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]

References

  1. ^ 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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ Milne GW (1 November 2017). Ashgate Handbook of Endocrine Agents and Steroids. Taylor & Francis. pp. 158–162. ISBN 978-1-351-74347-1.
  7. ^ 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.