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Names | |
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IUPAC name
6-(7-Hydroxy-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-7-yl)-N-methylnaphthalene-2-carboxamide
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Other names
TAK-700
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Identifiers | |
3D model (JSmol)
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ChEBI | |
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KEGG |
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PubChem CID
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UNII | |
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Properties | |
C18H17N3O2 | |
Molar mass | 307.353 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Orteronel (TAK-700) is a nonsteroidal CYP17A1 inhibitor 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.
ARTooltip Androgen receptor |
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GPRC6A |
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