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Allyltestosterone

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Allyltestosterone
Clinical data
Other names17α-Allyltestosterone; 17α-Allylandrost-4-en-17β-ol-3-one
Identifiers
  • (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
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC22H32O2
Molar mass328.496 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@]2(O)CC=C
  • 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

Allyltestosterone, or17α-allyltestosterone, also known as17α-allylandrost-4-en-17β-ol-3-one, is asteroid derived fromtestosterone that was firstsynthesized in 1936 and was never marketed.[1][2] Along withpropyltestosterone (topterone), it has been patented as a topicalantiandrogen and hair growth inhibitor.[2][3] Allyltestosterone is theparent structure of two marketed19-nortestosteroneprogestins,allylestrenol andaltrenogest.[4] These progestins are unique among testosterone derivatives in that they appear to be associated with few or noandrogenic effects.[5][6][7][8]

See also

[edit]

References

[edit]
  1. ^Josephy E, Radt F (1 December 2013)."Allyltestosterone".Elsevier's Encyclopaedia of Organic Chemistry: Series III: Carboisocyclic Condensed Compounds. Springer. pp. 2653–.ISBN 978-3-662-25863-7.
  2. ^abAhluwalia GS (16 December 2008)."Management of unwanted hair". In Ahluwalia G (ed.).Cosmetics Applications of Laser and Light-Based Systems. William Andrew. pp. 239–252 (248).ISBN 978-0-8155-1967-6.
  3. ^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. 
  4. ^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.
  5. ^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.
  6. ^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.
  7. ^Bain FT (5 July 2011)."Infectious arthritis and osteomyelitis". In McKinnon AO, Squires EL, Vaala WE, Varner DD (eds.).Equine Reproduction. John Wiley & Sons. pp. 457–462.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)."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.
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists


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