Orteronel

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]

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Orteronel

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
CAS Number	566939-85-3 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:231353
ChEMBL	ChEMBL1921976
ChemSpider	8058704
KEGG	D10146 Y
PubChem CID	9883029
UNII	UE5K2FNS92
InChI InChI=1S/C18H17N3O2/c1-19-17(22)14-3-2-13-9-15(5-4-12(13)8-14)18(23)6-7-21-11-20-10-16(18)21/h2-5,8-11,23H,6-7H2,1H3,(H,19,22)
SMILES O=C(NC)c2ccc1cc(ccc1c2)C4(O)c3cncn3CC4
Properties
Chemical formula	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). Infobox references

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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.