List of progestogens
This is a list of progestogens that are or that have been used in clinical or veterinary medicine. They are steroids and include derivatives of progesterone and testosterone.
Progesterone derivatives
[edit | edit source]| Compound | Chemical name | Structure |
|---|---|---|
| Progesterone | Pregn-4-ene-3,20-dione | File:Progesteron.svg |
| Quingestrone | Progesterone 3-cyclopentyl enol ether | File:Quingestrone.svg |
Retroprogesterone derivatives
[edit | edit source]| Compound | Chemical name | Structure |
|---|---|---|
| Retroprogesterone | 9β,10α-Progesterone | File:Retroprogesterone.svg |
| Dydrogesterone | 6-Dehydro-9β,10α-progesterone | File:Dydrogesterone.png |
| Trengestone | 6-Chloro-1,6-didehydro-9β,10α-progesterone | File:Trengestone.svg |
Although an active progestogen, retroprogesterone is not medically used.
17α-Hydroxyprogesterone derivatives
[edit | edit source]
17α-hydroxyprogesterone is inactive as a progestogen and is not used medically.
The 19-norprogesterone derivatives gestonorone caproate (gestronol hexanoate), nomegestrol acetate, segesterone acetate (nestorone, elcometrine), and norgestomet are also derivatives of 17α-hydroxyprogesterone (see below).
17α-Methylprogesterone derivatives
[edit | edit source]| Compound | Chemical name | Structure |
|---|---|---|
| 17α-Methylprogesterone | 17α-Methylprogesterone | File:Methylprogesterone.svg |
| Medrogestone | 6,17α-Dimethyl-6-dehydroprogesterone | File:Medrogestone.png |
Although an active progestogen, 17α-methylprogesterone is not medically used.
The 19-norprogesterone derivatives demegestone, promegestone, and trimegestone are also derivatives of 17α-methylprogesterone (see below).
Other 17α-substituted progesterone derivatives
[edit | edit source]| Compound | Chemical name | Structure |
|---|---|---|
| Haloprogesterone | 6α-Fluoro-17α-bromoprogesterone | File:Haloprogesterone.svg |
| Proligestone | 14α,17α-Propylidenedioxyprogesterone | File:Proligestone.svg |
19-Norprogesterone derivatives
[edit | edit source]| Compound | Chemical name | Structure |
|---|---|---|
| 19-Norprogesterone | 19-Norprogesterone | File:19-Norprogesterone.svg |
| Demegestone | 17α-Methyl-9-dehydro-19-norprogesterone | File:Demegestone.png |
| Gestonorone caproate (gestronol hexanoate) | 17α-Caproxy-19-norprogesterone | File:Gestronol caproate.svg |
| Nomegestrol acetate | 17α-Acetoxy-6-methyl-6-dehydro-19-norprogesterone | File:Nomegestrol acetate.svg |
| Norgestomet | 17α-Acetoxy-11β-methyl-19-norprogesterone | File:Norgestomet.svg |
| Promegestone | 17α,21-Dimethyl-9-dehydro-19-norprogesterone | File:Promegestone.png |
| Segesterone acetate (nestorone, elcometrine) | 17α-Acetoxy-16-methylene-19-norprogesterone | File:Nestorone.svg |
| Trimegestone | 21β-Hydroxy-17α,21-dimethyl-9-dehydro-19-norprogesterone | File:Trimegestone.png |
Although an active progestogen, 19-norprogesterone is not medically used.
Testosterone derivatives
[edit | edit source]| Compound | Chemical name(s) | Structure |
|---|---|---|
| Testosterone | 17β-Deacetyl-17β-hydroxyprogesterone Androst-4-en-17β-ol-3-one |
File:Testosteron.svg |
Testosterone itself does not have significant progestogenic activity. Testosterone is instead classified as an anabolic-androgenic steroid and is included here purely because it is the parent structure of this group of progestins.
17α-Ethynyltestosterone derivatives
[edit | edit source]| Compound | Chemical name(s) | Structure |
|---|---|---|
| Ethisterone (ethinyltestosterone) | 17α-Ethynyltestosterone | File:Ethisterone.svg |
| Danazol (2,3-isoxazolethisterone) | 2,3-Isoxazol-17α-ethynyltestosterone? | File:Danazol.svg |
| Dimethisterone | 6α,21-Dimethyl-17α-ethynyltestosterone | File:Dimethisterone.png |
19-Nortestosterone derivatives
[edit | edit source]| Compound | Chemical name(s) | Structure |
|---|---|---|
| Nandrolone (nortestosterone) | 19-Nortestosterone | File:Nandrolone.svg |
| Oxendolone (TSAA-291) | 16β-Ethyl-19-nortestosterone | File:Oxendolone.svg |
While nandrolone (19-nortestosterone) does have significant progestogenic activity, it is not used as a progestogen. It is instead classified as an androgenic-anabolic steroid and is included here purely because it is an important parent structure of this group of progestins.
17α-Ethynyl-19-nortestosterone derivatives
[edit | edit source]Estranes
[edit | edit source]
18-Methylestranes (13β-ethylgonanes)
[edit | edit source]| Compound | Chemical name(s) | Structure |
|---|---|---|
| Desogestrel | 3-Deketo-11-methylene-17α-ethynyl-18-methyl-19-nortestosterone | File:Desogestrel.svg |
| Etonogestrel (3-ketodesogestrel) | 11-Methylene-17α-ethynyl-18-methyl-19-nortestosterone | File:Etonogestrel.svg |
| Gestodene (15-dehydronorgestrel) | 17α-Ethynyl-18-methyl-19-nor-δ15-testosterone | File:Gestodene.svg |
| Gestrinone (ethylnorgestrienone, R-2323) | 17α-Ethynyl-18-methyl-19-nor-δ9,11-testosterone | File:Gestrinone.svg |
| Levonorgestrel | 17α-Ethynyl-18-methyl-19-nortestosterone | File:Levonorgestrel.svg |
| Norelgestromin (17β-deacetylnorgestimate, norgestrel 3-oxime) | 17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime | File:Norelgestromin.svg |
| Norgestimate | 17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime 17β-acetate | File:Norgestimate.svg |
| Norgestrel (13-methylnorethisterone) | rac-13-Ethyl-17α-ethynyl-19-nortestosterone | File:Levonorgestrel.svg File:Dextronorgestrel.svg |
Other 17α-substituted 19-nortestosterone derivatives
[edit | edit source]| Compound | Chemical name(s) | Structure |
|---|---|---|
| Allylestrenol (allyloestrenol) | 3-Deketo-17α-allyl-19-nortestosterone | File:Allylestrenol.svg |
| Altrenogest (allyltrenbolone, allyltrienolone) | 17α-Allyl-19-nor-δ9,11-testosterone | File:Altrenogest.svg |
| Dienogest | 17α-Cyanomethyl-19-nor-δ9-testosterone | File:Dienogest.svg |
| Normethandrone (methylestrenolone, normethandrolone, normethisterone, methylnortestosterone) | 17α-Methyl-19-nortestosterone | File:Methylestrenolone.svg |
| Norvinisterone (vinylnortestosterone, SC-4641) | 17α-Vinyl-19-nortestosterone | File:Norvinisterone.svg |
| Norgesterone (norvinodrel, vinylestrenolone, vinylnoretynodrel) | 17α-Vinyl-δ5(10)-19-nortestosterone | File:Norgesterone.svg |
Spirolactone derivatives
[edit | edit source]| Compound | Chemical name(s) | Structure |
|---|---|---|
| SC-5233 (spirolactone) | 17α-(2-Carboxyethyl)testosterone γ-lactone | File:SC-5233.svg |
| Drospirenone | 6β,7β:15β,16β-Dimethylenespirolactone | File:Drospirenone.svg |
Although an active progestogen, SC-5233 (spirolactone) is not medically used.
See also
[edit | edit source]Notes
[edit | edit source]? = Chemical names that are unverified.
Further reading
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