List of progestogens

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Steroid ring system.

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]

Compound Chemical name Structure
Progesterone Pregn-4-ene-3,20-dione Progesteron.svg
Quingestrone Progesterone 3-cyclopentyl enol ether Quingestrone.svg

Retroprogesterone derivatives[edit]

Compound Chemical name Structure
Retroprogesterone 9β,10α-Progesterone Retroprogesterone.svg
Dydrogesterone 6-Dehydro-9β,10α-progesterone Dydrogesterone.png
Trengestone 6-Chloro-6,7-didehydro-9β,10α-progesterone Trengestone.svg

Note that although an active progestogen, retroprogesterone is not medically used.

17α-Hydroxyprogesterone derivatives[edit]

Compound Chemical name Structure
Hydroxyprogesterone 17α-Hydroxyprogesterone 17-Hydroxyprogesterone.svg
Acetomepregenol (mepregenol diacetate) 3β,17α-Diacetoxy-6-methyl-6-dehydro-3-deketoprogesterone Acetomepregenol.svg
Algestone 16α,17α-Dihydroxyprogesterone Algestone.png
Algestone acetophenide 16α,17α-Dihydroxyprogesterone acetophenide Algestone acetophenide.png
Anagestone acetate 17α-Acetoxy-6α-methyl-3-deketoprogesterone Anagestone acetate.svg
Chlormadinone acetate 17α-Acetoxy-6-chloro-6-dehydroprogesterone Chlormadinone acetate.svg
Chlormethenmadinone acetate 17α-Acetoxy-6-chloro-16-methylene-6-dehydroprogesterone
Cyproterone acetate 17α-Acetoxy-1,2α-methylene-6-chloro-6-dehydroprogesterone Cyproterone acetate.svg
Delmadinone acetate 17α-Acetoxy-6-chloro-1,6-didehydro-progesterone Delmadinone acetate.svg
Flugestone acetate (flurogestone acetate) 17α-Acetoxy-9α-fluoro-11β-hydroxyprogesterone Flugestone acetate.svg
Flumedroxone acetate 17α-Acetoxy-6α-(trifluoromethyl)progesterone Flumedroxone acetate.svg
Hydroxyprogesterone acetate 17α-Acetoxyprogesterone 17-Acetoxyprogesterone.svg
Hydroxyprogesterone caproate 17α-Hexanoxyprogesterone Hydroxyprogesterone caproate.svg
Hydroxyprogesterone heptanoate 17α-Heptanoxyprogesterone Hydroxyprogesterone heptanoate.svg
Medroxyprogesterone acetate 17α-Acetoxy-6α-methylprogesterone Medroxyprogesterone 17-acetate.png
Megestrol acetate 17α-Acetoxy-6-methyl-6-dehydroprogesterone Megestrol acetate.svg
Melengestrol acetate 17α-Acetoxy-16-methylene-6-methyl-6-dehydroprogesterone Melengestrol acetate.png
Methenmadinone acetate 17α-Acetoxy-16-methylene-6-dehydroprogesterone
Osaterone acetate 17α-Acetoxy-6-chloro-2-oxa-6-dehydroprogesterone Osaterone skeletal.svg
Pentagestrone acetate 17α-Acetoxyprogesterone 3-cyclopentyl enol ether Pentagestrone acetate.svg

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[edit]

Compound Chemical name Structure
17α-Methylprogesterone 17α-Methylprogesterone Methylprogesterone.svg
Medrogestone 6,17α-Dimethyl-6-dehydroprogesterone Medrogestone.png

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[edit]

Compound Chemical name Structure
Haloprogesterone 6α-Fluoro-17α-bromoprogesterone Haloprogesterone.svg
Proligestone 14α,17α-Propylidenedioxyprogesterone Proligestone.svg

19-Norprogesterone derivatives[edit]

Compound Chemical name Structure
19-Norprogesterone 19-Norprogesterone 19-Norprogesterone.svg
Demegestone 17α-Methyl-9-dehydro-19-norprogesterone Demegestone.png
Gestonorone caproate (gestronol hexanoate) 17α-Caproxy-19-norprogesterone Gestronol caproate.svg
Nomegestrol acetate 17α-Acetoxy-6-methyl-6-dehydro-19-norprogesterone Nomegestrol acetate.svg
Norgestomet 17α-Acetoxy-11β-methyl-19-norprogesterone Norgestomet.svg
Promegestone 17α,21-Dimethyl-9-dehydro-19-norprogesterone Promegestone.png
Segesterone acetate (nestorone, elcometrine) 17α-Acetoxy-16-methylene-19-norprogesterone Nestorone.svg
Trimegestone 21β-Hydroxy-17α,21-dimethyl-9-dehydro-19-norprogesterone Trimegestone.png

Note that although an active progestogen, 19-norprogesterone is not medically used.

Testosterone derivatives[edit]

Compound Chemical name(s) Structure
Testosterone 17β-Deacetyl-17β-hydroxyprogesterone
Androst-4-en-17β-ol-3-one
Testosteron.svg

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[edit]

Compound Chemical name(s) Structure
Ethisterone (ethinyltestosterone) 17α-Ethynyltestosterone Ethisterone.svg
Danazol (2,3-isoxazolethisterone) 2,3-Isoxazol-17α-ethynyltestosterone? Danazol.svg
Dimethisterone 6α,21-Dimethyl-17α-ethynyltestosterone Dimethisterone.png

19-Nortestosterone derivatives[edit]

Compound Chemical name(s) Structure
Nandrolone (nortestosterone) 19-Nortestosterone Nandrolone.svg
Oxendolone (TSAA-291) 16β-Ethyl-19-nortestosterone Oxendolone.svg

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[edit]

Estranes[edit]

Compound Chemical name(s) Structure
Norethisterone (norethindrone) 17α-Ethynyl-19-nortestosterone Norethisterone.svg
Etynodiol diacetate (ethynodiol diacetate) 17α-Ethynyl-3-deketo-3β-hydroxy-19-nortestosterone 3β,17β-diacetate Ethynodiol diacetate.svg
Lynestrenol (3-deketonorethisterone) 17α-Ethynyl-3-deketo-19-nortestosterone Lynestrenol.svg
Norethisterone acetate (norethindrone acetate) 17α-Ethynyl-19-nortestosterone 17β-acetate Norethisterone acetate.svg
Norethisterone enanthate (norethindrone enanthate) 17α-Ethynyl-19-nortestosterone 17β-enanthate Norethindrone enanthate.svg
Noretynodrel (norethynodrel) 17α-Ethynyl-δ5(10)-19-nortestosterone Noretynodrel.svg
Norgestrienone (ethinyltrenbolone) 17α-Ethynyl-19-nor-δ9,11-testosterone Norgestrienone.svg
Quingestanol acetate 4-Hydro-17α-ethynyl-19-nor-δ3,5-testosterone 3-cyclopentyl ether 17β-acetate? Quingestanol acetate.svg
Tibolone (7α-methylnoretynodrel) 7α-Methyl-17α-ethynyl-19-nor-δ5(10)-testosterone Tibolone.svg

18-Methylestranes (13β-ethylgonanes)[edit]

Compound Chemical name(s) Structure
Desogestrel 3-Deketo-11-methylene-17α-ethynyl-18-methyl-19-nortestosterone Desogestrel.svg
Etonogestrel (3-ketodesogestrel) 11-Methylene-17α-ethynyl-18-methyl-19-nortestosterone Etonogestrel.svg
Gestodene (15-dehydronorgestrel) 17α-Ethynyl-18-methyl-19-nor-δ15-testosterone Gestodene.svg
Gestrinone (ethylnorgestrienone, R-2323) 17α-Ethynyl-18-methyl-19-nor-δ9,11-testosterone Gestrinone.svg
Levonorgestrel 17α-Ethynyl-18-methyl-19-nortestosterone Levonorgestrel.svg
Norelgestromin (17β-deacetylnorgestimate, norgestrel 3-oxime) 17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime Norelgestromin.svg
Norgestimate 17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime 17β-acetate Norgestimate.svg
Norgestrel (13-methylnorethisterone) rac-13-Ethyl-17α-ethynyl-19-nortestosterone Levonorgestrel.svg
Dextronorgestrel.svg

Other 17α-substituted 19-nortestosterone derivatives[edit]

Compound Chemical name(s) Structure
Allylestrenol (allyloestrenol) 3-Deketo-17α-allyl-19-nortestosterone Allylestrenol.svg
Altrenogest (allyltrenbolone, allyltrienolone) 17α-Allyl-19-nor-δ9,11-testosterone Altrenogest.svg
Dienogest 17α-Cyanomethyl-19-nor-δ9-testosterone Dienogest.svg
Normethandrone (methylestrenolone, normethandrolone, normethisterone, methylnortestosterone) 17α-Methyl-19-nortestosterone Methylestrenolone.svg
Norvinisterone (vinylnortestosterone, SC-4641) 17α-Vinyl-19-nortestosterone Norvinisterone.svg
Norgesterone (norvinodrel, vinylestrenolone, vinylnoretynodrel) 17α-Vinyl-δ5(10)-19-nortestosterone Norgesterone.svg

Spirolactone derivatives[edit]

Compound Chemical name(s) Structure
SC-5233 (spirolactone) 17α-(2-Carboxyethyl)testosterone γ-lactone SC-5233.svg
Drospirenone 6β,7β:15β,16β-Dimethylenespirolactone Drospirenone.svg

Note that although an active progestogen, SC-5233 (spirolactone) is not medically used.

See also[edit]

Notes[edit]

? = Chemical names that are unverified.

Further reading[edit]

  • McRobb L, Handelsman DJ, Kazlauskas R, Wilkinson S, McLeod MD, Heather AK (2008). "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay". J. Steroid Biochem. Mol. Biol. 110 (1-2): 39–47. doi:10.1016/j.jsbmb.2007.10.008. PMID 18395441.