DEXTRONORGESTREL

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

Structure Search

SMILES

CC[C@@]12CC[C@@H]3[C@H](CCC4=CC(=O)CC[C@@H]34)[C@H]1CC[C@]2(O)C#C

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

HIDE SMILES / InChI

Molecular Formula	C21H28O2
Molecular Weight	312.4458
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2730687 | https://www.ncbi.nlm.nih.gov/pubmed/6771468 | https://www.ncbi.nlm.nih.gov/pubmed/6887923

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

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
[Capillary electrochromatography for chiral separation and purity testing of pharmaceutical drug substances].	2003	12891896
Quantitative approach for the screening of cyclodextrins by nuclear magnetic resonance spectroscopy in support of chiral separations in liquid chromatography and capillary electrophoresis enantioseparation of norgestrel with alpha-, beta- and gamma-cyclodextrins.	2002-07-05	12184623
Relative binding affinity of various progestins and antiprogestins to a rabbit myometrium receptor.	1989-02	2730687
In vitro hydroxylation of the synthetic gestagen, norgestrel.	1983-08	6887923
Binding of the contraceptive steroids norgestrel and norethisterone in human plasma.	1980-05	6771468
The presence of dl-, d- and l-norgestrel and their metabolites in the plasma of women.	1975-09	1164851
Metabolism of D- and L-norgestrel in humans.	1975-06	169856
Excretion and stereoselective biotransformations of dl-, d- and l-norgestrel in women.	1975-05-01	238817

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:22:47 GMT 2025` Edited by `admin` on `Mon Mar 31 21:22:47 GMT 2025`
Record UNII	Z2QG2679YT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NORGESTREL (+)-FORM

Preferred Name

English

DEXTRONORGESTREL

Common Name

English

NORGESTREL, (+)-

Common Name

English

NORGESTREL (+)-FORM [MI]

Common Name

English

(8.ALPHA.,9.BETA.,10.ALPHA.,13.ALPHA.,14.BETA.)-13-ETHYL-17-HYDROXY-18,19-DINORPREGN-4-EN-20-YN-3-ONE

Common Name

English

Code System Code Type Description

FDA UNII

Z2QG2679YT