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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 | name-list-style = vanc |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 | date = December 1958 | pmid = 13609555 | doi = 10.1210/endo-63-6-816 }}</ref><ref name="Dorfman2016">{{cite book| first = Ralph I. | last = Dorfman | name-list-style = vanc |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 = The Journal of Steroid Biochemistry and Molecular Biology | volume = 110 | issue = 1–2 | pages = 39–47 | date = May 2008 | pmid = 18395441 | doi = 10.1016/j.jsbmb.2007.10.008 | s2cid = 5612000 }}</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| vauthors = Zeelen FJ |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>
'''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| vauthors = Colton FB, Nysted LN, Riegel B, Raymond AL |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 = 816–824 | date = December 1958 | pmid = 13609555 | doi = 10.1210/endo-63-6-816 }}</ref><ref name="Dorfman2016">{{cite book| vauthors = Miyake T | chapter = Progestational Substances | veditors = Dorfman RI |title=Methods in Hormone Research | volume = 2 Bioassay | chapter-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 = The Journal of Steroid Biochemistry and Molecular Biology | volume = 110 | issue = 1–2 | pages = 39–47 | date = May 2008 | pmid = 18395441 | doi = 10.1016/j.jsbmb.2007.10.008 | s2cid = 5612000 }}</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| vauthors = Zeelen FJ |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>


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]], 2.8% of the affinity of testosterone for [[sex hormone-binding globulin]], and less than 0.2% of the affinity of [[estradiol (medication)|estradiol]] for the [[estrogen receptor]].<ref name="BerginkLoonen1985">{{cite journal | vauthors = Bergink EW, Loonen PB, Kloosterboer HJ | title = Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties | journal = Journal of Steroid Biochemistry | volume = 23 | issue = 2 | pages = 165–8 | date = August 1985 | pmid = 3928974 | doi = 10.1016/0022-4731(85)90232-8 }}</ref><ref name="Madjerekde Visser1960">{{cite journal | vauthors = Madjerek Z, de Visser J, van der Vies J, Overbeek GA | 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| pmid = 13765069}}</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" />
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]], 2.8% of the affinity of testosterone for [[sex hormone-binding globulin]], and less than 0.2% of the affinity of [[estradiol (medication)|estradiol]] for the [[estrogen receptor]].<ref name="BerginkLoonen1985">{{cite journal | vauthors = Bergink EW, Loonen PB, Kloosterboer HJ | title = Receptor binding of allylestrenol, a progestagen of the 19-nortestosterone series without androgenic properties | journal = Journal of Steroid Biochemistry | volume = 23 | issue = 2 | pages = 165–168 | date = August 1985 | pmid = 3928974 | doi = 10.1016/0022-4731(85)90232-8 }}</ref><ref name="Madjerekde Visser1960">{{cite journal | vauthors = Madjerek Z, De Visser J, Van Der Vies J, Overbeek GA | title = Allylestrenol, a pregnancy maintaining oral gestagen | journal = Acta Endocrinologica | volume = 35 | issue = I | pages = 8–19 | date = September 1960 | pmid = 13765069 | 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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Latest revision as of 08:37, 12 August 2023

17α-Allyl-19-nortestosterone
Clinical data
Other namesAllylnortestosterone; Allylestrenolone; Allylnandrolone; 3-Ketoallylestrenol; 17α-Allylestr-4-en-17β-ol-3-one; Allylestrenolone
Drug classProgestogen
Identifiers
  • (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
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(CC=C)O)CCC4=CC(=O)CC[C@H]34
  • InChI=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
  • Key: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.[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, 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.[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]

Relative affinities (%) of allylestrenol and metabolites[6]
Compound PRTooltip Progesterone receptor ARTooltip Androgen receptor ERTooltip Estrogen receptor GRTooltip Glucocorticoid receptor MRTooltip Mineralocorticoid receptor SHBGTooltip Sex hormone-binding globulin CBGTooltip Corticosteroid binding globulin
Allylestrenol 0 0 0 0 ? 1 ?
17α-Allyl-19-NT 186 5 0 10 ? 3 ?
Values are percentages (%). Reference ligands (100%) were P4Tooltip progesterone (medication) for the PRTooltip progesterone receptor, TTooltip testosterone (medication) for the ARTooltip androgen receptor, E2 for the ERTooltip estrogen receptor, DEXATooltip dexamethasone for the GRTooltip glucocorticoid receptor, aldosterone for the MRTooltip mineralocorticoid receptor, TTooltip testosterone (medication) for SHBGTooltip sex hormone-binding globulin, and cortisol for CBGTooltip Corticosteroid-binding globulin.

See also

[edit]

References

[edit]
  1. ^ a b Colton FB, Nysted LN, Riegel B, Raymond AL (1957). "17-Alkyl-19-nortestosterones". Journal of the American Chemical Society. 79 (5): 1123–1127. doi:10.1021/ja01562a028. ISSN 0002-7863.
  2. ^ a b Miyake T, Pincus G (December 1958). "Progestational activity of certain 19-norsteroids and progesterone derivatives". Endocrinology. 63 (6): 816–824. doi:10.1210/endo-63-6-816. PMID 13609555.
  3. ^ a b Miyake T (3 February 2016). "Progestational Substances". In Dorfman RI (ed.). Methods in Hormone Research. Vol. 2 Bioassay. Elsevier. pp. 134–. ISBN 978-1-4832-7276-4.
  4. ^ a b McRobb L, Handelsman DJ, Kazlauskas R, Wilkinson S, McLeod MD, Heather AK (May 2008). "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. doi:10.1016/j.jsbmb.2007.10.008. PMID 18395441. S2CID 5612000.
  5. ^ Zeelen FJ (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.
  6. ^ a b c d Bergink EW, Loonen PB, Kloosterboer HJ (August 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. PMID 3928974.
  7. ^ Madjerek Z, De Visser J, Van Der Vies J, Overbeek GA (September 1960). "Allylestrenol, a pregnancy maintaining oral gestagen". Acta Endocrinologica. 35 (I): 8–19. doi:10.1530/acta.0.XXXV0008. PMID 13765069.
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