Chemistry:Megestrol caproate
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| 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 |
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| Chemical and physical data | |
| Formula | C28H40O4 |
| Molar mass | 440.624 g·mol−1 |
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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
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 "Effect of megestrol caproate on the reproductive function of laboratory animals". Bulletin of Experimental Biology and Medicine 133 (6): 574–576. June 2002. doi:10.1023/A:1020233925626. PMID 12447469.
- ↑ 2.0 2.1 2.2 "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. 1981. doi:10.1007/BF00765383. ISSN 0091-150X.
- ↑ The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 595,664,657. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA657.
- ↑ "Synthesis and biological activity of 17α-acetoxy-3β-phenylpropionyloxy-6-methylpregna-4,6-dien-20-one". Pharmaceutical Chemistry Journal 34 (3): 113–114. March 2000. 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].".
- ↑ "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. doi:10.3109/00016348209155319. PMID 6952745.
- ↑ "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". Proteins and Steroids in Early Pregnancy. 1982. pp. 335–342. doi:10.1007/978-3-642-67890-5_22. ISBN 978-3-642-67892-9.
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