Allyltestosterone

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Allyltestosterone
17a-allyltestosterone structure.png
Clinical data
Synonyms 17α-Allyltestosterone; 17α-Allylandrost-4-en-17β-ol-3-one
Identifiers
CAS Number
PubChem CID
ChemSpider
Chemical and physical data
Formula C22H32O2
Molar mass 328.4883 g/mol
3D model (JSmol)

Allyltestosterone, or 17α-allyltestosterone, also known as 17α-allylandrost-4-en-17β-ol-3-one, is a steroid derived from testosterone that was first synthesized in 1936 and was never marketed.[1][2] Along with propyltestosterone (topterone), it has been patented as a topical antiandrogen and hair growth inhibitor.[2][3] Allyltestosterone is the parent structure of two marketed 19-nortestosterone progestins, allylestrenol and altrenogest.[4] These progestins are unique among testosterone derivatives in that they appear to be associated with few or no androgenic effects.[5][6][7][8]

See also[edit]

References[edit]

  1. ^ Edith Josephy; F. Radt (1 December 2013). Elsevier’s Encyclopaedia of Organic Chemistry: Series III: Carboisocyclic Condensed Compounds. Springer. pp. 2653–. ISBN 978-3-662-25863-7. 
  2. ^ a b Gurpreet Ahluwalia (16 December 2008). Cosmetics Applications of Laser and Light-Based Systems. William Andrew. pp. 248–. ISBN 978-0-8155-1967-6. 
  3. ^ https://www.google.com/patents/US4885289
  4. ^ 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. 
  5. ^ 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. 
  6. ^ 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. 
  7. ^ Angus O. McKinnon; Edward L. Squires; Wendy E. Vaala; Dickson D. Varner (5 July 2011). Equine Reproduction. John Wiley & Sons. pp. 4462–. ISBN 978-0-470-96187-2. 
  8. ^ Committee to Review the Bureau of Land Management Wild Horse and Burro Management Program; Board on Agriculture and Natural Resources; Division on Earth and Life Studies; National Research Council (4 October 2013). Using Science to Improve the BLM Wild Horse and Burro Program: A Way Forward. National Academies Press. pp. 120–. ISBN 978-0-309-26494-5.