Description
Norgestrel is a synthetic progestin and a racemic mixture of dextronorgestrel and levonorgestrel (Item No.
10006318), of which levonorgestrel is the biologically active component.
1 In vivo, norgestrel administered
via intrauterine device (IUD) prevents pregnancy in rats.
2 Formulations containing nogestrel have been used as contraceptives.
Chemical Properties
White Solid
Uses
A glucuronide metabolite of Levonorgestrel.
Uses
A metabolite of Norgestrel.
Uses
An intermediate to the glucuronide metabolite of Levonorgestrel.
Uses
analgesic, antipyretic
Uses
It is an excellent progestational and ovulation inhibiting steroid. The bioactive enantiomer is levorotatory. Progestogen; oral contraceptive.
Uses
Progestogen; oral contraceptive. The bioactive enantiomer is levorotatory
Uses
Protected D-(-)-Norgestrel
Definition
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.
Brand name
Ovrette (Wyeth).
General Description
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.
Safety Profile
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
References
[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
