17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether

Chemical properties

Crystalline Solid

Originator

Enovid ,Searle ,US ,1957

The Uses of 17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether

Mestranol is an orally active estrogenic steroid. It was the estrogen used in many of the first oral contraceptives

The Uses of 17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether

antiemetic

The Uses of 17a-Ethynyl-1,3,5(10)-estratriene-3,17b-diol 3-methyl ether

Pharmacological estrogen molecule

Background

The 3-methyl ether of ethinyl estradiol. It must be demethylated to be biologically active. It is used as the estrogen component of many combination ORAL contraceptives.

Indications

Mestranol was used as one of the first oral contraceptives.

What are the applications of Application

Mestranol is an orally active estrogenic steroid

Definition

ChEBI: A terminal acetylenic compound that is (17alpha)-17-ethynylestra-1(10),2,4-triene substituted by a methoxy group at position 3 and a hydroxy group at position 17.

Manufacturing Process

A stirred solution of 120 parts of 3-methoxy-δ1,3,5-estratrien-17-one in 2,600 parts of anhydrous toluene and 4,300 parts of anhydrous ether is saturated with a slow stream of acetylene. In the course of 30 minutes there is added a solution of 120 parts of potassium tert-amylate in 2,800 parts of anhydrous tert-pentanol. The passage of acetylene and stirring are continued for an additional 5 hours after which the reaction mixture is washed 5 times with 3,000-part portions of saturated ammonium chloride solution and then with water. It is then dried over anhydrous sodium sulfate and concentrated to dryness under vacuum. The residue is recrystallized from methanol. The 3- methoxy-17-ethynyl-δ1,3,5 estratrien-17-ol thus obtained melts at about 143° to 146°C. A further recrystallization from acetone yields crystals melting at about 150° to 151°C.

Therapeutic Function

Estrogen

Safety Profile

Confirmed carcinogen with experimental. neoplastigenic, tumorigenic, and teratogenic data. Moderately toxic by subcutaneous route. Human reproductive effects by ingestion: changes in ovaries and fallopian tubes, ferthty effects. Experimental reproductive effects. Mutation data reported. An FDA proprietary drug. A steroid used in oral contraceptives. When heated to decomposition it emits acrid smoke and irritating fumes.

Metabolism