NORGESTERONE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H28O2
Molecular Weight	300.4351
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@@](O)(C=C)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])CC(=O)CC4

InChI

InChIKey=YPVUHOBTCWJYNQ-SLHNCBLASA-N

InChI=1S/C20H28O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h3,16-18,22H,1,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H28O2
Molecular Weight	300.4351
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.sciencedirect.com/science/article/pii/0039128X65901339?via%3Dihub | https://www.drugfuture.com/chemdata/norgesterone.html | https://www.ncbi.nlm.nih.gov/pubmed/5997085 | https://www.ncbi.nlm.nih.gov/pubmed/24383838

Norgesterone (norvinodrel, vinylestrenolone) is a progestin medication which was formerly used in birth control pills for women. The compound shows no androgenic and very little estrogenic activity; its progestational effect, as well as other properties, suggests its use as claudogenic agent. Norgesterone is an agonist of the progesterone receptor. It was used in combination with ethinylestradiol in birth control pills to prevent pregnancy.

Originator

Approval Year

PubMed

Title	Date	PubMed
[Clinical investigations of the progestational activity of vinylestrenolone].	1962 Apr	13883015
[ON TREATMENT OF ESSENTIAL DYSMENORRHEA WITH VINYLESTRENOLONE-ETHINYLESTRADIOL COMBINATION].	1964 Jan 15	14124188
A case of eosinophilic myositis associated with orbital myositis.	2002 Mar	24383838

Patents

Sample Use Guides

In Vivo Use Guide

Rabbits: (Clauberg test) 4 mg, administered subcutaneously. When given by gavage the steroids were suspended in a 1% solution of Tween 80; when administered subcutaneously they were dissolved in olive oil. Norvinodrel showed 2+ response in all of four rabbits each given a total dose of 20 mg. The antiovulatory activity was tested in female rabbits: in this test Norvinodrel at 10 mg orally administered is able to partially inhibit the ovulation (33,3%) in four rabbits.

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:33:05 GMT 2023` Edited by `admin` on `Fri Dec 15 16:33:05 GMT 2023`
Record UNII	YFS274763Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NORGESTERONE

Official Name

English

NORVINODREL

Common Name

English

norgesterone [INN]

Common Name

English

NSC-72160

Code

English

17.ALPHA.-VINYL-5(10)-ESTRENE-17.BETA.-OL-3-ONE

Common Name

English

VINYLESTRENOLONE

Common Name

English

17.BETA.-HYDROXY-17.ALPHA.-VINYLESTR-5(10)-EN-3-ONE

Systematic Name

English

(17.ALPHA.)-17-HYDROXY-19-NORPREGNA-5(10),20-DIEN-3-ONE

Common Name

English

NORGESTERONE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C776