| Identification | More | [Name]
Norgestrel | [CAS]
6533-00-2 | [Synonyms]
13BETA-ETHYL-17ALPHA-ETHYNYL-17BETA-HYDROXYGON-4-EN-3-ONE
(+/-)-13-ETHYL-17ALPHA-HYDROXY-18,19-DINORPREGN-4-EN-20-YN-3-ONE
17-ALPHA-ETHYNYL-18-HOMO-19-NORTESTOSTERONE
18,19-DINOR-13-BETA-ETHYL-17-BETA-HYDROXY-4-PREGNEN-20-YN-3-ONE
18,19-DINOR-4-PREGNEN-20-YN-3-ONE
4-ESTREN-17-ALPHA-ETHYNYL-18-HOMO-17-BETA-OL-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
d(-)-13beta-ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one
dl-13b-ethyl-17a-ethynyl-17b-hydroxygon-4-en-3-one
D(-)-NORGESTREL
D-NORGESTREL
LEVONORGESTREL
NORGESTREL
NORGESTREL(LEVO)
NORPLANT
OVRETTE(R)
(+-)-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
alpha-norgestrel | [EINECS(EC#)]
212-349-8 | [Molecular Formula]
C21H28O2 | [MDL Number]
MFCD01546387 | [Molecular Weight]
312.45 | [MOL File]
6533-00-2.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [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) | [form ]
neat | [pka]
13.09±0.40(Predicted) | [color ]
Crystals from diethyl ether-hexane | [Usage]
Progestogen; oral contraceptive. The bioactive enantiomer is levorotatory | [InChIKey]
WWYNJERNGUHSAO-XUDSTZEESA-N | [CAS DataBase Reference]
6533-00-2(CAS DataBase Reference) | [EPA Substance Registry System]
6533-00-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S22:Do not breathe dust .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [RTECS ]
JF8259000
| [HS Code ]
2937230000 | [Hazardous Substances Data]
6533-00-2(Hazardous Substances Data) | [Toxicity]
LD50 oral in rat: 5010mg/kg |
| Hazard Information | Back Directory | [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 | [storage]
Store at RT |
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