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List of progestogens

From Wikipedia, the free encyclopedia
(Redirected fromList of steroidal progestogens)

Progesterone.
Steroid ring system.

This is alist ofprogestogens that are or that have been used inclinical orveterinary medicine. They aresteroids and includederivatives ofprogesterone andtestosterone.

Progesterone derivatives

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CompoundChemical nameStructure
ProgesteronePregn-4-ene-3,20-dione
QuingestroneProgesterone 3-cyclopentyl enol ether

Retroprogesterone derivatives

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CompoundChemical nameStructure
Retroprogesterone9β,10α-Progesterone
Dydrogesterone6-Dehydro-9β,10α-progesterone
Trengestone6-Chloro-1,6-didehydro-9β,10α-progesterone

Although an active progestogen, retroprogesterone is not medically used.

17α-Hydroxyprogesterone derivatives

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CompoundChemical nameStructure
Hydroxyprogesterone17α-Hydroxyprogesterone
Acetomepregenol (mepregenol diacetate)3β,17α-Diacetoxy-6-methyl-6-dehydro-3-deketoprogesterone
Algestone16α,17α-Dihydroxyprogesterone
Algestone acetophenide16α,17α-Dihydroxyprogesterone acetophenide
Anagestone acetate17α-Acetoxy-6α-methyl-3-deketoprogesterone
Chlormadinone acetate17α-Acetoxy-6-chloro-6-dehydroprogesterone
Chlormethenmadinone acetate17α-Acetoxy-6-chloro-16-methylene-6-dehydroprogesterone
Cyproterone acetate17α-Acetoxy-1,2α-methylene-6-chloro-6-dehydroprogesterone
Delmadinone acetate17α-Acetoxy-6-chloro-1,6-didehydro-progesterone
Flugestone acetate (flurogestone acetate)17α-Acetoxy-9α-fluoro-11β-hydroxyprogesterone
Flumedroxone acetate17α-Acetoxy-6α-(trifluoromethyl)progesterone
Hydroxyprogesterone acetate17α-Acetoxyprogesterone
Hydroxyprogesterone caproate17α-Hexanoxyprogesterone
Hydroxyprogesterone heptanoate17α-Heptanoxyprogesterone
Medroxyprogesterone acetate17α-Acetoxy-6α-methylprogesterone
Megestrol acetate17α-Acetoxy-6-methyl-6-dehydroprogesterone
Melengestrol acetate17α-Acetoxy-16-methylene-6-methyl-6-dehydroprogesterone
Methenmadinone acetate17α-Acetoxy-16-methylene-6-dehydroprogesterone
Osaterone acetate17α-Acetoxy-6-chloro-2-oxa-6-dehydroprogesterone
Pentagestrone acetate17α-Acetoxyprogesterone 3-cyclopentyl enol ether

17α-hydroxyprogesterone is inactive as a progestogen and is not used medically.

The 19-norprogesterone derivativesgestonorone caproate (gestronol hexanoate),nomegestrol acetate,segesterone acetate (nestorone, elcometrine), andnorgestomet are also derivatives of 17α-hydroxyprogesterone (seebelow).

17α-Methylprogesterone derivatives

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CompoundChemical nameStructure
17α-Methylprogesterone17α-Methylprogesterone
Medrogestone6,17α-Dimethyl-6-dehydroprogesterone

Although an active progestogen, 17α-methylprogesterone is not medically used.

The 19-norprogesterone derivativesdemegestone,promegestone, andtrimegestone are also derivatives of 17α-methylprogesterone (seebelow).

Other 17α-substituted progesterone derivatives

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CompoundChemical nameStructure
Haloprogesterone6α-Fluoro-17α-bromoprogesterone
Proligestone14α,17α-Propylidenedioxyprogesterone

19-Norprogesterone derivatives

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CompoundChemical nameStructure
19-Norprogesterone19-Norprogesterone
Demegestone17α-Methyl-9-dehydro-19-norprogesterone
Gestonorone caproate (gestronol hexanoate)17α-Caproxy-19-norprogesterone
Nomegestrol acetate17α-Acetoxy-6-methyl-6-dehydro-19-norprogesterone
Norgestomet17α-Acetoxy-11β-methyl-19-norprogesterone
Promegestone17α,21-Dimethyl-9-dehydro-19-norprogesterone
Segesterone acetate (nestorone, elcometrine)17α-Acetoxy-16-methylene-19-norprogesterone
Trimegestone21β-Hydroxy-17α,21-dimethyl-9-dehydro-19-norprogesterone

Although an active progestogen, 19-norprogesterone is not medically used.

Testosterone derivatives

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CompoundChemical name(s)Structure
Testosterone17β-Deacetyl-17β-hydroxyprogesterone
Androst-4-en-17β-ol-3-one

Testosterone itself does not have significant progestogenic activity. Testosterone is instead classified as ananabolic-androgenic steroid and is included here purely because it is the parent structure of this group of progestins.

17α-Ethynyltestosterone derivatives

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CompoundChemical name(s)Structure
Ethisterone (ethinyltestosterone)17α-Ethynyltestosterone
Danazol (2,3-isoxazolethisterone)2,3-Isoxazol-17α-ethynyltestosterone?
Dimethisterone6α,21-Dimethyl-17α-ethynyltestosterone

19-Nortestosterone derivatives

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CompoundChemical name(s)Structure
Nandrolone (nortestosterone)19-Nortestosterone
Oxendolone (TSAA-291)16β-Ethyl-19-nortestosterone

Whilenandrolone (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

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Estranes

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CompoundChemical 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 acetate4-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)

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CompoundChemical name(s)Structure
Desogestrel3-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
Levonorgestrel17α-Ethynyl-18-methyl-19-nortestosterone
Norelgestromin (17β-deacetylnorgestimate, norgestrel 3-oxime)17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime
Norgestimate17α-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

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CompoundChemical name(s)Structure
Allylestrenol (allyloestrenol)3-Deketo-17α-allyl-19-nortestosterone
Altrenogest (allyltrenbolone, allyltrienolone)17α-Allyl-19-nor-δ9,11-testosterone
Dienogest17α-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

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CompoundChemical name(s)Structure
SC-5233 (spirolactone)17α-(2-Carboxyethyl)testosterone γ-lactone
Drospirenone6β,7β:15β,16β-Dimethylenespirolactone

Although an active progestogen, SC-5233 (spirolactone) is not medically used.

See also

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Notes

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? = Chemical names that are unverified.

Further reading

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  • 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.S2CID 5612000.
Progestogens
(andprogestins)
PRTooltip Progesterone receptoragonists
Antiprogestogens
SPRMsTooltip Selective progesterone receptor modulators
PRTooltip Progesterone receptorantagonists
PRTooltip Progesterone receptor
Agonists
Mixed
(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
Agonists
Antagonists
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