Oxendolone

From Infogalactic: the planetary knowledge core
Jump to: navigation, search
Oxendolone
Oxendolone.svg
Names
IUPAC name
(8R,9S,10R,13S,14S,16S,17S)-16-Ethyl-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
Systematic IUPAC name
(16β,17β)-16-Ethyl-17-hydroxyestr-4-en-3-one
Other names
Roxenone
Identifiers
33765-68-3
ChemSpider 392001
Jmol 3D model Interactive image
PubChem 443947
Properties
C20H30O2
Molar mass 302.46 g·mol−1
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Oxendolone (INN, USAN, JAN) (brand name Prostetin; former developmental code name TSAA-291), also known as 16β-ethyl-17β-hydroxy-4-estren-3-one, is a steroidal antiandrogen and progestin that has been marketed in Japan by Takeda for the treatment of benign prostatic hyperplasia (BPH) since 1981.[1][2][3][4] It binds to the androgen receptor (AR) (Ki = 320 nM) and progesterone receptor (Ki = 20 nM) and acts as a weak but clinically relevant inhibitor of 5α-reductase (IC50 = 1.4 μM).[5][6][7][8] The binding affinity of oxendolone for the AR is far lower than that of cyproterone acetate.[9] At the AR, oxendolone is not a silent antagonist but is rather predominantly antagonistic with weak agonistic activity;[6] for this reason, it has been described as a selective androgen receptor modulator.[10] The drug has antigonadotropic properties via its progestogenic actions.[11] Although oxendolone is approved for the treatment of BPH in Japan, concerns have been raised about its use for this condition due to poor efficacy seen in clinical trials.[4]

See also

References

  1. J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 914–. ISBN 978-1-4757-2085-3.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  2. William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 2935–. ISBN 978-0-8155-1856-3.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  3. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  4. 4.0 4.1 Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  5. Annual Reports in Medicinal Chemistry. Academic Press. 8 September 1989. pp. 199–. ISBN 978-0-08-058368-6.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  6. 6.0 6.1 Annual report of Shionogi Research Laboratories. 1991. pp. 76–77.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
  7. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  8. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  9. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  10. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).
  11. Lua error in Module:Citation/CS1/Identifiers at line 47: attempt to index field 'wikibase' (a nil value).