List of progestogen esters
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
[edit | edit source]Esters of 17α-hydroxyprogesterone derivatives
[edit | edit source]Marketed
[edit | edit source]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
[edit | edit source]- 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
[edit | edit source]Marketed
[edit | edit source]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
[edit | edit source]- 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
[edit | edit source]Esters of 19-nortestosterone derivatives
[edit | edit source]Marketed
[edit | edit source]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
[edit | edit source]- 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
[edit | edit source]Ethers of progesterone derivatives
[edit | edit source]Marketed
[edit | edit source]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
[edit | edit source]- Pentagestrone (17α-hydroxyprogesterone 3-cyclopentyl enol ether)
- Progesterone 3-acetyl enol ether (progesterone acetate)
Cyclic ketals of progesterone derivatives
[edit | edit source]Marketed
[edit | edit source]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
[edit | edit source]Never marketed
[edit | edit source]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
[edit | edit source]Oximes of 19-nortestosterone derivatives
[edit | edit source]Marketed
[edit | edit source]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
[edit | edit source]- Norethisterone acetate oxime (17α-ethynyl-19-nortestosterone 3-oxime 17β-acetate)
See also
[edit | edit source]References
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