Levonorgestrel

  • IUPAC: (-) - 17β -hydroxy -18 -methyl- 19-nor - 17α - pregn -4-en -20 -in- 3-one
  • (-) -13 -ethyl- 17 -hydroxy- 18 ,19- dinor - 17α - pregn -4-en -20 -in- 3-one
  • (-)- Norgestrel

G03AC03 G03AA07 G03AB03 G03DA06 G03FA11 G03FB09 G02BA04

Progestins

Attention

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Levonorgestrel is a synthetic progestin 2nd generation, which is used for hormonal birth control ( contraception).

Area of ​​application

Levonorgestrel has been brought to market in 1966 and belongs to the second generation of the synthetic progestins. It serves as an active ingredient in several hormonal contraceptives:

  • Contraceptive pill ( in combination with a Estrogenderivat )
  • Subdermal implant hormone
  • IUS (trade name Mirena )
  • Minipill
  • Morning-after pill (oral postcoital contraception)

Levonorgestrel is also used in hormone replacement therapy for symptoms during menopause.

Effect

The effect of levonorgestrel is dependent on the dose and the time of ingestion in relation to the female menstrual cycle. In the context of contraception (as part of the contraceptive pill, the mini pill or Langzeitkontrazeptiva as the IUS ) inhibits the release of levonorgestrel called gonadotropic hormones from the pituitary gland. The gonadotropic hormones LH and FSH control the activity of the ovaries and remodeling processes in the endometrium.

Further, by the viscous effect of levonorgestrel the secretion of the cervix. This means that sperm only very isolated or can not reach the uterus. Other effects of levonorgestrel concern Tubenmotilität the fallopian tubes.

The exact effect of levonorgestrel emergency contraception in the context of ( morning after pill ) is unclear. Discussed are the inhibition of ovulation, an inhibitory effect on the transport of the ovum or sperm in the fallopian tubes as well as a disturbance in the implantation of the fertilized ovum.

Prescription

The morning-after pill and was always available on prescription in Germany. Although the competent committee of the Federal Institute for Drugs and Medical Devices ( BfArM) in 2004 advocated to dismiss the " morning after pill " on the basis of the hormone levonorgestrel from the prescription requirement, the levy system has not been changed.

Pro familia launched in May 2012, the campaign " Breakdown by 6" with the aim, then to make pill ' prescription.

In an open letter written in November 2012, the Professional Association of Gynaecologists ( BVF ) and the German Society of Gynecology and Obstetrics ( DGGG ) clearly speak out against the non-prescription of Levonorgestrel.

Production

A multi-step enantioselective synthesis of levonorgestrel is - described in the literature - starting from 6 -methoxy -1-tetralone.

CAS registry number PubChem Anatomical Therapeutic Chemical Classification System DrugBank Dangerous Substances Directive (67/548/EEC) Progestogen IUD with progestogen Hormone replacement therapy (menopause) Follicle-stimulating hormone Enantioselectivity Digital Object Identifier
249940
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