Megestrol caproate

Megestrol caproate

Clinical data
Other names	MGC; 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 class	Progestin; Progestogen; Progestogen ester
Identifiers
IUPAC name [(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	23265655
ChemSpider	10420418
Chemical and physical data
Formula	C28H40O4
Molar mass	440.624 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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

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

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. It is the C17α caproate (hexanoate) ester of megestrol. Closely related medications include megestrol acetate (MGA; megestrol 17α-acetate), acetomepregenol (megestrol 3β,17α-diacetate), and cymegesolate (megestrol 17α-acetate 3β-cypionate). In addition to MGA, analogues of MGC include chlormadinone caproate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone caproate, and methenmadinone caproate.