17α-Allyl-19-nortestosterone: Difference between revisions
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| synonyms = 3-Ketoallylestrenol; 17α-Allylestr-4-en-17β-ol-3-one; Allylestrenolone |
| synonyms = Allylnortestosterone; Allylestrenolone; Allylnandrolone; 3-Ketoallylestrenol; 17α-Allylestr-4-en-17β-ol-3-one; Allylestrenolone |
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Revision as of 16:25, 24 December 2017
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| Other names | Allylnortestosterone; Allylestrenolone; Allylnandrolone; 3-Ketoallylestrenol; 17α-Allylestr-4-en-17β-ol-3-one; Allylestrenolone |
| Drug class | Progestogen |
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| Formula | C21H30O2 |
| Molar mass | 314.469 g/mol g·mol−1 |
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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.[1][2][3] It is a combined derivative of the anabolic–androgenic steroid nandrolone (19-nortestosterone) and the antiandrogen allyltestosterone (17α-allyltestosterone).[1][2][3] The drug is an active metabolite of allylestrenol, which is thought to be a prodrug of 17α-allyl-19-nortestosterone.[4][5]
References
- ^ a b Colton, Frank B.; Nysted, Leonard N.; Riegel, Byron; Raymond, Albert L (1957). "17-Alkyl-19-nortestosterones". Journal of the American Chemical Society. 79 (5): 1123–1127. doi:10.1021/ja01562a028. ISSN 0002-7863.
- ^ a b MIYAKE T, PINCUS G (1958). "Progestational activity of certain 19-norsteroids and progesterone derivatives". Endocrinology. 63 (6): 816–24. doi:10.1210/endo-63-6-816. PMID 13609555.
- ^ a b Ralph I. Dorfman (3 February 2016). Bioassay. Elsevier. pp. 134–. ISBN 978-1-4832-7276-4.
- ^ McRobb L, Handelsman DJ, Kazlauskas R, Wilkinson S, McLeod MD, Heather AK (2008). "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay". J. Steroid Biochem. Mol. Biol. 110 (1–2): 39–47. doi:10.1016/j.jsbmb.2007.10.008. PMID 18395441.
- ^ F. J. Zeelen (1990). Medicinal chemistry of steroids. Elsevier Science Limited. pp. 108–109. ISBN 978-0-444-88727-6.
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.