Product Name

Levonorgestrel

CAS Number

797-63-7

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Product Name:
Levonorgestrel
CAS Number:
797-63-7
Indication:
For the treatment of menopausal and postmenopausal disorders and alone or in combination with other hormones as an oral contraceptive.
Mode of Action:

Binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like levonorgestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.

Pharmacodynamics:

Levonorgestrel is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Levonorgestrel tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries.

Metabolism:

Hepatic

Toxicity:

LD50 >5000 mg/kg (orally in rats)

IUPAC:
(1S, 2R, 10R, 11S, 14R, 15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0, {2, 7}.0, {11, 15}]heptadec-6-en-5-one
ATC:
G03AC03 G03AD01
PubChem:
13109
DrugBank:
DB00367 (APRD00106, APRD00754, DB00506)
Formula:
C29H33ClN2O2
Molecular Mass:
312.4458
Synonyms:
18-Methylnorethisterone d(-)-Norgestrel Levonorgestrelum [INN-Latin]
SMILES:
CC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1CC[C@@]2(O)C#C
AHFS Code:
08:12.0
InChi:
WWYNJERNGUHSAO-XUDSTZEESA-N
General Reference:
General Reference:

  1. Edgren RA, Stanczyk FZ: Nomenclature of the gonane progestins. Contraception. 1999 Dec;60(6):313. Pubmed
  2. Sitruk-Ware R: New progestagens for contraceptive use. Hum Reprod Update. 2006 Mar-Apr;12(2):169-78. Epub 2005 Nov 16. Pubmed

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