Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H28O2 |
| Molecular Weight | 312.4458 |
| Optical Activity | ( + ) |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12CC[C@](O)(C#C)[C@]1(CC)CC[C@@]3([H])[C@]4([H])CCC(=O)C=C4CC[C@]23[H]
InChI
InChIKey=WWYNJERNGUHSAO-XHCJJCCMSA-N
InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m1/s1
Norgestrel,(+) (dextronorgestrel) is the biologically inactive isomer of norgestrel. Dextronorgestrel showed no ability to displace labelled levonorgestrel from the sex hormone binding globulin sites. In vitro active form being converted mainly to the 16 beta-hydroxysteroid and inactive form to the 16 alpha-hydroxysteroid. There was practically no binding to dextronorgestrel of dextronorgestrel to a cytoplasmic receptor prepared from the myometrium of estrogenized immature female rabbits was investigated. While some medications may contain dextronorgestrel, they are often labeled in terms of their levonorgestrel content only, ignoring the inert isomer.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Binding of the contraceptive steroids norgestrel and norethisterone in human plasma. | 1980 May |
|
| Relative binding affinity of various progestins and antiprogestins to a rabbit myometrium receptor. | 1989 Feb |
|
| [Capillary electrochromatography for chiral separation and purity testing of pharmaceutical drug substances]. | 2003 |
Patents
Sample Use Guides
Each incubation tube contained 12 mM NADPH, 0.1 ml nicotinamide solution, 0.1 ml 0.1 mM MgCl, solution, 0.1 ml 0.1 mM MnCl, solution and 4 ml rabbit microsomal suspension (equivalent to 40 mg protein). The radioactive steroid (5.4 u Ci in 0.05 ml propane-1,2-diol) was added to the tube and the volume made up to 6ml with 0.5 M Tris buffer pH 7.4. The steroid-tissue ratio was 1:400. The metabolism of D-norgestrel was rapid, more than 50% being metabolised within 10 min and more than 80% within 30 min, whereas for the biologically inactive L-norgestrel, only 50% had been metabolised after 30min incubation.
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SUBSTANCE RECORD
