Etynodiol, or ethynodiol, is a

steroid A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and a ...

progestin A progestogen, also referred to as a progestagen, gestagen, or gestogen, is a type of medication which produces effects similar to those of the natural product, natural female sex hormone progesterone in the body. A progestin is a ''synthetic co ...

of the 19-nortestosterone group which was never marketed. A diacylated derivative,

etynodiol diacetate Etynodiol diacetate, or ethynodiol diacetate, sold under the brand names Demulen and Femulen among others, is a progestin medication which is used in birth control pills. The medication is available only in combination with an estrogen. It is tak ...

, is used as a

hormonal contraceptive Hormonal contraception refers to birth control methods that act on the endocrine system. Almost all methods are composed of steroid hormones, although in India one selective estrogen receptor modulator is marketed as a contraceptive. The origin ...

. ''Etynodiol'' is sometimes used as a synonym for ''etynodiol diacetate''. It was patented in 1955.

Pharmacology

Etynodiol is a

prodrug A prodrug is a medication or compound that, after intake, is metabolized (i.e., converted within the body) into a pharmacologically active drug. Instead of administering a drug directly, a corresponding prodrug can be used to improve how the drug ...

norethisterone Norethisterone, also known as norethindrone and sold under many brand names, is a progestin medication used in birth control pills, menopausal hormone therapy, and for the treatment of gynecological disorders. The medication is available in both ...

, and is converted immediately and completely into norethisterone. Etynodiol is an intermediate in the conversion of the prodrug

lynestrenol Lynestrenol, sold under the brand names Exluton and Ministat among others, is a progestin medication which is used in birth control pills and in the treatment of gynecological disorders. The medication is available both alone and in combination ...

into norethisterone.

Chemistry

Etynodiol is a 19-nortestosterone derivative. Structurally, it is almost identical to norethisterone and

, differing only in its C3 substituent. Whereas norethisterone has a

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

at C3 and lynestrenol has no substituent at C3, etynodiol has a

hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy g ...

at the position.

Synthesis

Society and culture

Generic names

''Etynodiol'' is the generic name of the drug and its , while ''ethynodiol'' is its .

References

Ethynyl compounds Androgens and anabolic steroids Diols Estranes Prodrugs Progestogens Synthetic estrogens {{Genito-urinary-drug-stub