17α-Methylprogesterone

17α-Methylprogesterone (17α-MP), or 17α-methylpregn-4-ene-3,20-dione, is a steroidal progestin related to progesterone that was synthesized and characterized in 1949 but was never marketed.

[1] Along with ethisterone (1938) and 19-norprogesterone (1951), 17α-MP was one of the earliest derivatives of progesterone to be identified as possessing progestogenic activity.

[2] Similarly to progesterone and derivatives like 17α-hydroxyprogesterone and 19-norprogesterone, 17α-MP was found to possess poor (though not negligible) oral bioavailability,[3] but showed improved progestogenic activity relative to progesterone when administered via other routes (e.g., subcutaneous or vaginal).

[5] Subsequently, hydroxyprogesterone acetate and hydroxyprogesterone caproate were synthesized in 1953 and introduced in 1956 and 1957, respectively, and medroxyprogesterone acetate was discovered in 1957 and introduced in 1959.

[5] In addition, though 17α-MP itself was never introduced for medical use, progestogen derivatives of the compound, including medrogestone (1966) and the 19-norprogesterone derivatives demegestone (1974), promegestone (1983), and trimegestone (2001), have been marketed.