Megestrol caproate

Megestrol caproate
Clinical data
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
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
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

1 2 3 4 5 6 7 Pirzada OL (June 2002). "Effect of megestrol caproate on the reproductive function of laboratory animals" (PDF). Bull. Exp. Biol. Med. 133 (6): 574–6. doi:10.1023/A:1020233925626. PMID 12447469.
1 2 3 Grinenko, G. S.; Kadatskii, G. M.; Korkhov, V. V.; Boikova, V. V. (1981). "Preparation of 6-methylpregna-4,6-diene-3?,17?-diol-20-one 17-caproate and its influence on the reproductive function in rats" (PDF). Pharmaceutical Chemistry Journal. 15 (10): 718–720. doi:10.1007/BF00765383. ISSN 0091-150X.
↑ J. Elks (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, G. S.; Popova, E. V.; Korkhov, V. V.; Lesik, E. A.; Petrosyan, M. A.; Topil'skaya, N. I. (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. 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 Obstet Gynecol Scand Suppl. 105: 51–60. PMID 6952745.
↑ Yang, Yi-chien; Gu, Xi-gen; Li, Shu-xiang (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": 335–342. doi:10.1007/978-3-642-67890-5_22.

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[pmid12447469-1] 1 2 3 4 5 6 7 Pirzada OL (June 2002). "Effect of megestrol caproate on the reproductive function of laboratory animals" (PDF). Bull. Exp. Biol. Med. 133 (6): 574–6. doi:10.1023/A:1020233925626. PMID 12447469.

[GrinenkoKadatskii1981-2] 1 2 3 Grinenko, G. S.; Kadatskii, G. M.; Korkhov, V. V.; Boikova, V. V. (1981). "Preparation of 6-methylpregna-4,6-diene-3?,17?-diol-20-one 17-caproate and its influence on the reproductive function in rats" (PDF). Pharmaceutical Chemistry Journal. 15 (10): 718–720. doi:10.1007/BF00765383. ISSN 0091-150X.

[Elks2014-3] J. Elks (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, G. S.; Popova, E. V.; Korkhov, V. V.; Lesik, E. A.; Petrosyan, M. A.; Topil'skaya, N. I. (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. 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 Obstet Gynecol Scand Suppl. 105: 51–60. PMID 6952745.

[YangGu1982-6] Yang, Yi-chien; Gu, Xi-gen; Li, Shu-xiang (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": 335–342. doi:10.1007/978-3-642-67890-5_22.