Chemistry:16-Methylene-17α-hydroxyprogesterone acetate
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Short description: Chemical compound
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| Other names | 16-Methylene-17α-acetoxyprogesterone; 16-Methylene-17α-acetoxypregn-4-en-3,20-dione |
| Drug class | Progestogen; Progestin; Progestogen ester |
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| Formula | C24H32O4 |
| Molar mass | 384.516 g·mol−1 |
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16-Methylene-17α-hydroxyprogesterone acetate is a progestin of the 17α-hydroxyprogesterone group which was never marketed.[1][2][3][4][5] Given orally, it shows about 2.5-fold the progestogenic activity of parenteral progesterone in animal bioassays.[5] It is a parent compound of the following clinically used progestins:[6][7]
- Chlormethenmadinone acetate (6-chloro-16-methylene-17α-hydroxy-Δ6-progesterone acetate)
- Melengestrol acetate (6-methyl-16-methylene-17α-hydroxy-Δ6-progesterone acetate)
- Methenmadinone acetate (16-methylene-17α-hydroxy-Δ6-progesterone acetate)
- Segesterone acetate (16-methylene-17α-hydroxy-19-norprogesterone acetate)
References
- ↑ "481. Modified steroid hormones. Part XIV. 17α-Acetoxy-16-methylenepregn-4-ene-3,20-dione". Journal of the Chemical Society (Resumed): 2385–2388. 1960. doi:10.1039/JR9600002385. ISSN 0368-1769.
- ↑ "Preparation of 16-methylene steroids of the corticoid and progesterone series". Tetrahedron Letters 1 (16): 21–32. 1960. doi:10.1016/S0040-4039(01)99336-0. ISSN 0040-4039.
- ↑ "Steroid derivatives. IX. Partial synthesis of 17α-acetoxy-16-methyleneprogesterone". Collection of Czechoslovak Chemical Communications 26: 1034–8. 1961. doi:10.1135/cccc19611034. ISSN 0010-0765.
- ↑ "16-Alkylated Progesterones". Journal of Medicinal and Pharmaceutical Chemistry 5 (5): 975–988. September 1962. doi:10.1021/jm01240a010. PMID 14056440.
- ↑ 5.0 5.1 "Steroid derivatives XXXIV. On the progestational activity of 6-dehydro-16-methylene-17α-acetoxyprogesterone". Steroids 4 (3): 415–421. 1964. doi:10.1016/0039-128X(64)90154-0. ISSN 0039-128X.
- ↑ Ashgate Handbook of Endocrine Agents and Steroids. Taylor & Francis. 1 November 2017. pp. 158–162. ISBN 978-1-351-74347-1. https://books.google.com/books?id=GFM8DwAAQBAJ&pg=PT158.
- ↑ Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Birkhäuser. 8 March 2013. pp. 407–. ISBN 978-3-0348-7059-7. https://books.google.com/books?id=ZSH3BwAAQBAJ&pg=PA407.
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