List of progestogen esters

Short description: None

Norethisterone acetate, a widely used progestogen ester and prodrug of norethisterone. Medroxyprogesterone acetate, a progestogen ester that does not act as a prodrug.

This is a list of progestogen esters, or esters of progestogens.[1][2][3][4]

Unlike the case of testosterone and estradiol, progesterone cannot be esterified as it lacks hydroxyl groups, so all progestogen esters, with the exception of esters of 17α-hydroxyprogesterone like hydroxyprogesterone caproate, are esters of progestins (synthetic progestogens) and are non-bioidentical. In addition, whereas all androgen and estrogen esters are prodrugs of the parent compound, only some and not all progestogen esters act as prodrugs. Esters of 17α-hydroxyprogesterone and 19-norprogesterone derivatives like hydroxyprogesterone caproate, medroxyprogesterone acetate, and nomegestrol acetate are active themselves and are not prodrugs, whereas esters of 19-nortestosterone derivatives like norethisterone acetate and norethisterone enanthate are not active themselves and are prodrugs.

## Contents

* 1 Esters of progesterone derivatives
* 1.1 Esters of 17α-hydroxyprogesterone derivatives
* 1.1.1 Marketed
* 1.1.2 Never marketed
* 1.2 Esters of 19-norprogesterone derivatives
* 1.2.1 Marketed
* 1.2.2 Never marketed
* 2 Esters of testosterone derivatives
* 2.1 Esters of 19-nortestosterone derivatives
* 2.1.1 Marketed
* 2.1.2 Never marketed
* 3 Other conjugates of progesterone derivatives
* 3.1 Ethers of progesterone derivatives
* 3.1.1 Marketed
* 3.1.2 Never marketed
* 3.2 Cyclic ketals of progesterone derivatives
* 3.2.1 Marketed
* 3.3 Oximes of progesterone derivatives
* 3.3.1 Never marketed
* 4 Other conjugates of testosterone derivatives
* 4.1 Oximes of 19-nortestosterone derivatives
* 4.1.1 Marketed
* 4.1.2 Never marketed
* 5 See also
* 6 References

## Esters of progesterone derivatives

### Esters of 17α-hydroxyprogesterone derivatives

#### Marketed

The following major progestogen esters have been marketed:

* Chlormadinone acetate (Prostal, Belara)
* Cyproterone acetate (Androcur, Cyprostat, Diane, Diane-35)
* Hydroxyprogesterone caproate (Proluton, Proluton Depot, Makena; Delalutin)
* Medroxyprogesterone acetate (Depo-Provera, Provera)
* Megestrol acetate (Megace)

And the following minor progestogen esters have been marketed:

* Acetomepregenol (mepregenol diacete; Diamol)
* Anagestone acetate (Anatropin; ORF-1658)
* Chlormethenmadinone acetate (Biogest, Agelin)
* Flumedroxone acetate (Demigran, Leomigran; WG-537)
* Hydroxyprogesterone acetate (acetoxyprogesterone; Prodox)
* Hydroxyprogesterone heptanoate (H.O.P., Lutogil A.P., Lutogyl A.P.)
* Methenmadinone acetate (Superlutin, Antigest)
* Pentagestrone acetate (Gestovis, Gestovister)

The following veterinary-only progestogen esters have also been marketed:

* Delmadinone acetate (Tardak)
* Flugestone acetate (Chronogest, Chrono-Gest, Cronolone, Synchro-Mate, Gyncro-Mate; NSC-65411, SC-9880)
* Melengestrol acetate (Heifermax, MGA)
* Osaterone acetate (Ypozane; TZP-4238)

The corticosteroid ester mometasone furoate (Asmanex, Elocom, Elocon, Elosalic, Nasonex), which is a 17α-hydroxyprogesterone derivative, also has very potent progestogenic activity, though it is not used as a progestogen and is instead used exclusively as a corticosteroid.[5]

#### Never marketed

* Bromethenmadinone acetate
* Butagest (buterol)
* Chlormadinone caproate
* Cismadinone acetate
* Clogestone acetate (chlormadinol acetate; AY-11440)
* Clomegestone acetate (clomagestone acetate; SH-741)
* Cymegesolate (megestrol acetate 3-cypionate; Progestin No. 1)
* Edogestrone (edogesterone; PH-218)
* Hydromadinone acetate (chloroacetoxyprogesterone; CAP; NSC-33170)
* Hydroxyprogesterone heptanoate benzilic acid hydrazone
* Medroxyprogesterone caproate
* Megestrol caproate
* Methenmadinone caproate (Lutofollin, in combination with estradiol valerate)

### Esters of 19-norprogesterone derivatives

#### Marketed

The following progestogen esters have been marketed:

* Gestonorone caproate (gestronol hexanoate; Depostat, Primostat)
* Nomegestrol acetate (Lutenyl, Naemis, Zoely)
* Segesterone acetate (Nestorone, Elcometrine)

And the following veterinary-only progestogen esters have also been marketed:

* Norgestomet (norgestamet; Syncro-Mate B; SC-21009)

#### Never marketed

* Amadinone acetate (19-norchlormadinone acetate; RS-2208)
* Gestadienol acetate (CIBA-31458-Ba, CIBA-31458)
* Gestonorone acetate
* 18-Methylsegesterone acetate (18-methylnestorone)
* Oxogestone phenpropionate (xinogestone)

## Esters of testosterone derivatives

### Esters of 19-nortestosterone derivatives

#### Marketed

The following progestogen esters have been marketed:

* Etynodiol diacetate (ethynodiol diacetate; Continuin, Femulen, Luteonorm, Luto-Metrodiol, Metrodiol)
* Norethisterone acetate (norethindrone acetate; Primolut-Nor, Norlestrin, Aygestin, Norlutate, Minovlar, Anovlar)
* Norethisterone enanthate (norethindrone enanthate; Noristerat, Norigest)
* Norgestimate (Ortho-Cyclen, Ortho Tri-Cyclen, Previfem, Sprintec, Prefest)
* Quingestanol acetate (Demovis, Pilomin, Riglovis, Unovis)

Many 19-nortestosterone androgen esters, such as nandrolone esters like nandrolone decanoate (Deca-Durabolin) and nandrolone phenpropionate (Durabolin), also have potent progestogenic activity.

#### Never marketed

* 6,6-Difluoronorethisterone acetate (6,6-difluoronorethindrone acetate)
* Levonorgestrel acetate (LNG-A)
* Levonorgestrel butanoate (LNG-B; HRP-002)
* Levonorgestrel cyclobutylcarboxylate (HRP-001)
* Levonorgestrel cyclopropylcarboxylate (HRP-003)
* Lynestrenol phenylpropionate
* Metynodiol diacetate (methynodiol diacetate; SC-19198)
* Norethisterone acetate oxime (norethindrone acetate oxime; ORF-5263, So-36)

## Other conjugates of progesterone derivatives

### Ethers of progesterone derivatives

#### Marketed

Although not esters, the following progestogen ethers have been marketed:

* Pentagestrone acetate (17α-acetoxyprogesterone 3-cyclopentyl enol ether; Gestovis, Gestovister)
* Quingestrone (progesterone 3-cyclopentyl enol ether; PCPE; Enol-Luteovis; W-3399)

#### Never marketed

* Pentagestrone (17α-hydroxyprogesterone 3-cyclopentyl enol ether)
* Progesterone 3-acetyl enol ether (progesterone acetate)

### Cyclic ketals of progesterone derivatives

#### Marketed

See also: Chemistry:List of corticosteroid cyclic ketals

Although not esters, the following progestogen cyclic ketals (cyclic acetals) have been marketed:

* Algestone acetonide (dihydroxyprogesterone acetonide; 16α,17α-isopropylidenedioxyprogesterone; W-3395)
* Algestone acetophenide (dihydroxyprogesterone acetophenide; DHPA; Neolutin, Droxone, Deladroxone, Decadroxone, Dexadroxate, Bovitrol)
* Proligestone (14α,17α-propylidenedioxyprogesterone; 14α,17α-dihydroxyprogesterone cyclic acetal with propionaldehyde; Corvinan, Delvosteron)

### Oximes of progesterone derivatives

#### Never marketed

Although not esters, the following progestogen oximes have not been marketed:

* EIDD-036 (progesterone 20-oxime; P4-20-O)
* EIDD-1723 (progesterone 20E-[O-[(phosphonooxy)methyl]oxime] sodium salt)
* P1-185 (progesterone 3-O-(L-valine)-E-oxime)
* Progesterone 3-oxime (P4-3-O)
* Progesterone carboxymethyloxime (progesterone 3-(O-carboxymethyl)oxime; P4-3-CMO)
* Progesterone dioxime (progesterone 3,20-dioxime; P4-3,20-DO)
* VOLT-02 (progesterone "conjugate"; chemical structure unreleased)

## Other conjugates of testosterone derivatives

### Oximes of 19-nortestosterone derivatives

#### Marketed

Although not esters, the following progestogen oximes have been marketed:

* Norelgestromin (17α-ethynyl-18-methyl-19-nortestosterone 3-oxime)
* Norgestimate (17α-ethynyl-18-methyl-19-nortestosterone 3-oxime 17β-acetate)

#### Never marketed

* Norethisterone acetate oxime (17α-ethynyl-19-nortestosterone 3-oxime 17β-acetate)

## See also

* List of progestogens
* List of androgen esters
* List of estrogen esters
* List of corticosteroid esters

## References

1. ↑ J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ.
2. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC.
3. ↑ "List of Progestins". https://www.drugs.com/drug-class/progestins.html.
4. ↑ Sweetman, Sean C., ed (2009). "Sex hormones and their modulators". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. ISBN 978-0-85369-840-1. https://www.medicinescomplete.com/mc/martindale/.
5. ↑ "Mometasone furoate is a less specific glucocorticoid than fluticasone propionate". European Respiratory Journal 20 (6): 1386–92. 2002. doi:10.1183/09031936.02.02472001. PMID 12503693.

* 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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