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-6,7-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
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
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

  • 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. 


This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.