Norgestrel

Norgestrel Basic information
Product Name:Norgestrel
Synonyms:dl-13b-ethyl-17a-ethynyl-17b-hydroxygon-4-en-3-one;4-GONEN-13BETA-ETHYL-17ALPHA-ETHYNYL-17BETA-OL-3-ONE;4-PREGNEN-13BETA-ETHYL-18,19-DINOR 17BETA-OL-3-ONE-20-YNE;4-ESTREN-17-ALPHA-ETHYNYL-18-HOMO-17-BETA-OL-3-ONE(+/-);D(-)-NORGESTREL;D-NORGESTREL;(+-)-13-ethyl-17-hydroxy-18,19-dinor-17-alpha-pregn-4-en-20-yn-3-one;13-ethyl-17-hydroxy-19-dinorpregn-4-en-20-yn-3-on(17-alpha)-(+-)-1
CAS:6533-00-2
MF:C21H28O2
MW:312.45
EINECS:229-433-5
Product Categories:Inhibitors;Metabolites & Impurities;Intermediates & Fine Chemicals;Chiral Reagents;Glucuronides;SARIDON;Hormone;Pharmaceuticals;Steroids
Mol File:6533-00-2.mol
Norgestrel Structure
Norgestrel Chemical Properties
Melting point 239-241 °C(lit.)
Boiling point 392.36°C (rough estimate)
density 1.0697 (rough estimate)
refractive index 1.4900 (estimate)
storage temp. 2-8°C
solubility Chloroform (Slightly, Sonicated), Dichloromethane (Slightly), Methanol (Slightly)
pka13.09±0.40(Predicted)
form neat
color Crystals from diethyl ether-hexane
InChIKeyWWYNJERNGUHSAO-XUDSTZEESA-N
CAS DataBase Reference6533-00-2(CAS DataBase Reference)
EPA Substance Registry SystemNorgestrel (6533-00-2)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-40
Safety Statements 22-36
WGK Germany 3
RTECS JF8259000
HS Code 2937230000
Hazardous Substances Data6533-00-2(Hazardous Substances Data)
ToxicityLD50 oral in rat: 5010mg/kg
MSDS Information
ProviderLanguage
Norgestrel English
SigmaAldrich English
Norgestrel Usage And Synthesis
DescriptionNorgestrel 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.
Chemical PropertiesWhite Solid
UsesProgestogen; oral contraceptive. The bioactive enantiomer is levorotatory
UsesA metabolite of Norgestrel.
UsesProtected D-(-)-Norgestrel
UsesA glucuronide metabolite of Levonorgestrel.
UsesAn intermediate to the glucuronide metabolite of Levonorgestrel.
UsesIt is an excellent progestational and ovulation inhibiting steroid. The bioactive enantiomer is levorotatory. Progestogen; oral contraceptive.
Usesanalgesic, antipyretic
DefinitionChEBI: 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 nameOvrette (Wyeth).
General DescriptionNorgestrel, (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 ProfileHuman 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
Norgestrel Preparation Products And Raw materials
Norethindrone NORGESTREL-2,2,4,6,6,10-D6,98 ATOM % D 6-KETO LEVONORGESTREL Ethanol Norgestrel Norgestrel-D5 (-)-NORGESTREL 98%,(-)-NORGESTREL 98 Ethylparaben Norgestrel (L-),D(minus)-norgestrel,L-NORGESTREL,LEVONORGESTREL (D-(-)-NORGESTREL) norgestrel acetate Ethyl acetate Ethyl vanillin norgestrel 17-cyclopentanecarboxylate Etonogestrel Ethyl acrylate levo-norgestrel-poly(3-hydroxybutyrate) D-(-)-Norgestrel Sulfate,D-(-)-Norgestrel-17-sulfate Ethyl 4'-hydroxy-3'-methoxycinnamate

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