16-Methylene-17α-hydroxyprogesterone acetate

Chemical compound [(8R,9S,10R,13S,14S,17R)-17-Acetyl-10,13-dimethyl-16-methylidene-3-oxo-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-17-yl] acetate 16-Methylene-17α-hydroxyprogesterone acetate.svg skin-invert-image 250px Progestogen; Progestin; Progestogen ester 6815-51-6 correct FDA XYO20AWR0I 151431 133463 16-Methylene-17α-acetoxyprogesterone; 16-Methylene-17α-acetoxypregn-4-en-3,20-dione 24 32 4 CC(=O)[C@]1(C(=C)C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)OC(=O)C 1S/C24H32O4/c1-14-12-21-19-7-6-17-13-18(27)8-10-22(17,4)20(19)9-11-23(21,5)24(14,15(2)25)28-16(3)26/h13,19-21H,1,6-12H2,2-5H3/t19-,20+,21+,22+,23+,24+/m1/s1 XSNMCQGNVPSIQM-CKOZHMEPSA-N 16-Methylene-17α-hydroxyprogesterone acetate is a progestin of the 17α-hydroxyprogesterone group which was never marketed. Kirk DN, Petrow V, Stansfield M, Williamson DM 481. Modified steroid hormones. Part XIV. 17α-Acetoxy-16-methylenepregn-4-ene-3,20-dione Journal of the Chemical Society (Resumed) 1960 2385–2388 0368-1769 10.1039/JR9600002385 Mannhardt HJ, Werder FV, Bork KH, Metz H, Brückner K Preparation of 16-methylene steroids of the corticoid and progesterone series Tetrahedron Letters 16 21–32 1960 1 10.1016/S0040-4039(01)99336-0 0040-4039 Syhora K Steroid derivatives. IX. Partial synthesis of 17α-acetoxy-16-methyleneprogesterone Collection of Czechoslovak Chemical Communications 26 1034–8 1961 0010-0765 10.1135/cccc19611034 Shapiro E, Legatt T, Weber L, Steinberg M, Watnick A, Eisler M, Hennessey MG, Coniglio CT, Charney W, Oliveto EP 6 16-Alkylated Progesterones Journal of Medicinal and Pharmaceutical Chemistry 5 5 975–988 September 1962 14056440 10.1021/jm01240a010 Čekan Z, Šeda M, Mikulášková J, Syhora K Steroid derivatives XXXIV. On the progestational activity of 6-dehydro-16-methylene-17α-acetoxyprogesterone Steroids 4 3 1964 415–421 0039-128X 10.1016/0039-128X(64)90154-0 Given orally, it shows about 2.5-fold the progestogenic activity of parenteral progesterone in animal bioassays. It is a parent compound of the following clinically used progestins: Milne GW Ashgate Handbook of Endocrine Agents and Steroids https://books.google.com/books?id=GFM8DwAAQBAJ&pg=PT158 1 November 2017 Taylor & Francis 978-1-351-74347-1 158–162 Denkewalter RG, Tishler M, Ehrhart G, Biel JH, Lum BK, Büchi J, Winter CA, Münzel K, Kunz W, Ariëns EJ, Labhardt F vanc Fortschritte der Arzneimittelforschung / Progress in Drug Research / Progrès des recherches pharmaceutiques https://books.google.com/books?id=ZSH3BwAAQBAJ&pg=PA407 8 March 2013 Birkhäuser 978-3-0348-7059-7 407– 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 Category:Abandoned drugs Category:Acetate esters Category:Diketones Category:Pregnanes Category:Progestogens Category:Vinylidene compounds