List of progestogens

Short description: none

Progesterone. 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.

## Contents

* 1 Progesterone derivatives
* 1.1 Retroprogesterone derivatives
* 1.2 17α-Hydroxyprogesterone derivatives
* 1.3 17α-Methylprogesterone derivatives
* 1.4 Other 17α-substituted progesterone derivatives
* 1.5 19-Norprogesterone derivatives
* 2 Testosterone derivatives
* 2.1 17α-Ethynyltestosterone derivatives
* 2.2 19-Nortestosterone derivatives
* 2.3 17α-Ethynyl-19-nortestosterone derivatives
* 2.3.1 Estranes
* 2.3.2 18-Methylestranes (13β-ethylgonanes)
* 2.4 Other 17α-substituted 19-nortestosterone derivatives
* 3 Spirolactone derivatives
* 4 See also
* 5 Notes
* 6 Further reading

## 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

* List of steroids
* List of progestogen esters

## Notes

? = Chemical names that are unverified.

## Further reading

* "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay". J. Steroid Biochem. Mol. Biol. 110 (1–2): 39–47. 2008. doi:10.1016/j.jsbmb.2007.10.008. PMID 18395441.

* v
* t
* e

Progestogens and antiprogestogens

Progestogens
(and progestins)|

| PR agonists|

* Progesterone derivatives: Progesterone
* Quingestrone

* Retroprogesterone derivatives: Dydrogesterone
* Trengestone

* 17α-Hydroxyprogesterone (and closely related) derivatives: 17α-Hydroxylated: Acetomepregenol (mepregenol diacetate)
* Algestone acetophenide (dihydroxyprogesterone acetophenide)
* Anagestone acetate
* Chlormadinone acetate
* Chlormethenmadinone acetate
* Cyproterone acetate
* Delmadinone acetate
* Flugestone acetate (flurogestone acetate)
* Flumedroxone acetate
* Hydroxyprogesterone acetate
* Hydroxyprogesterone caproate
* Hydroxyprogesterone heptanoate
* Medroxyprogesterone acetate#
* Megestrol acetate
* Melengestrol acetate
* Methenmadinone acetate
* Osaterone acetate
* Pentagestrone acetate
* Proligestone; 17α-Methylated: Medrogestone; Others: Haloprogesterone

* 19-Norprogesterone derivatives: 17α-Hydroxylated: Gestonorone caproate (gestronol hexanoate)
* Nomegestrol acetate
* Norgestomet
* Segesterone acetate (nestorone, elcometrine); 17α-Methylated: Demegestone
* Promegestone
* Trimegestone

* Testosterone derivatives: Estranes: Danazol
* Dimethisterone
* Ethisterone

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

* Spirolactone derivatives: Drospirenone

* Others: Anabolic–androgenic steroids (e.g., nandrolone and esters, trenbolone and esters, ethylestrenol, norethandrolone, others)

|

Antiprogestogens|

| SPRMs|

* Telapristone§
* Ulipristal acetate

|

PR antagonists|

* Aglepristone
* Mifepristone

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

See also
Progesterone receptor modulators
Androgens and antiandrogens
Estrogens and antiestrogens
List of progestogens

* v
* t
* e

Progesterone receptor modulators

PR|

| Agonists|

* Progesterone derivatives: 3β-Dihydroprogesterone
* 5α-Dihydroprogesterone
* 9α-Bromo-11-ketoprogesterone
* 11-Dehydroprogesterone
* 11-Deoxycorticosterone
* 16α-Hydroxyprogesterone
* 20α-Dihydroprogesterone
* 20β-Dihydroprogesterone
* Dimepregnen
* Diosgenin
* P1-185
* Progesterone
* Progesterone 3-acetyl enol ether
* Quingestrone

* Retroprogesterone derivatives: 20α-Dihydrodydrogesterone
* 20α-Dihydrotrengestone
* DU-41164
* DU-41165
* Dydrogesterone
* Retroprogesterone
* Ro 6-3129
* Trengestone

* 17α-Substituted progesterone derivatives: 6α-Methyl-17α-bromoprogesterone
* 15β-Hydroxycyproterone acetate
* 16-Methylene-17α-hydroxyprogesterone acetate
* 17α-Bromoprogesterone
* 17α-Hydroxyprogesterone (hydroxyprogesterone)
* 17α-Methylprogesterone
* Acetomepregenol (mepregenol diacetate)
* Algestone
* Algestone acetonide
* Algestone acetophenide
* Anagestone
* Anagestone acetate
* Bromethenmadinone
* Bromethenmadinone acetate
* Butagest (buterol)
* Chlormadinone
* Chlormadinone acetate
* Chlormadinone caproate
* Chlormethenmadinone
* Chlormethenmadinone acetate
* Cismadinone
* Cismadinone acetate
* Clogestone
* Clogestone acetate
* Clomegestone
* Clomegestone acetate
* Cymegesolate
* Cyproterone acetate
* Delmadinone
* Delmadinone acetate
* Edogestrone
* Flugestone
* Flugestone acetate
* Fluorometholone
* Fluorometholone acetate
* Flumedroxone
* Flumedroxone acetate
* Fluoromedroxyprogesterone acetate
* Gestaclone
* Haloprogesterone
* Hydromadinone
* Hydromadinone acetate
* Hydroxyprogesterone acetate
* Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate)
* Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)
* Hydroxyprogesterone heptanoate benzilic acid hydrazone
* Mecigestone (pentarane B)
* Medrogestone
* Medroxyprogesterone
* Medroxyprogesterone acetate
* Medroxyprogesterone caproate
* Megestrol
* Megestrol acetate
* Megestrol caproate
* Melengestrol
* Melengestrol acetate
* Methenmadinone
* Methenmadinone acetate
* Methenmadinone caproate
* Mometasone
* Mometasone furoate
* Osaterone
* Osaterone acetate
* Pentagestrone
* Pentagestrone acetate
* Pentarane A
* Proligestone

* 19-Norprogesterone derivatives: 17α-Methyl-19-norprogesterone
* 18-Methylsegesterone acetate
* 19-Norprogesterone
* Amadinone
* Amadinone acetate
* Demegestone
* Fluoro ethyl norprogesterone
* Fluoro furanyl norprogesterone
* Gestadienol
* Gestadienol acetate
* Gestonorone acetate (gestronol acetate)
* Gestonorone caproate (gestronol hexanoate)
* Gestronol (gestonorone)
* Nomegestrol
* Nomegestrol acetate
* Norgestomet
* ORG-2058
* Oxogestone
* Oxogestone phenpropionate (xinogestone)
* Promegestone
* Segesterone
* Segesterone acetate (nestorone)
* Trimegestone

* Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
* 6,6-Difluoronorethisterone acetate
* 17α-Allyl-19-nortestosterone
* Allylestrenol
* Altrenogest
* Chloroethynylnorgestrel
* Cingestol
* Danazol
* Desogestrel
* Dienogest
* Ethisterone
* Ethynerone
* Etonogestrel
* Etynodiol
* Etynodiol diacetate
* Gestodene
* Gestrinone
* Levonorgestrel
* Levonorgestrel esters (e.g., levonorgestrel butanoate)
* Lynestrenol
* Lynestrenol phenylpropionate
* Metynodiol
* Metynodiol diacetate
* Norelgestromin
* Norethisterone (norethindrone)
* Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate)
* Noretynodrel
* Norgesterone
* Norgestimate
* Norgestrel
* Norgestrienone
* Norvinisterone
* Oxendolone
* Quingestanol
* Quingestanol acetate
* Tibolone
* Tigestol
* Tosagestin; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
* 11β-Methyl-19-nortestosterone dodecylcarbonate
* 19-Nor-5-androstenediol
* 19-Nor-5-androstenedione
* 19-Nordehydroepiandrosterone
* Bolandiol
* Bolandiol dipropionate
* Bolandione
* Dimethisterone
* Dienedione
* Dienolone
* Dimethandrolone
* Dimethandrolone buciclate
* Dimethandrolone dodecylcarbonate
* Dimethandrolone undecanoate
* Dimethyldienolone
* Dimethyltrienolone
* Ethyldienolone
* Ethylestrenol (ethylnandrol)
* Methyldienolone
* Metribolone (R-1881)
* Methoxydienone (methoxygonadiene)
* Mibolerone
* Nandrolone
* Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate)
* Norethandrolone
* Normethandrone (methylestrenolone, normethandrolone, normethisterone)
* RU-2309
* Tetrahydrogestrinone
* Trenbolone (trienolone)
* Trenbolone esters (e.g., trenbolone acetate, trenbolone enanthate)
* Trendione
* Trestolone
* Trestolone acetate

* Spirolactone derivatives: Canrenoic acid
* Canrenone
* Drospirenone
* Mespirenone
* Potassium canrenoate
* Prorenone
* SC-5233 (spirolactone)
* SC-8109
* Spironolactone
* Spirorenone

* Nonsteroidal: 3,8-Dihydrodiligustilide
* LG-2527
* LG-100128
* Riligustilide
* RWJ-26819
* RWJ-49853
* RWJ-60130
* Tanaproget
* ZM-182345

* Unknown: ORG-47241
* ORG-201745

|

Mixed
(SPRMs)|

* Steroidal: Dihydroethisterone
* 5α-Dihydrolevonorgestrel
* 5α-Dihydronorethisterone
* Asoprisnil
* Asoprisnil ecamate
* Guggulsterone
* J1042
* LG-120838
* Metapristone (RU-42633)
* Mifepristone (RU-486)
* ORF-9371
* ORF-9326
* ORG-31710
* ORG-33628
* RMI-12936
* Telapristone
* Ulipristal acetate
* Vilaprisan
* ZK-137316

* Nonsteroidal: Apigenin
* Kaempferol
* LG-120920
* Naringenin
* PRA-910
* Syringic acid

Antagonists|

* Steroidal: Aglepristone
* Lilopristone
* Lonaprisan
* Onapristone
* ORG-31710
* ORG-31806
* ORG-33628
* RTI 3021–022
* Toripristone
* Zanoterone

* Nonsteroidal: Darolutamide
* LG-001447
* LG-100127
* LG-100128
* LG-120830
* LG-121046
* Valproic acid
* ZM-150271
* ZM-172406

mPR
(PAQR)|

| Agonists|

* 5α-Dihydroprogesterone
* 5β-Dihydroprogesterone
* 11-Deoxycortisone (21-hydroxyprogesterone)
* 11-Deoxycortisol (17α,21-dihydroxyprogesterone)
* 17α-Hydroxyprogesterone
* Allopregnanolone
* Mifepristone
* Pregnenolone
* Progesterone

|

Antagonists|

* Mifepristone

See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens

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