17α-Allyl-19-nortestosterone: Difference between revisions
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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.<ref name="ColtonNysted1957">{{cite journal|last1=Colton|first1=Frank B.|last2=Nysted|first2=Leonard N.|last3=Riegel|first3=Byron|last4=Raymond|first4=Albert L|title=17-Alkyl-19-nortestosterones|journal=Journal of the American Chemical Society|volume=79|issue=5|year=1957|pages=1123–1127|issn=0002-7863|doi=10.1021/ja01562a028}}</ref><ref name="pmid13609555">{{cite journal | vauthors = |
'''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.<ref name="ColtonNysted1957">{{cite journal|last1=Colton|first1=Frank B.|last2=Nysted|first2=Leonard N.|last3=Riegel|first3=Byron|last4=Raymond|first4=Albert L|title=17-Alkyl-19-nortestosterones|journal=Journal of the American Chemical Society|volume=79|issue=5|year=1957|pages=1123–1127|issn=0002-7863|doi=10.1021/ja01562a028}}</ref><ref name="pmid13609555">{{cite journal | vauthors = Miyake T, Pincus G | title = Progestational activity of certain 19-norsteroids and progesterone derivatives | journal = Endocrinology | volume = 63 | issue = 6 | pages = 816–24 | year = 1958 | pmid = 13609555 | doi = 10.1210/endo-63-6-816 | url = }}</ref><ref name="Dorfman2016">{{cite book|author=Ralph I. Dorfman|title=Bioassay|url=https://books.google.com/books?id=WS_LBAAAQBAJ&pg=PA134|date=3 February 2016|publisher=Elsevier|isbn=978-1-4832-7276-4|pages=134–}}</ref><ref name="pmid18395441">{{cite journal | vauthors = McRobb L, Handelsman DJ, Kazlauskas R, Wilkinson S, McLeod MD, Heather AK | title = Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay | journal = J. Steroid Biochem. Mol. Biol. | volume = 110 | issue = 1-2 | pages = 39–47 | year = 2008 | pmid = 18395441 | doi = 10.1016/j.jsbmb.2007.10.008 | url = }}</ref> It is a combined [[chemical derivative|derivative]] of the [[anabolic–androgenic steroid]] and [[progestogen]] [[nandrolone]] (19-nortestosterone) and the [[antiandrogen]] [[allyltestosterone]] (17α-allyltestosterone).<ref name="ColtonNysted1957" /><ref name="pmid13609555" /><ref name="Dorfman2016" /> The drug is a major [[active metabolite]] of [[allylestrenol]], which is thought to be a [[prodrug]] of 17α-allyl-19-nortestosterone.<ref name="pmid18395441" /><ref name="Zeelen1990">{{cite book|author=F. J. Zeelen|title=Medicinal chemistry of steroids|url=https://books.google.com/books?id=px9tAAAAMAAJ|year=1990|publisher=Elsevier Science Limited|isbn=978-0-444-88727-6|pages=108–109|quote=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.}}</ref> |
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17α-Allyl-19-nortestosterone has 24% of the [[affinity (pharmacology)|affinity]] of [[ORG-2058]] and 186% of the affinity of [[progesterone (medication)|progesterone]] for the [[progesterone receptor]], 4.5% of the affinity of [[testosterone (medication)|testosterone]] for the [[androgen receptor]], 9.8% of the affinity of [[dexamethasone]] for the [[glucocorticoid receptor]], and 2.8% of the affinity of testosterone for [[sex hormone-binding globulin]], while it similarly has less than 0.2% of the affinity of [[estradiol (medication)|estradiol]] for the [[estrogen receptor]].<ref name="BerginkLoonen1985">{{cite journal|last1=Bergink|first1=E.W.|last2=Loonen|first2=P.B.A.|last3=Kloosterboer|first3=H.J.|title=Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties|journal=Journal of Steroid Biochemistry|volume=23|issue=2|year=1985|pages=165–168|issn=0022-4731|doi=10.1016/0022-4731(85)90232-8|pmid=3928974}}</ref><ref name="Madjerekde Visser1960">{{cite journal|last1=Madjerek|first1=Z.|last2=de Visser|first2=J.|last3=van der Vies|first3=J.|last4=Overbeek|first4=G. A.|title=Allylestrenol, a Pregnancy Maintaining Oral Gestagen|journal=European Journal of Endocrinology|volume=XXXV|issue=I|year=1960|pages=8–19|issn=0804-4643|doi=10.1530/acta.0.XXXV0008}}</ref> 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.<ref name="BerginkLoonen1985" /> These findings may help to explain the absence of [[teratogen]]ic effects of allylestrenol on the [[external genitalia]] of female and male rat [[fetus]]es.<ref name="BerginkLoonen1985" /> |
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==See also== |
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Revision as of 23:08, 10 March 2018
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| Clinical data | |
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| Other names | Allylnortestosterone; Allylestrenolone; Allylnandrolone; 3-Ketoallylestrenol; 17α-Allylestr-4-en-17β-ol-3-one; Allylestrenolone |
| Drug class | Progestogen |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| ChemSpider | |
| Chemical and physical data | |
| Formula | C21H30O2 |
| Molar mass | 314.469 g/mol g·mol−1 |
| 3D model (JSmol) | |
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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][4] It is a combined derivative of the anabolic–androgenic steroid and progestogen nandrolone (19-nortestosterone) and the antiandrogen allyltestosterone (17α-allyltestosterone).[1][2][3] The drug is a major active metabolite of allylestrenol, which is thought to be a prodrug of 17α-allyl-19-nortestosterone.[4][5]
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, and 2.8% of the affinity of testosterone for sex hormone-binding globulin, while it similarly has less than 0.2% of the affinity of estradiol for the estrogen receptor.[6][7] 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.[6] These findings may help to explain the absence of teratogenic effects of allylestrenol on the external genitalia of female and male rat fetuses.[6]
See also
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.
- ^ a b 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.
- ^ a b c Bergink, E.W.; Loonen, P.B.A.; Kloosterboer, H.J. (1985). "Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties". Journal of Steroid Biochemistry. 23 (2): 165–168. doi:10.1016/0022-4731(85)90232-8. ISSN 0022-4731. PMID 3928974.
- ^ Madjerek, Z.; de Visser, J.; van der Vies, J.; Overbeek, G. A. (1960). "Allylestrenol, a Pregnancy Maintaining Oral Gestagen". European Journal of Endocrinology. XXXV (I): 8–19. doi:10.1530/acta.0.XXXV0008. ISSN 0804-4643.