Megestrol caproate explained

Iupac Name:	[(8''R'',9''S'',10''R'',13''S'',14''S'',17''R'')-17-Acetyl-6,10,13-trimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1''H''-cyclopenta[''a'']phenanthren-17-yl] hexanoate
Width:	250px
Class:	Progestin Progestogen; Progestogen ester
Pubchem:	23265655
Chemspiderid:	10420418
Synonyms:	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
C:	28
H:	40
O:	4
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
Stdinchi:	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
Stdinchikey:	XDVHIXRJLWUKRR-ORZTVLAMSA-N

Megestrol caproate, abbreviated as MGC, is a progestin medication which was never marketed.^[1] ^[2] 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).^[3] ^[4] ^[5] ^[6] In addition to MGA, analogues of MGC include chlormadinone caproate, gestonorone caproate, hydroxyprogesterone caproate, medroxyprogesterone caproate, and methenmadinone caproate.

Notes and References

Pirzada OL . Effect of megestrol caproate on the reproductive function of laboratory animals . Bulletin of Experimental Biology and Medicine . 133 . 6 . 574–576 . June 2002 . 12447469 . 10.1023/A:1020233925626 . 24115315 .
Grinenko GS, Kadatskii GM, Korkhov VV, Boikova VV . Preparation of 6-methylpregna-4,6-diene-3β,17α-diol-20-one 17-caproate and its influence on the reproductive function in rats . Pharmaceutical Chemistry Journal . 15 . 10 . 1981 . 718–720 . 0091-150X . 10.1007/BF00765383 . 46676531.
Book: Elks J . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. 14 November 2014. Springer. 978-1-4757-2085-3. 595, 664, 657.
Grinenko GS, Popova EV, Korkhov VV, Lesik EA, Petrosyan MA, Topil'skaya NI . Synthesis and biological activity of 17α-acetoxy-3β-phenylpropionyloxy-6-methylpregna-4,6-dien-20-one. Pharmaceutical Chemistry Journal. 1573-9031. 113–114. 34. 3. March 2000. 10.1007/BF02524577 . 44235508. Note that 3,17-diacetoxy-6-methylpregna-4,6-dien-20-one (1b), a structural analog of compound 1a, is certified in Russia under the trade name acetomepregnol and recommended for therapeutic purposes in gynecological practice and as a contraceptive preparation in combination with estrogens [4]..
De-Wei Z . Research activities in the field of oral contraceptives in the People's Republic of China . Acta Obstetricia et Gynecologica Scandinavica. Supplement . 105 . 51–60 . 1982 . 6952745 . 10.3109/00016348209155319 . 44858028 .
Book: Yang YC, Gu XG, Li SX . Antifertility Effect of a Long-Acting Progestin (3-Cyclopentyl Propionate of Megestrol Acetate): Prematurity of the Endometrium and Accompanying Changes of Uteroglobin and Progesterone in Uterine Fluid . Beier HM, Karlson P. Proteins and Steroids in Early Pregnancy . 1982. 335–342. 10.1007/978-3-642-67890-5_22. 978-3-642-67892-9.