List of progestogen esters

From Wikipedia, the free encyclopedia

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][5]

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:

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.[6]

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:

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[]

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.
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1.
  3. ^ "List of Progestins".
  4. ^ http://www.micromedexsolutions.com
  5. ^ 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.
  6. ^ Austin RJ, Maschera B, Walker A, Fairbairn L, Meldrum E, Farrow SN, Uings IJ (2002). "Mometasone furoate is a less specific glucocorticoid than fluticasone propionate". European Respiratory Journal. 20 (6): 1386–92. doi:10.1183/09031936.02.02472001. PMID 12503693.


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