. 12 (2): 169–78. PMID 16291771.
↑ Trussell, James; Cleland, Kelly (2007-04-10). "Emergency Contraceptive Pills Worldwide". Princeton University. Retrieved 2007-05-28.

External links

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

Template:Sex hormones Template:SIB de:Levonorgestrel nl:Levonorgestrel

Template:WikiDoc Sources

[1] Edgren RA, Stanczyk FZ (1999). "Nomenclature of the gonane progestins". Contraception. 60 (6): 313. PMID 10715364.

[2] Sitruk-Ware R (2006). "New progestagens for contraceptive use". Hum Reprod Update. 12 (2): 169–78. PMID 16291771.

[ecp_worldwide-3] Trussell, James; Cleland, Kelly (2007-04-10). "Emergency Contraceptive Pills Worldwide". Princeton University. Retrieved 2007-05-28.

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