Allyltestosterone

Allyltestosterone
Clinical data
Other names	17α-Allyltestosterone; 17α-Allylandrost-4-en-17β-ol-3-one
Identifiers
	IUPAC name (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	98169-58-5;
PubChem CID	22808244;
ChemSpider	58190189;
UNII	54HM6O0YGK;
CompTox Dashboard (EPA)	DTXSID601047829 ;
Chemical and physical data
Formula	C22H32O2
Molar mass	328.496 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@]2(O)CC=C;
	InChI 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, 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]

References

^ 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.
^ ^a ^b Ahluwalia 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.
^ 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.
^ 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.
^ 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.

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[JosephyRadt2013-1] 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.

[Ahluwalia2008-2] Ahluwalia 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.

[US4885289-3] 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.

[Zeelen1990-4] 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.

[BerginkLoonen1985-5] 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.

[Madjerekde_Visser1960-6] 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.

[McKinnonSquires2011-7] 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.

[ProgramResources2013-8] 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.

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Allyltestosterone

See also

References