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.