Orteronel

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Orteronel
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Names
IUPAC name
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methylnaphthalene-2-carboxamide
Other names
TAK-700
Identifiers
566939-85-3 YesY
ChEMBL ChEMBL1921976
ChemSpider 8058704
Jmol 3D model Interactive image
KEGG D10146 YesY
PubChem 9883029
UNII UE5K2FNS92
Properties
C18H17N3O2
Molar mass 307.35 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

Orteronel (TAK-700) is a non-steroidal antiandrogen that was being developed for the treatment of cancer by Takeda Pharmaceutical Company in conjunction with Millennium Pharmaceuticals.[1] It completed two phase III clinical trials for metastatic, hormone-refractory prostate cancer but failed to extend overall survival rates, and development was voluntarily terminated as a result.[2]

Orteronel is an androgen biosynthesis inhibitor. It selectively inhibits the enzyme CYP17A1[3] which is expressed in testicular, adrenal, and prostatic tumor tissues. CYP17 catalyzes two sequential reactions: (a) the conversion of pregnenolone and progesterone to their 17α-hydroxy derivatives by its 17α-hydroxylase activity, and (b) the subsequent formation of dehydroepiandrosterone (DHEA) and androstenedione, respectively, by its 17,20-lyase activity.[4] DHEA and androstenedione are androgens and precursors of testosterone. Inhibition of CYP17 activity thus decreases circulating levels of testosterone.

See also

References

  1. Millennium and Takeda Announce Advancement of Prostate Cancer Program, Millennium Pharmaceuticals
  2. MarketWatch (2014). "Takeda Announces Termination of Orteronel (TAK-700) Development for Prostate Cancer in Japan, U.S.A. and Europe".<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles>
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