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17α-Allyl-19-nortestosterone

17α-Allyl-19-nortestosterone
17α-Allyl-19-nortestosterone.svg
Clinical data
SynonymsAllylnortestosterone; Allylestrenolone; Allylnandrolone; 3-Ketoallylestrenol; 17α-Allylestr-4-en-17β-ol-3-one; Allylestrenolone
Drug classProgestogen
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
FormulaC21H30O2
Molar mass314.469 g/mol g·mol−1
3D model (JSmol)

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 PR AR ER GR MR SHBG CBG
Allylestrenol 0 0 0 0 ? 1 ?
17α-Allyl-19-NT 186 5 0 10 ? 3 ?
Values are percentages (%). Reference ligands (100%) were P4 for the PR, T for the AR, E2 for the ER, DEXA for the GR, aldosterone for the MR, T for SHBG, and cortisol for CBG.

See also

References

  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): 816–24. doi:10.1210/endo-63-6-816. PMID 13609555.
  3. ^ a b Dorfman RI (3 February 2016). 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.
  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): 165–8. doi:10.1016/0022-4731(85)90232-8. PMID 3928974.
  7. ^ Madjerek Z, de Visser J, van der Vies J, Overbeek GA (1960). "Allylestrenol, a Pregnancy Maintaining Oral Gestagen". European Journal of Endocrinology. XXXV (I): 8–19. doi:10.1530/acta.0.XXXV0008. ISSN 0804-4643.