List of steroidal progestogens

Steroid ring system.

This is a list of steroidal progestogens or progesterone derivatives that are or have been used in clinical or veterinary medicine.

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
Hydroxyprogesterone acetate	17α-Acetoxyprogesterone
Hydroxyprogesterone caproate	17α-Hexanoxyprogesterone
Hydroxyprogesterone heptanoate	17α-Heptanoxyprogesterone
Medroxyprogesterone	17α-Hydroxy-6α-methylprogesterone
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

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	21-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 androgenic-anabolic steroid and is included here purely because it is the parent structure of this group of progestins.

17α-Ethynylated testosterone 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-Ethynylated 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-δ^9,11-testosterone
Quingestanol acetate	4-Hydro-17α-ethynyl-19-nor-δ^3,5-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-δ^9,11-testosterone
Levonorgestrel ((−)-norgestrel)	(−)-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 (18-methylnorethisterone)	17α-Ethynyl-18-methyl-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-δ^9,11-testosterone
Dienogest	17α-Cyanomethyl-19-nor-δ⁹-testosterone
Norethandrolone (ethylnortestosterone)	17α-Ethyl-19-nortestosterone
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
Spironolactone	7α-Acetylthiospirolactone

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

Notes

^? = Chemical names that are unverified.

Progesterone	Progesterone Quingestrone

Retroprogesterone	Dydrogesterone Trengestone

17α-Hydroxyprogesterone (and closely related)	Acetomepregenol (mepregenol diacetate) Algestone Algestone acetophenide Anagestone acetate Chlormadinone acetate Cyproterone acetate Delmadinone acetate Flugestone acetate (flurogestone acetate) Hydroxyprogesterone Hydroxyprogesterone acetate Hydroxyprogesterone caproate Hydroxyprogesterone heptanoate Medroxyprogesterone Medroxyprogesterone acetate^# Megestrol acetate Melengestrol acetate Osaterone acetate Pentagestrone acetate Other 17α-substitutions: Haloprogesterone Medrogestone Proligestone

19-Norprogesterone (incl. 17α-substituted)	Demegestone Gestonorone caproate (gestronol hexanoate) Nomegestrol acetate Norgestomet Promegestone Segesterone acetate (nestorone) Trimegestone

17α-Ethynyltestosterone	Danazol Dimethisterone Ethisterone

19-Nortestosterone	Estranes: Etynodiol diacetate Gestrinone Lynestrenol Norethisterone (norethindrone)^# Norethisterone acetate Norethisterone enanthate Noretynodrel Norgestrienone Quingestanol acetate Tibolone Gonanes: Desogestrel Dienogest Etonogestrel Gestodene Levonorgestrel^# Norelgestromin Norgestimate Norgestrel Others: Allylestrenol Altrenogest Norgesterone Normethandrone (methylestrenolone) Norvinisterone Oxendolone

17α-Spirolactosteroid	Canrenone Drospirenone Potassium canrenoate Spironolactone

Others	Anabolic steroids (e.g., nandrolone esters, trenbolone esters, norethandrolone, normethandrone, propetandrol, others)

SPRMs

Antiprogestogens

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: Androgens and antiandrogens • Estrogens and antiestrogens • Glucocorticoids and antiglucocorticoids • Mineralocorticoids and antimineralocorticoids • Gonadotropins and GnRH

Progesterone receptor modulators

Agonists	Progesterone derivatives: 5α-Dihydroprogesterone 9α-Bromo-11-ketoprogesterone 11-Dehydroprogesterone 11-Deoxycorticosterone 20α-Dihydroprogesterone Dimepregnen Diosgenin Progesterone Quingestrone Retroprogesterone derivatives: Dydrogesterone Retroprogesterone Ro 6-3129 Trengestone 17α-Substituted progesterone derivatives: 17α-Hydroxyprogesterone (hydroxyprogesterone) 17α-Methylprogesterone Acetomepregenol (mepregenol diacetate) Algestone Algestone acetonide Algestone acetophenide Amadinone Amadinone acetate Anagestone Anagestone acetate Butagest (buterol) Chlormadinone Chlormadinone acetate Cismadinone Cismadinone acetate Clogestone Clogestone acetate Clomegestone Clomegestone acetate Cyproterone acetate Delmadinone Delmadinone acetate Edogestrone Flugestone Flugestone acetate Flumedroxone Flumedroxone acetate Gestaclone Haloprogesterone Hydromadinone (hydromadinone acetate) Hydroxyprogesterone acetate Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate) Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate) Mecigestone (pentarane B) Medrogestone Medroxyprogesterone Medroxyprogesterone acetate Megestrol Megestrol acetate Melengestrol Melengestrol acetate Mometasone Mometasone furoate Osaterone Osaterone acetate Pentagestrone Pentagestrone acetate Pentarane A Proligestone 19-Norprogesterone derivatives: 19-Norprogesterone Demegestone Gestadienol Gestonorone caproate (gestronol hexanoate) Gestronol (gestonorone) Nomegestrol Nomegestrol acetate Norgestomet Org-2058 Oxogestone Oxogestone phenpropionate Promegestone Segesterone Segesterone acetate (nestorone) Trimegestone Testosterone derivatives: 6,6-Difluoronorethisterone 11β-Methyl-19-nortestosterone 11β-Methyl-19-nortestosterone dodecylcarbonate 19-Nor-5-androstenediol 19-Nor-5-androstenedione Δ^4-Tibolone Allylestrenol Altrenogest Bolandiol Bolandiol dipropionate Bolandione Chloroethynyl norgestrel Cingestol Danazol Desogestrel Dienedione Dienogest Dienolone Dimethandrolone Dimethandrolone buciclate Dimethandrolone dodecylcarbonate Dimethandrolone undecanoate Dimethisterone Dimethyltrienolone Ethisterone Ethyldienolone Ethylestrenol (ethylnandrol) Ethynerone Etonogestrel Etynodiol Etynodiol diacetate Gestodene Gestrinone Levonorgestrel Levonorgestrel butanoate Lynestrenol Methyldienolone Metribolone (R-1881) Metynodiol Metynodiol diacetate Methoxydienone (methoxygonadiene) Mibolerone Nandrolone Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate) Norelgestromin Norethisterone (norethindrone) Norethisterone acetate Norethisterone acetate oxime Norethisterone enanthate Noretynodrel Norgesterone Norgestimate Norgestrel Norgestrienone Normethandrone (methylestrenolone, normethandrolone, normethisterone) Norvinisterone Oxendolone Quingestanol Quingestanol acetate Tetrahydrogestrinone Tibolone Tigestol Tosagestin Trenbolone (trienolone) Trestolone Trestolone acetate Spirolactone derivatives: Canrenoic acid Canrenone Drospirenone Mespirenone Potassium canrenoate SC-5233 SC-8109 Spironolactone Spirorenone Non-steroidal: 3,8-Dihydrodiligustilide Riligustilide Tanaproget ZM-182345

Mixed (SPRMs)	Apigenin Asoprisnil Asoprisnil ecamate Guggulsterone Kaempferol J1042 LG-120838 Naringenin PRA-910 Syringic acid Telapristone Antagonistic: Mifepristone Org-31710 Org-33628 Ulipristal acetate ZK-137316

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone Aglepristone Lilopristone Lonaprisan Onapristone Toripristone Valproic acid Vilaprisan Zanoterone ZM-150271 ZM-172406

mPRs
(PAQRs)

Agonists	5α-Dihydroprogesterone 5β-Dihydroprogesterone 11-Deoxycorticosterone 17α-Hydroxyprogesterone 17α,21-Dihydroxyprogesterone 21-Hydroxyprogesterone Allopregnanolone Mifepristone Pregnenolone Progesterone

Antagonists	Mifepristone

See also: Androgenics • Estrogenics • Glucocorticoidics • Mineralocorticoidics • Steroid hormone metabolism modulators

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