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.

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

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-(phosphonooxy)methyloxime 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 derivativesedit

Oximes of 19-nortestosterone derivativesedit

Marketededit

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 marketededit

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

See alsoedit

• List of progestogens
• List of androgen esters
• List of estrogen esters
• List of corticosteroid esters

Referencesedit