Ethinylandrostenediol was first synthesized in the late 1930s and along with its close analogueethisterone (17α-ethynyltestosterone) was one of the first progestins (synthetic progestogens) to be developed.[7][8][9] Ethinylandrostenediol is orally active similarly to ethisterone and shows about half its progestogenic potency.[9] Ethinylandrostenediol was an intermediate in the initial synthesis of ethisterone.[10]
Ethinylandrostenediol shows tissue selectivity in its estrogenic effects in animals and doesn't seem to have estrogenic effects in the uterus.[1] The androgenic activity of ethinylandrostenediol is weak.[9]
Footnotes:a = (1) Binding affinity values are of the format "median (range)" (# (#–#)), "range" (#–#), or "value" (#) depending on the values available. The full sets of values within the ranges can be found in the Wiki code. (2) Binding affinities were determined via displacement studies in a variety of in-vitro systems with labeled estradiol and human ERα and ERβ proteins (except the ERβ values from Kuiper et al. (1997), which are rat ERβ). Sources: See template page.
^Beyler AL, Clinton RO (June 1956). "Uterine growth stimulating and testicular growth suppressing activities of 17alpha-ethinylandrostane-3beta, 17beta-diol, its delta 5-analog and derivatives". Proc. Soc. Exp. Biol. Med. 92 (2): 404–8. doi:10.3181/00379727-92-22493. PMID13350363. S2CID87469965.
^Masson G, Selye H (1945). "Additional steroids with luteoid activity". Journal of Pharmacology and Experimental Therapeutics. 84 (1): 46–52. JSTOR1671439.
^Overbeek GA (1948). "Luteoid activity of ethinyl-androstenediol". Acta Brevia Neerl Physiol Pharmacol Microbiol e A. 15 (5–7): 68. PMID18873577.
^Mardones E, Iglesias R, Lipschutz A (February 1956). "The antiluteinizing potency of five derivatives of progesterone". Endocrinology. 58 (2): 212–9. doi:10.1210/endo-58-2-212. PMID13285465.
^Neumann F (1968). "Chemische Konstitution und pharmakologische Wirkung". Die Gestagene. Handbuch der experimentellen Pharmakologie / Handbook of Experimental Pharmacology. Springer. pp. 680–1025. doi:10.1007/978-3-642-99941-3_6. ISBN978-3-642-99942-0.
^Stavely HE (1939). "Preparation of a Pregnane Compound from Dehydroandrosterone". Journal of the American Chemical Society. 61 (1): 79–80. doi:10.1021/ja01870a023. ISSN0002-7863.
^Stavely HE (1940). "The Preparation of Δ5-Pregnenediol-3,17-one-20 from Δ5-17-Ethynyl-androstenediol-3,17". Journal of the American Chemical Society. 62 (3): 489–491. doi:10.1021/ja01860a007. ISSN0002-7863.
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