Misplaced Pages

Allyltestosterone

Article snapshot taken from Wikipedia with creative commons attribution-sharealike license. Give it a read and then ask your questions in the chat. We can research this topic together.
(Redirected from 17α-allyltestosterone) Chemical compound Pharmaceutical compound
Allyltestosterone
Clinical data
Other names17α-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-cyclopentaphenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H32O2
Molar mass328.496 g·mol
3D model (JSmol)
SMILES
  • C12CC3(CCC4=CC(=O)CC34C)1CC2(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. Along with propyltestosterone (topterone), it has been patented as a topical antiandrogen and hair growth inhibitor. Allyltestosterone is the parent structure of two marketed 19-nortestosterone progestins, allylestrenol and altrenogest. These progestins are unique among testosterone derivatives in that they appear to be associated with few or no androgenic effects.

See also

References

  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. ^ 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.
  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 and altrenogest (44), used in sows and mares to suppress ovulation and estrus behaviour . 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.
Androgen receptor modulators
ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens and anabolic steroids


Stub icon

This article about a steroid is a stub. You can help Misplaced Pages by expanding it.

Categories: