Oxendolone

Not to be confused with Oxandrolone.
Oxendolone
Clinical data
Trade namesProstetin, Roxenone
Other namesTSAA-291; 16β-Ethyl-19-nortestosterone; 16β-Ethylestr-4-en-17β-ol-3-one
Routes of
administration		Intramuscular injection[1][2][3][4]
Drug classSteroidal antiandrogen; Progestogen; Progestin
Pharmacokinetic data
BioavailabilityOral: Very low (1% in dogs)[5]
Elimination half-lifeIMTooltip Intramuscular injection: 5.0–6.6 days.[4][6]
Identifiers
  • (9S,14S,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
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC20H30O2
Molar mass302.458 g·mol−1
3D model (JSmol)
  • CCC1CC2C3CCC4=CC(=O)CCC4C3CCC2(C1O)C
  • InChI=1S/C20H30O2/c1-3-12-11-18-17-6-4-13-10-14(21)5-7-15(13)16(17)8-9-20(18,2)19(12)22/h10,12,15-19,22H,3-9,11H2,1-2H3/t12?,15?,16-,17?,18+,19+,20?/m1/s1
  • Key:FCKLFGKATYPJPG-LNRSQMQGSA-N

Oxendolone, sold under the brand names Prostetin and Roxenone, is an antiandrogen and progestin medication which is used in Japan in the treatment of enlarged prostate.[7][8][9][10][11] However, this use is controversial due to concerns about its clinical efficacy.[11] Oxendolone is not effective by mouth and must be given by injection into muscle.[5][1][2][3][4]

Oxendolone is an antiandrogen, and hence is an antagonist of the androgen receptor, the biological target of androgens like testosterone and dihydrotestosterone.[12][13][14][15][6] It is also a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[12][13][14][15] Due to its progestogenic activity, oxendolone has antigonadotropic effects.[16][17] Oxendolone has no other important hormonal activity...

Oxendolone was introduced for medical use in 1981.[8] It is used only in Japan.[8][11]

  1. ^ a b Cite error: The named reference pmid6131442 was invoked but never defined (see the help page).
  2. ^ a b Cite error: The named reference pmid26335395 was invoked but never defined (see the help page).
  3. ^ a b Cite error: The named reference pmid2466359 was invoked but never defined (see the help page).
  4. ^ a b c Cite error: The named reference pmid6419414 was invoked but never defined (see the help page).
  5. ^ a b Cite error: The named reference RathboneHadgraft2002 was invoked but never defined (see the help page).
  6. ^ a b Gao W, Bohl CE, Dalton JT (September 2005). "Chemistry and structural biology of androgen receptor". Chemical Reviews. 105 (9): 3352–3370. doi:10.1021/cr020456u. PMC 2096617. PMID 16159155.
  7. ^ Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 914–. ISBN 978-1-4757-2085-3.
  8. ^ a b c William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. Elsevier. pp. 2935–. ISBN 978-0-8155-1856-3.
  9. ^ Negwer M, Scharnow HG (2001). Organic-chemical drugs and their synonyms: (an international survey). Wiley-VCH. p. 2023. ISBN 978-3-527-30247-5.
  10. ^ Tan MH, Li J, Xu HE, Melcher K, Yong EL (January 2015). "Androgen receptor: structure, role in prostate cancer and drug discovery". Acta Pharmacologica Sinica. 36 (1): 3–23. doi:10.1038/aps.2014.18. PMC 4571323. PMID 24909511.
  11. ^ a b c Ishizuka O, Nishizawa O, Hirao Y, Ohshima S (November 2002). "Evidence-based meta-analysis of pharmacotherapy for benign prostatic hypertrophy". International Journal of Urology. 9 (11): 607–612. doi:10.1046/j.1442-2042.2002.00539.x. PMID 12534901.
  12. ^ a b Cite error: The named reference AcademicPress1989 was invoked but never defined (see the help page).
  13. ^ a b Cite error: The named reference Shinogi1991 was invoked but never defined (see the help page).
  14. ^ a b Cite error: The named reference KirbyChristmas1991 was invoked but never defined (see the help page).
  15. ^ a b Cite error: The named reference BashirelahiGanesan1986 was invoked but never defined (see the help page).
  16. ^ Cite error: The named reference SudoYamazaki1979 was invoked but never defined (see the help page).
  17. ^ Cite error: The named reference pmid2435122 was invoked but never defined (see the help page).