Progestogen ester

A progestogen ester is an <a href="/facts/Ester/FoUAIIw4">ester</a> of a <a href="/facts/Progestogen/kodep35t">progestogen</a> or <a href="/facts/Progestin/8xMJYV3A">progestin</a> (a <a href="/facts/Synthetic_compound/gqCNaN45">synthetic</a> progestogen). The prototypical progestogen is <a href="/facts/Progesterone_(medication)/U3NtGBtS">progesterone</a>, an <a href="/facts/Endogenous/DFkSLkRI">endogenous</a> <a href="/facts/Sex_hormone/mI6bkHII">sex hormone</a>. Esterification is frequently employed to improve the <a href="/facts/Pharmacokinetics/x4CUUnle">pharmacokinetics</a> of <a href="/facts/Steroid/4AhMbgXt">steroids</a>, including <a href="/facts/Oral_administration/vNQcvLVx">oral</a> <a href="/facts/Bioavailability/9l6na9MV">bioavailability</a>, <a href="/facts/Lipophilicity/AWpsR8Xe">lipophilicity</a>, and <a href="/facts/Elimination_half-life/7nB2JtMr">elimination half-life</a>. In addition, with <a href="/facts/Intramuscular_injection/PPNwW2wB">intramuscular injection</a>, steroid esters are often absorbed more slowly into the body, allowing for less frequent administration. Many (though not all) steroid esters function as <a href="/facts/Prodrug/cg0GNhH0">prodrugs</a>.
Esterification is particularly salient in the case of progesterone because progesterone itself shows very poor oral pharmacokinetics and is thus ineffective when taken orally. Unmodified, it has an elimination half-life of only 5 minutes, and is almost completely inactivated by the <a href="/facts/Liver/Rtp4Fk2b">liver</a> during <a href="/facts/First-pass_metabolism/jfDsbq7S">first-pass metabolism</a>. <a href="/facts/Micronization/sk8jFE9I">Micronization</a>, however, has allowed for progesterone to be effective orally, although oral micronized progesterone was not developed until recent years.
Examples of important progestogen esters include the <a href="/facts/17%25CE%25B1-hydroxyprogesterone/RzVgaTaK">17α-hydroxyprogesterone</a> <a href="/facts/Chemical_derivative/JYcbLkbm">derivatives</a> <a href="/facts/Medroxyprogesterone_acetate/q6XACYYp">medroxyprogesterone acetate</a>, <a href="/facts/Megestrol_acetate/Gdybmob0">megestrol acetate</a>, <a href="/facts/Cyproterone_acetate/I9qdguIp">cyproterone acetate</a>, and <a href="/facts/Hydroxyprogesterone_caproate/rqTaBegr">hydroxyprogesterone caproate</a>, the <a href="/facts/19-norprogesterone/rtIt5Rpq">19-norprogesterone</a> derivative <a href="/facts/Nomegestrol_acetate/CKdb6Vlr">nomegestrol acetate</a>, and the <a href="/facts/19-nortestosterone/ezrNGa2U">19-nortestosterone</a> derivatives <a href="/facts/Norethisterone_acetate/M3NHp5Y8">norethisterone acetate</a> and <a href="/facts/Norethisterone_enanthate/GrwqPRsn">norethisterone enanthate</a>.

Progestogen ester open-in-new

Progestogen ester