17α-Methylprogesterone
Chemical compound / From Wikipedia, the free encyclopedia
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).[4][5][6] In addition to its activity as a progestogen, 17α-MP has also been found to possess some antiglucocorticoid activity.[7]
Clinical data | |
---|---|
Other names | 17α-MP; 17α-Methylpregn-4-ene-3,20-dione |
Drug class | Progestin; Progestogen |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
ChemSpider | |
UNII | |
CompTox Dashboard (EPA) | |
Chemical and physical data | |
Formula | C22H32O2 |
Molar mass | 328.496 g·mol−1 |
3D model (JSmol) | |
| |
|
The observation of two-fold improved potency of 17α-MP relative to progesterone led to renewed interest in 17α-substituted derivatives of progesterone.[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.[8]