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Oxabolone

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Chemical compound Pharmaceutical compound
Oxabolone
Clinical data
Other names4-Hydroxy-19-nortestosterone; 4,17β-Dihydroxyestr-4-en-3-one; 19-Norandrost-4-ene-4,17β-diol-3-one
Routes of
administration
Intramuscular injection (as oxabolone cipionate)
Drug classAndrogen; Anabolic steroid
Identifiers
IUPAC name
  • (8R,9S,10R,13S,14S,17S)-4,17-dihydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopentaphenanthren-3-one
CAS Number
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.022.920 Edit this at Wikidata
Chemical and physical data
FormulaC18H26O3
Molar mass290.403 g·mol
3D model (JSmol)
SMILES
  • O=C4CC3C(/CC13CC2(C)(O)CC12)=C4/O
InChI
  • InChI=1S/C18H26O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h10-12,14,16,20-21H,2-9H2,1H3/t10-,11-,12-,14+,16+,18+/m1/s1
  • Key:GXHBCWCMYVTJOW-YGRHGMIBSA-N

Oxabolone is a synthetic anabolic-androgenic steroid (AAS) of the nandrolone (19-nortestosterone) group which was never marketed. It can be formulated as the cipionate ester prodrug oxabolone cipionate, which, in contrast, has been marketed for medical use.

Oxabolone is on the World Anti-Doping Agency's list of prohibited substances, and is therefore banned from use in most major sports.

The 17α-methylated analogue of oxabolone is methylhydroxynandrolone (4-hydroxy-17α-methyl-19-nortestosterone) and the 17α- and 19-methylated derivative of oxabolone is oxymesterone (4-hydroxy-17α-methyltestosterone).

References

  1. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 908–. ISBN 978-1-4757-2085-3.
  2. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 765–. ISBN 978-3-88763-075-1.
  3. ^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 211–. ISBN 978-94-011-4439-1.
  4. "The World Anti-Doping Code: The 2012 Prohibited List" (PDF). World Anti-Doping Agency. Archived from the original (PDF) on 2012-05-13. Retrieved 2012-07-17.
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
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