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]
Quick Facts Clinical data, Other names ...
Allyltestosterone |
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Other names | 17α-Allyltestosterone; 17α-Allylandrost-4-en-17β-ol-3-one |
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(8R,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-17-prop-2-enyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
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Formula | C22H32O2 |
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Molar mass | 328.496 g·mol−1 |
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C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@]2(O)CC=C
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InChI=1S/C22H32O2/c1-4-10-22(24)13-9-19-17-6-5-15-14-16(23)7-11-20(15,2)18(17)8-12-21(19,22)3/h4,14,17-19,24H,1,5-13H2,2-3H3/t17-,18+,19+,20+,21+,22-/m1/s1 Key:DFRQHISHXQPKMU-VEYVBMQYSA-N
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US 4885289, Breuer MM, Kaszynski EG, Shander D, Usdin VR, van der Lee H, "Alteration of character of male beard growth", issued 5 December 1989, assigned to Gillette Co LLC.
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.
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.
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.
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). "Methods and Effects of Fertility Management". Using Science to Improve the BLM Wild Horse and Burro Program: A Way Forward. National Academies Press. pp. 93–142 (120). ISBN 978-0-309-26494-5.