19-Norethindrone acetate

Chemical properties

White Solid

Originator

Norlestrin,Parke Davis ,US,1964

The Uses of 19-Norethindrone acetate

Progesteron. Norethindrone and acetate in combination with estrogen as contraceptive (oral). It is reasonably anticipated to be a human carcinogen.

The Uses of 19-Norethindrone acetate

Oral contraceptive (in combination with estrogen)

Definition

ChEBI: A 3-oxo Delta4-steroid that is norethisterone in which the hydroxy group has been converted to its acetate ester.

Manufacturing Process

2.98 grams of 17-ethinyl-19-nor-testosterone (norethindrone) are suspended in 30 cc of acetic anhydride and a solution of 1.9 grams of p-toluenesulfonic acid in 19 cc of acetic anhydride is gradually added while cooling and stirring. Complete dissolution takes place after about one hour. After additional 30 to 60 minutes, a thick, pasty mass separates. The reaction is permitted to continue for a total period of 5 hours, whereupon water is added to the reaction mixture and the 3-enol-17-diacetate which separates after stirring for 1 to 2 hours is filtered off, washed until neutral and dried in vacuo over calcium chloride at room temperature.
In order to prepare the monoacetate, the crude diacetate is suspended in 150 cc of methanol and, after adding 1.5 cc, concentrated hydrochloric acid, heated to boiling for 15 minutes in a nitrogen atmosphere. The crude monoacetate which separates upon the addition of water after cooling is filtered off, washed and dried in vacuo over calcium chloride at room temperature. The pure 17-acetete, obtained after repeated recrystallizations from methylene chloride/hexane has a MP of 161° to 162°C.

brand name

Aygestin (Duramed); Norlutate (Parke-Davis).

Therapeutic Function

Chemical Name: 19-Nor-17α-pregn-4-en-20-yn-3one, 17-hydroxy-, acetate

General Description

Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards

Safety Profile

Suspected carcinogen with experimental tumorigenic data. Human reproductive effects by ingestion and implant routes: menstrual cycle changes, postpartum effects, and changes in fertility. A human teratogen by an unspecified route with developmental abnormalities of the urogenital system. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. Used in the treatment of menstrual dsorders and uterine bleedmg.