List of progestogen esters explained
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:
And the following minor progestogen esters have been marketed:
The following veterinary-only progestogen esters have also been marketed:
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
Esters of 19-norprogesterone derivatives
Marketed
The following progestogen esters have been marketed:
And the following veterinary-only progestogen esters have also been marketed:
Never marketed
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
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
Cyclic ketals of progesterone derivatives
Marketed
See also: 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:
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
See also
Notes and References
- Book: J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3.
- Book: Index Nominum 2000: International Drug Directory. January 2000. Taylor & Francis. 978-3-88763-075-1.
- Web site: List of Progestins.
- Book: Sweetman, Sean C. . Sex hormones and their modulators . Martindale: The Complete Drug Reference . 36th . 2009 . Pharmaceutical Press . London. 978-0-85369-840-1.
- Austin RJ, Maschera B, Walker A, Fairbairn L, Meldrum E, Farrow SN, Uings IJ . Mometasone furoate is a less specific glucocorticoid than fluticasone propionate . European Respiratory Journal . 20 . 6 . 1386–92 . 2002 . 12503693 . 10.1183/09031936.02.02472001. free .