17α-Allyl-19-nortestosterone

Chemical compound (8R,9S,10R,13S,14S,17R)-17-hydroxy-13-methyl-17-prop-2-enyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one 17α-Allyl-19-nortestosterone.svg skin-invert-image 225px Progestogen correct CAS 7358-46-5 22790929 22270 correct FDA EH9MJ5WS79 Allylnortestosterone; Allylestrenolone; Allylnandrolone; 3-Ketoallylestrenol; 17α-Allylestr-4-en-17β-ol-3-one; Allylestrenolone 21 30 2 C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(CC=C)O)CCC4=CC(=O)CC[C@H]34 1S/C21H30O2/c1-3-10-21(23)12-9-19-18-6-4-14-13-15(22)5-7-16(14)17(18)8-11-20(19,21)2/h3,13,16-19,23H,1,4-12H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1 NXGWVXNWOIYZLE-XUDSTZEESA-N 17α-Allyl-19-nortestosterone, also known as 3-ketoallylestrenol or as 17α-allylestr-4-en-17β-ol-3-one, is a progestin which was never marketed. Colton FB, Nysted LN, Riegel B, Raymond AL 17-Alkyl-19-nortestosterones Journal of the American Chemical Society 79 5 1957 1123–1127 0002-7863 10.1021/ja01562a028 1957JAChS..79.1123C Miyake T, Pincus G Progestational activity of certain 19-norsteroids and progesterone derivatives Endocrinology 63 6 816–824 December 1958 13609555 10.1210/endo-63-6-816 Miyake T Progestational Substances Dorfman RI Methods in Hormone Research 2 Bioassay https://books.google.com/books?id=WS_LBAAAQBAJ&pg=PA134 3 February 2016 Elsevier 978-1-4832-7276-4 134– McRobb L, Handelsman DJ, Kazlauskas R, Wilkinson S, McLeod MD, Heather AK Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay The Journal of Steroid Biochemistry and Molecular Biology 110 1–2 39–47 May 2008 18395441 10.1016/j.jsbmb.2007.10.008 5612000 It is a combined derivative of the anabolic–androgenic steroid and progestogen nandrolone (19-nortestosterone) and the antiandrogen allyltestosterone (17α-allyltestosterone). The drug is a major active metabolite of allylestrenol, which is thought to be a prodrug of 17α-allyl-19-nortestosterone. Zeelen FJ Medicinal chemistry of steroids https://books.google.com/books?id=px9tAAAAMAAJ 1990 Elsevier Science Limited 978-0-444-88727-6 108–109 Other examples are allylestrenol (42), a pro-drug converted to the 3-keto analogue (43), which is used in the treatment of threatened abortion [78,79] and altrenogest (44), used in sows and mares to suppress ovulation and estrus behaviour [80]. [...] Progestins with a 17a-allyl side chain: (42) allylestrenol, (43), (44) altrenogest. 17α-Allyl-19-nortestosterone has 24% of the affinity of ORG-2058 and 186% of the affinity of progesterone for the progesterone receptor, 4.5% of the affinity of testosterone for the androgen receptor, 9.8% of the affinity of dexamethasone for the glucocorticoid receptor, 2.8% of the affinity of testosterone for sex hormone-binding globulin, and less than 0.2% of the affinity of estradiol for the estrogen receptor. Bergink EW, Loonen PB, Kloosterboer HJ Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties Journal of Steroid Biochemistry 23 2 165–168 August 1985 3928974 10.1016/0022-4731(85)90232-8 Madjerek Z, De Visser J, Van Der Vies J, Overbeek GA Allylestrenol, a pregnancy maintaining oral gestagen Acta Endocrinologica 35 I 8–19 September 1960 13765069 10.1530/acta.0.XXXV0008 The affinity of 17α-allyl-19-nortestosterone for the androgen receptor was less than that of norethisterone and medroxyprogesterone acetate and its affinity for sex hormone-binding globulin was much lower than that of norethisterone. These findings may help to explain the absence of teratogenic effects of allylestrenol on the external genitalia of female and male rat fetuses. Relative affinities (%) of allylestrenol and metabolites Compound PR Progesterone receptor AR Androgen receptor ER Estrogen receptor GR Glucocorticoid receptor MR Mineralocorticoid receptor SHBG Sex hormone-binding globulin CBG Corticosteroid binding globulin Allylestrenol 0 0 0 0 ? 1 ? 17α-Allyl-19-NT 17α-Allyl-19-nortestosterone 186 5 0 10 ? 3 ? Values are percentages (%). Reference ligands (100%) were P4 progesterone (medication) for the PR progesterone receptor, T testosterone (medication) for the AR androgen receptor, E2 estradiol for the ER estrogen receptor, DEXA dexamethasone for the GR glucocorticoid receptor, aldosterone for the MR mineralocorticoid receptor, T testosterone (medication) for SHBG sex hormone-binding globulin, and cortisol for CBG Corticosteroid-binding globulin. See also Altrenogest Ethinyltestosterone Vinyltestosterone References Category:Abandoned drugs Category:Tertiary alcohols Category:Allyl compounds Category:Estranes Category:Human drug metabolites Category:Enones Category:Progestogens