 | |
| Clinical data | |
|---|---|
| Other names | Ethynodiol; 3β-Hydroxynorethisterone; 17α-Ethynylestr-4-ene-3β,17β-diol |
| Drug class | Progestin;Progestogen |
| ATC code | |
| Identifiers | |
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| CAS Number | |
| ChemSpider | |
| UNII | |
| CompTox Dashboard(EPA) | |
| 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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Etynodiol, orethynodiol, is asteroidalprogestin of the19-nortestosterone group which was never marketed.[1][2][3] Adiacylated derivative,etynodiol diacetate, is used as ahormonal contraceptive.[1][2]Etynodiol is sometimes used as a synonym foretynodiol diacetate.
It was patented in 1955.[4]
Etynodiol is aprodrug ofnorethisterone, and is converted immediately and completely into norethisterone.[5][6][7] Etynodiol is anintermediate in the conversion of the prodruglynestrenol into norethisterone.[8]
| Compound | Typea | PRTooltip Progesterone receptor | ARTooltip Androgen receptor | ERTooltip Estrogen receptor | GRTooltip Glucocorticoid receptor | MRTooltip Mineralocorticoid receptor | SHBGTooltip Sex hormone-binding globulin | CBGTooltip Corticosteroid binding globulin |
|---|---|---|---|---|---|---|---|---|
| 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 (%). Referenceligands (100%) werepromegestone for thePRTooltip progesterone receptor,metribolone for theARTooltip androgen receptor,estradiol for theERTooltip estrogen receptor,dexamethasone for theGRTooltip glucocorticoid receptor,aldosterone for theMRTooltip mineralocorticoid receptor,dihydrotestosterone forSHBGTooltip sex hormone-binding globulin, andcortisol forCBGTooltip Corticosteroid-binding globulin.Footnotes:a =Active or inactivemetabolite,prodrug, or neither of norethisterone.Sources: See template. | ||||||||
Etynodiol is a 19-nortestosterone derivative. Structurally, it is almost identical to norethisterone andlynestrenol, differing only in its C3 substituent. Whereas norethisterone has aketone at C3 and lynestrenol has no substituent at C3, etynodiol has ahydroxyl group at the position.
Etynodiol is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name, whileethynodiol is itsBANTooltip British Approved Name.[1][2]