Etynodiol

Etynodiol
Ethynodiol_diacetate_synthesis.svg
INN
Drug class
Routes of administration
Pregnancy category
Bioavailability
Metabolism
Elimination half-life
Excretion
Legal status
CAS Number
PubChem
DrugBank
ChemSpider
KEGG

Ethynodiol is a synthetic progestogen, a type of medication that is used in hormonal contraceptives. It is a derivative of norethisterone and is used in combination with estrogens in oral contraceptive pills.

Chemical Structure

Chemical synthesis of Ethynodiol diacetate

Ethynodiol is chemically known as 19-norpregn-4-en-20-yne-3,17-diol. It is a derivative of norethisterone, which is a synthetic form of the hormone progesterone. The structure of ethynodiol includes an ethynyl group at the 17-alpha position, which is characteristic of many synthetic progestogens.

Pharmacology

Ethynodiol acts primarily as a progestogen, meaning it mimics the effects of the natural hormone progesterone. It works by altering the endometrium and cervical mucus, making it less suitable for implantation and more difficult for sperm to penetrate. This action helps prevent pregnancy.

Uses

Ethynodiol is primarily used in combination with estrogens in oral contraceptive pills. These pills are used to prevent pregnancy and may also be prescribed to regulate menstrual cycles, reduce menstrual cramps, and manage symptoms of premenstrual syndrome (PMS).

Side Effects

Common side effects of ethynodiol include nausea, headache, breast tenderness, and changes in menstrual bleeding. Some users may experience mood changes or weight gain. Serious side effects can include thrombosis, hypertension, and liver dysfunction.

Synthesis

The synthesis of ethynodiol involves the chemical modification of norethisterone. The process includes the introduction of an ethynyl group, which is crucial for its progestogenic activity. The synthesis pathway is depicted in the accompanying diagram.

Related pages

• Progestogen
• Oral contraceptive
• Norethisterone
• Estrogen