Megestrol caproate

Megestrol caproate, abbreviated as MGC, is a progestin medication which was never marketed.[1][2] It was developed in Russia in 2002.[1] In animals, MGC shows 10-fold higher progestogenic activity compared to progesterone when both are administered via subcutaneous injection.[1] In addition, MGC has no androgenic, anabolic, or estrogenic activity.[1] The medication was suggested as a potential contraceptive and therapeutic agent.[1]

Megestrol caproate
Clinical data
Other namesMGC; Megestrol hexanoate; Megestrol 17α-caproate; 17α-Hydroxy-6-dehydro-6-methylprogesterone 17α-caproate; 17α-Hydroxy-6-methylpregna-4,6-diene-3,20-dione 17α-caproate
Drug classProgestin; Progestogen; Progestogen ester
Identifiers
  • [(8R,9S,10R,13S,14S,17R)-17-Acetyl-6,10,13-trimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] hexanoate
PubChem CID
ChemSpider
Chemical and physical data
FormulaC28H40O4
Molar mass440.624 g·mol−1
3D model (JSmol)
  • CCCCCC(=O)O[C@@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2C=C(C4=CC(=O)CC[C@]34C)C)C)C(=O)C
  • InChI=1S/C28H40O4/c1-6-7-8-9-25(31)32-28(19(3)29)15-12-23-21-16-18(2)24-17-20(30)10-13-26(24,4)22(21)11-14-27(23,28)5/h16-17,21-23H,6-15H2,1-5H3/t21-,22+,23+,26-,27+,28+/m1/s1
  • Key:XDVHIXRJLWUKRR-ORZTVLAMSA-N

Chemistry

Megestrol caproate, also known as megestrol 17α-caproate, as well as 17α-hydroxy-6-dehydro-6-methylprogesterone 17α-caproate or as 17α-hydroxy-6-methylpregna-4,6-diene-3,20-dione 17α-caproate, is a synthetic pregnane steroid and a derivative of progesterone and 17α-hydroxyprogesterone.[1][2] It is the C17α caproate (hexanoate) ester of megestrol.[1][2] Closely related medications include megestrol acetate (MGA; megestrol 17α-acetate), acetomepregenol (megestrol 3β,17α-diacetate), and cymegesolate (megestrol 17α-acetate 3β-cypionate).[3][4][5][6] In addition to MGA, analogues of MGC include chlormadinone caproate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone caproate, and methenmadinone caproate.

References