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.[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]

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

Pirzada OL (June 2002). "Effect of megestrol caproate on the reproductive function of laboratory animals". Bulletin of Experimental Biology and Medicine. 133 (6): 574–576. doi:10.1023/A:1020233925626. PMID 12447469. S2CID 24115315.
Grinenko GS, Kadatskii GM, Korkhov VV, Boikova VV (1981). "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): 718–720. doi:10.1007/BF00765383. ISSN 0091-150X. S2CID 46676531.
Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 595, 664, 657. ISBN 978-1-4757-2085-3.
Grinenko GS, Popova EV, Korkhov VV, Lesik EA, Petrosyan MA, Topil'skaya NI (March 2000). "Synthesis and biological activity of 17α-acetoxy-3β-phenylpropionyloxy-6-methylpregna-4,6-dien-20-one". Pharmaceutical Chemistry Journal. 34 (3): 113–114. doi:10.1007/BF02524577. ISSN 1573-9031. S2CID 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 (1982). "Research activities in the field of oral contraceptives in the People's Republic of China". Acta Obstetricia et Gynecologica Scandinavica. Supplement. 105: 51–60. doi:10.3109/00016348209155319. PMID 6952745. S2CID 44858028.
Yang YC, Gu XG, Li SX (1982). "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". In Beier HM, Karlson P (eds.). Proteins and Steroids in Early Pregnancy. pp. 335–342. doi:10.1007/978-3-642-67890-5_22. ISBN 978-3-642-67892-9.

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[pmid12447469-1] Pirzada OL (June 2002). "Effect of megestrol caproate on the reproductive function of laboratory animals". Bulletin of Experimental Biology and Medicine. 133 (6): 574–576. doi:10.1023/A:1020233925626. PMID 12447469. S2CID 24115315.

[GrinenkoKadatskii1981-2] Grinenko GS, Kadatskii GM, Korkhov VV, Boikova VV (1981). "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): 718–720. doi:10.1007/BF00765383. ISSN 0091-150X. S2CID 46676531.

[Elks2014-3] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 595, 664, 657. ISBN 978-1-4757-2085-3.

[GrinenkoPopova2000-4] Grinenko GS, Popova EV, Korkhov VV, Lesik EA, Petrosyan MA, Topil'skaya NI (March 2000). "Synthesis and biological activity of 17α-acetoxy-3β-phenylpropionyloxy-6-methylpregna-4,6-dien-20-one". Pharmaceutical Chemistry Journal. 34 (3): 113–114. doi:10.1007/BF02524577. ISSN 1573-9031. S2CID 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].

[pmid6952745-5] De-Wei Z (1982). "Research activities in the field of oral contraceptives in the People's Republic of China". Acta Obstetricia et Gynecologica Scandinavica. Supplement. 105: 51–60. doi:10.3109/00016348209155319. PMID 6952745. S2CID 44858028.

[YangGu1982-6] Yang YC, Gu XG, Li SX (1982). "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". In Beier HM, Karlson P (eds.). Proteins and Steroids in Early Pregnancy. pp. 335–342. doi:10.1007/978-3-642-67890-5_22. ISBN 978-3-642-67892-9.