Etynodiol, or ethynodiol, is a steroidal progestin of the 19-nortestosterone group which was never marketed.[1][2][3] A diacylated derivative, etynodiol diacetate, is used as a hormonal contraceptive.[1][2] Etynodiol is sometimes used as a synonym for etynodiol diacetate.
Clinical data | |
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Other names | Ethynodiol; 3β-Hydroxynorethisterone; 17α-Ethynylestr-4-ene-3β,17β-diol |
Drug class | Progestin; Progestogen |
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CompTox Dashboard (EPA) |
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ECHA InfoCard | 100.013.610 |
Chemical and physical data | |
Formula | C20H28O2 |
Molar mass | 300.442 g·mol−1 |
3D model (JSmol) |
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It was patented in 1955.[4]
Etynodiol is a prodrug of norethisterone, and is converted immediately and completely into norethisterone.[5][6][7] Etynodiol is an intermediate in the conversion of the prodrug lynestrenol into norethisterone.[8]
Compound | Typea | PR | AR | ER | GR | MR | SHBG | CBG |
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Norethisterone | – | 67–75 | 15 | 0 | 0–1 | 0–3 | 16 | 0 |
5α-Dihydronorethisterone | Metabolite | 25 | 27 | 0 | 0 | ? | ? | ? |
3α,5α-Tetrahydronorethisterone | Metabolite | 1 | 0 | 0–1 | 0 | ? | ? | ? |
3α,5β-Tetrahydronorethisterone | Metabolite | ? | 0 | 0 | ? | ? | ? | ? |
3β,5α-Tetrahydronorethisterone | Metabolite | 1 | 0 | 0–8 | 0 | ? | ? | ? |
Ethinylestradiol | Metabolite | 15–25 | 1–3 | 112 | 1–3 | 0 | 0.18 | 0 |
Norethisterone acetate | Prodrug | 20 | 5 | 1 | 0 | 0 | ? | ? |
Norethisterone enanthate | Prodrug | ? | ? | ? | ? | ? | ? | ? |
Noretynodrel | Prodrug | 6 | 0 | 2 | 0 | 0 | 0 | 0 |
Etynodiol | Prodrug | 1 | 0 | 11–18 | 0 | ? | ? | ? |
Etynodiol diacetate | Prodrug | 1 | 0 | 0 | 0 | 0 | ? | ? |
Lynestrenol | Prodrug | 1 | 1 | 3 | 0 | 0 | ? | ? |
Notes: Values are percentages (%). Reference ligands (100%) were promegestone for the PR , metribolone for the AR , estradiol for the ER , dexamethasone for the GR , aldosterone for the MR , dihydrotestosterone for SHBG , and cortisol for CBG . Footnotes: a = Active or inactive metabolite, prodrug, or neither of norethisterone. Sources: See template. |
Etynodiol is a 19-nortestosterone derivative. Structurally, it is almost identical to norethisterone and lynestrenol, differing only in its C3 substituent. Whereas norethisterone has a ketone at C3 and lynestrenol has no substituent at C3, etynodiol has a hydroxyl group at the position.
Etynodiol is the generic name of the drug and its INN , while ethynodiol is its BAN .[1][2]