Chemistry: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
| Compound | Chemical name | Structure |
|---|---|---|
| Progesterone | Pregn-4-ene-3,20-dione | 
|
| Quingestrone | Progesterone 3-cyclopentyl enol ether | 
|
Retroprogesterone derivatives
| Compound | Chemical name | Structure |
|---|---|---|
| Retroprogesterone | 9β,10α-Progesterone | 
|
| Dydrogesterone | 6-Dehydro-9β,10α-progesterone | 
|
| Trengestone | 6-Chloro-1,6-didehydro-9β,10α-progesterone | 
|
Note that although an active progestogen, retroprogesterone is not medically used.
17α-Hydroxyprogesterone derivatives
| Compound | Chemical name | Structure |
|---|---|---|
| Hydroxyprogesterone | 17α-Hydroxyprogesterone | 
|
| Acetomepregenol (mepregenol diacetate) | 3β,17α-Diacetoxy-6-methyl-6-dehydro-3-deketoprogesterone | 
|
| Algestone | 16α,17α-Dihydroxyprogesterone | 
|
| Algestone acetophenide | 16α,17α-Dihydroxyprogesterone acetophenide | 
|
| Anagestone acetate | 17α-Acetoxy-6α-methyl-3-deketoprogesterone | 
|
| Chlormadinone acetate | 17α-Acetoxy-6-chloro-6-dehydroprogesterone | 
|
| Chlormethenmadinone acetate | 17α-Acetoxy-6-chloro-16-methylene-6-dehydroprogesterone | 
|
| Cyproterone acetate | 17α-Acetoxy-1,2α-methylene-6-chloro-6-dehydroprogesterone | 
|
| Delmadinone acetate | 17α-Acetoxy-6-chloro-1,6-didehydro-progesterone | 
|
| Flugestone acetate (flurogestone acetate) | 17α-Acetoxy-9α-fluoro-11β-hydroxyprogesterone | 
|
| Flumedroxone acetate | 17α-Acetoxy-6α-(trifluoromethyl)progesterone | 
|
| Hydroxyprogesterone acetate | 17α-Acetoxyprogesterone | 
|
| Hydroxyprogesterone caproate | 17α-Hexanoxyprogesterone | 
|
| Hydroxyprogesterone heptanoate | 17α-Heptanoxyprogesterone | 
|
| Medroxyprogesterone acetate | 17α-Acetoxy-6α-methylprogesterone | 
|
| Megestrol acetate | 17α-Acetoxy-6-methyl-6-dehydroprogesterone | 
|
| Melengestrol acetate | 17α-Acetoxy-16-methylene-6-methyl-6-dehydroprogesterone | 
|
| Methenmadinone acetate | 17α-Acetoxy-16-methylene-6-dehydroprogesterone | 
|
| Osaterone acetate | 17α-Acetoxy-6-chloro-2-oxa-6-dehydroprogesterone | 
|
| Pentagestrone acetate | 17α-Acetoxyprogesterone 3-cyclopentyl enol ether | 
|
Note that 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
| Compound | Chemical name | Structure |
|---|---|---|
| 17α-Methylprogesterone | 17α-Methylprogesterone | 
|
| Medrogestone | 6,17α-Dimethyl-6-dehydroprogesterone | 
|
Note that 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
| Compound | Chemical name | Structure |
|---|---|---|
| Haloprogesterone | 6α-Fluoro-17α-bromoprogesterone | 
|
| Proligestone | 14α,17α-Propylidenedioxyprogesterone | 
|
19-Norprogesterone derivatives
| Compound | Chemical name | Structure |
|---|---|---|
| 19-Norprogesterone | 19-Norprogesterone | 
|
| Demegestone | 17α-Methyl-9-dehydro-19-norprogesterone | 
|
| Gestonorone caproate (gestronol hexanoate) | 17α-Caproxy-19-norprogesterone | 
|
| Nomegestrol acetate | 17α-Acetoxy-6-methyl-6-dehydro-19-norprogesterone | 
|
| Norgestomet | 17α-Acetoxy-11β-methyl-19-norprogesterone | 
|
| Promegestone | 17α,21-Dimethyl-9-dehydro-19-norprogesterone | 
|
| Segesterone acetate (nestorone, elcometrine) | 17α-Acetoxy-16-methylene-19-norprogesterone | 
|
| Trimegestone | 21β-Hydroxy-17α,21-dimethyl-9-dehydro-19-norprogesterone | 
|
Note that although an active progestogen, 19-norprogesterone is not medically used.
Testosterone derivatives
| Compound | Chemical name(s) | Structure |
|---|---|---|
| Testosterone | 17β-Deacetyl-17β-hydroxyprogesterone Androst-4-en-17β-ol-3-one |
|
Note that 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
| Compound | Chemical name(s) | Structure |
|---|---|---|
| Ethisterone (ethinyltestosterone) | 17α-Ethynyltestosterone | 
|
| Danazol (2,3-isoxazolethisterone) | 2,3-Isoxazol-17α-ethynyltestosterone? | 
|
| Dimethisterone | 6α,21-Dimethyl-17α-ethynyltestosterone | 
|
19-Nortestosterone derivatives
| Compound | Chemical name(s) | Structure |
|---|---|---|
| Nandrolone (nortestosterone) | 19-Nortestosterone | 
|
| Oxendolone (TSAA-291) | 16β-Ethyl-19-nortestosterone | 
|
Note that 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
Estranes
| Compound | Chemical name(s) | Structure |
|---|---|---|
| Norethisterone (norethindrone) | 17α-Ethynyl-19-nortestosterone | 
|
| Etynodiol diacetate (ethynodiol diacetate) | 17α-Ethynyl-3-deketo-3β-hydroxy-19-nortestosterone 3β,17β-diacetate | 
|
| Lynestrenol (3-deketonorethisterone) | 17α-Ethynyl-3-deketo-19-nortestosterone | 
|
| Norethisterone acetate (norethindrone acetate) | 17α-Ethynyl-19-nortestosterone 17β-acetate | 
|
| Norethisterone enanthate (norethindrone enanthate) | 17α-Ethynyl-19-nortestosterone 17β-enanthate | 
|
| Noretynodrel (norethynodrel) | 17α-Ethynyl-δ5(10)-19-nortestosterone | 
|
| Norgestrienone (ethinyltrenbolone) | 17α-Ethynyl-19-nor-δ9,11-testosterone | 
|
| Quingestanol acetate | 4-Hydro-17α-ethynyl-19-nor-δ3,5-testosterone 3-cyclopentyl ether 17β-acetate? | 
|
| Tibolone (7α-methylnoretynodrel) | 7α-Methyl-17α-ethynyl-19-nor-δ5(10)-testosterone | 
|
18-Methylestranes (13β-ethylgonanes)
| Compound | Chemical name(s) | Structure |
|---|---|---|
| Desogestrel | 3-Deketo-11-methylene-17α-ethynyl-18-methyl-19-nortestosterone | 
|
| Etonogestrel (3-ketodesogestrel) | 11-Methylene-17α-ethynyl-18-methyl-19-nortestosterone | 
|
| Gestodene (15-dehydronorgestrel) | 17α-Ethynyl-18-methyl-19-nor-δ15-testosterone | 
|
| Gestrinone (ethylnorgestrienone, R-2323) | 17α-Ethynyl-18-methyl-19-nor-δ9,11-testosterone | 
|
| Levonorgestrel | 17α-Ethynyl-18-methyl-19-nortestosterone | 
|
| Norelgestromin (17β-deacetylnorgestimate, norgestrel 3-oxime) | 17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime | 
|
| Norgestimate | 17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime 17β-acetate | 
|
| Norgestrel (13-methylnorethisterone) | rac-13-Ethyl-17α-ethynyl-19-nortestosterone | 
|
Other 17α-substituted 19-nortestosterone derivatives
| Compound | Chemical name(s) | Structure |
|---|---|---|
| Allylestrenol (allyloestrenol) | 3-Deketo-17α-allyl-19-nortestosterone | 
|
| Altrenogest (allyltrenbolone, allyltrienolone) | 17α-Allyl-19-nor-δ9,11-testosterone | 
|
| Dienogest | 17α-Cyanomethyl-19-nor-δ9-testosterone | 
|
| Normethandrone (methylestrenolone, normethandrolone, normethisterone, methylnortestosterone) | 17α-Methyl-19-nortestosterone | 
|
| Norvinisterone (vinylnortestosterone, SC-4641) | 17α-Vinyl-19-nortestosterone | 
|
| Norgesterone (norvinodrel, vinylestrenolone, vinylnoretynodrel) | 17α-Vinyl-δ5(10)-19-nortestosterone | 
|
Spirolactone derivatives
| Compound | Chemical name(s) | Structure |
|---|---|---|
| SC-5233 (spirolactone) | 17α-(2-Carboxyethyl)testosterone γ-lactone | 
|
| Drospirenone | 6β,7β:15β,16β-Dimethylenespirolactone | 
|
Note that although an active progestogen, SC-5233 (spirolactone) is not medically used.
See also
Notes
? = Chemical names that are unverified.
Further reading
- "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay". J. Steroid Biochem. Mol. Biol. 110 (1–2): 39–47. 2008. doi:10.1016/j.jsbmb.2007.10.008. PMID 18395441.
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