Chemistry:List of progestogen esters

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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:

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

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. https://books.google.com/books?id=0vXTBwAAQBAJ. 
  2. ↑ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC. 
  3. ↑ "List of Progestins". https://www.drugs.com/drug-class/progestins.html. 
  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. https://www.medicinescomplete.com/mc/martindale/. 
  6. ↑ "Mometasone furoate is a less specific glucocorticoid than fluticasone propionate". European Respiratory Journal 20 (6): 1386–92. 2002. doi:10.1183/09031936.02.02472001. PMID 12503693. 



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