Norethisterone acetate , a widely used progestogen ester andprodrug ofnorethisterone .Medroxyprogesterone acetate , a progestogen ester thatdoes not act as a prodrug.This is alist ofprogestogen esters , oresters ofprogestogens .[ 1] [ 2] [ 3] [ 4]
Unlike the case oftestosterone andestradiol ,progesterone cannot be esterified as it lackshydroxyl groups , so all progestogen esters, with the exception of esters of17α-hydroxyprogesterone likehydroxyprogesterone caproate , are esters ofprogestins (synthetic progestogens) and are non-bioidentical . In addition, whereas allandrogen andestrogen esters areprodrugs of theparent compound , only some and not all progestogen esters act asprodrugs . Esters of 17α-hydroxyprogesterone and19-norprogesterone derivatives like hydroxyprogesterone caproate,medroxyprogesterone acetate , andnomegestrol acetate are active themselves andare not prodrugs, whereas esters of19-nortestosterone derivatives likenorethisterone acetate andnorethisterone enanthate are not active themselves andare prodrugs.
Esters of progesterone derivatives [ edit ] [ edit ] The following major progestogen esters have been marketed:
And the following minor progestogen esters have been marketed:
The followingveterinary -only progestogen esters have also been marketed:
Thecorticosteroid ester mometasone furoate (Asmanex, Elocom, Elocon, Elosalic, Nasonex), which is a 17α-hydroxyprogesterone derivative, also has verypotent progestogenic activity, though it is not used as a progestogen and is instead used exclusively as a corticosteroid.[ 5]
Esters of 19-norprogesterone derivatives [ edit ] The following progestogen esters have been marketed:
And the following veterinary-only progestogen esters have also been marketed:
Esters of testosterone derivatives [ edit ] Esters of 19-nortestosterone derivatives [ edit ] 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-nortestosteroneandrogen esters , such asnandrolone esters likenandrolone decanoate (Deca-Durabolin) andnandrolone phenpropionate (Durabolin), also have potent progestogenic activity.
Other conjugates of progesterone derivatives [ edit ] Ethers of progesterone derivatives [ edit ] Although not esters, the following progestogenethers
Pentagestrone acetate (17α-acetoxyprogesterone 3-cyclopentyl enol ether; Gestovis, Gestovister)Quingestrone (progesterone 3-cyclopentyl enol ether; PCPE; Enol-Luteovis; W-3399)Cyclic ketals of progesterone derivatives [ edit ] Although not esters, the following progestogencyclic ketals 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 ] Although not esters, the following progestogenoximes
Other conjugates of testosterone derivatives [ edit ] Oximes of 19-nortestosterone derivatives [ edit ] Although not esters, the following progestogenoximes
Norelgestromin (17α-ethynyl-18-methyl-19-nortestosterone 3-oxime)Norgestimate (17α-ethynyl-18-methyl-19-nortestosterone 3-oxime 17β-acetate)
PR Tooltip Progesterone receptor
Agonists Testosterone derivatives: Progestins:6,6-Difluoronorethisterone 6,6-Difluoronorethisterone acetate 17α-Allyl-19-nortestosterone Allylestrenol Altrenogest Chloroethynylnorgestrel Cingestol Danazol Desogestrel Dienogest Ethinylandrostenediol 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 MixedSPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor PAQR Tooltip Progestin and adipoQ receptor )
