16-Methylene-17α-hydroxyprogesterone acetate
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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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Chemical and physical data | |
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
[edit]- ^ Kirk DN, Petrow V, Stansfield M, Williamson DM (1960). "481. Modified steroid hormones. Part XIV. 17α-Acetoxy-16-methylenepregn-4-ene-3,20-dione". Journal of the Chemical Society (Resumed): 2385–2388. doi:10.1039/JR9600002385. ISSN 0368-1769.
- ^ Mannhardt HJ, Werder FV, Bork KH, Metz H, Brückner K (1960). "Preparation of 16-methylene steroids of the corticoid and progesterone series". Tetrahedron Letters. 1 (16): 21–32. doi:10.1016/S0040-4039(01)99336-0. ISSN 0040-4039.
- ^ Syhora K (1961). "Steroid derivatives. IX. Partial synthesis of 17α-acetoxy-16-methyleneprogesterone". Collection of Czechoslovak Chemical Communications. 26: 1034–8. doi:10.1135/cccc19611034. ISSN 0010-0765.
- ^ Shapiro E, Legatt T, Weber L, Steinberg M, Watnick A, Eisler M, et al. (September 1962). "16-Alkylated Progesterones". Journal of Medicinal and Pharmaceutical Chemistry. 5 (5): 975–988. doi:10.1021/jm01240a010. PMID 14056440.
- ^ a b Čekan Z, Šeda M, Mikulášková J, Syhora K (1964). "Steroid derivatives XXXIV. On the progestational activity of 6-dehydro-16-methylene-17α-acetoxyprogesterone". Steroids. 4 (3): 415–421. doi:10.1016/0039-128X(64)90154-0. ISSN 0039-128X.
- ^ Milne GW (1 November 2017). Ashgate Handbook of Endocrine Agents and Steroids. Taylor & Francis. pp. 158–162. ISBN 978-1-351-74347-1.
- ^ Denkewalter RG, Tishler M, Ehrhart G, Biel JH, Lum BK, Büchi J, Winter CA, Münzel K, Kunz W, Ariëns EJ, Labhardt F (8 March 2013). Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques. Birkhäuser. pp. 407–. ISBN 978-3-0348-7059-7.