Norgestrel is a synthetic progestin and a racemic mixture of dextronorgestrel and levonorgestrel , of which levonorgestrel is the biologically active component. In vivo, norgestrel administered via intrauterine device (IUD) prevents pregnancy in rats. Formulations containing nogestrel have been used as contraceptives.
It is an excellent progestational and ovulation inhibiting steroid. The bioactive enantiomer is levorotatory. Progestogen; oral contraceptive.
A metabolite of Norgestrel.
Progestogen; oral contraceptive. The bioactive enantiomer is levorotatory
An intermediate to the glucuronide metabolite of Levonorgestrel.
Protected D-(-)-Norgestrel
A glucuronide metabolite of Levonorgestrel.
ChEBI: Levonorgestrel is a 17beta-hydroxy steroid, a 3-oxo-Delta(4) steroid and a terminal acetylenic compound. It has a role as a contraceptive drug, a progestin, a synthetic oral contraceptive and a female contraceptive drug. It is functionally related to a norgestrel. It is an enantiomer of a dexonorgestrel.
Norgestrel, (17α)-(±)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one, and levonorgestrel, (17α)-(-)-13-ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one,have a C13 ethyl group instead of the C13 methyl but haveprogestational properties similar to those of norethindrone,with decreased androgenic effects. The ethyl group apparentlyprovides unfavorable steric interactions with the ARthat reduce the affinity compared with that with the PRs.Norgestrel is a racemic mixture, while levonorgestrel is thesingle active levorotatory enantiomer. Norgestrel is usedonly in oral contraceptives. Levonorgestrel is used in bothoral combination birth control products and polymeric implantsthat provide contraception for up to 5 years.
Human reproductive effects byingestion and implant: menstrual cycle changes ordisorders and female fertility index changes. Anexperimental teratogen. Experimental reproductiveeffects. Questionable carcinogen with experimentalneoplastigenic data. An o
[1] R C JONES R A E A C Singer. The biological activities of norgestrel and its enantiomers.[J]. International Journal of Fertility, 1979, 24 1: 39-43.
[2] M.S. R C J. The Effects of an Intrauterine Device Containing Norgestrel in the Rat[J]. Fertility and sterility, 1974, 25 9: Pages 767-771. DOI:
10.1016/s0015-0282(16)40631-x
