Orteronel
6-[(7S)-7-hydroxy-5,6-dihydropyrrolo[1,2-c]imidazol-7-yl]-N-methylnaphthalene-2-carboxamide
Molecular Identity
Orteronel
6-[(7S)-7-hydroxy-5,6-dihydropyrrolo[1,2-c]imidazol-7-yl]-N-methylnaphthalene-2-carboxamide
PubChem CID: 9796590
Orteronel is a member of the class of pyrroloimidazoles that is 6,7-dihydro-5H-pyrrolo[1,2-c]imidazole substituted by hydroxy and 6-(methylcarbamoyl)naphthalen-2-yl groups at position 7 (the 7S-stereoisomer). It is a non-steroidal 17,20-lyase inhibitor that suppresses androgen synthesis. It was previously in clinical development for the treatment of castration-resistant prostate cancer trial now discontinued. It has a role as an antineoplastic agent, an EC 1.14.99.9 (steroid 17alpha-monooxygenase) inhibitor and a sterol biosynthesis inhibitor. It is a secondary carboxamide, a tertiary alcohol, a pyrroloimidazole and a naphthalenecarboxamide.
2D Structure
Properties
C18H17N3O2
Molecular Formula
307.30
Molecular Weight
g/mol
307.1321
Exact Mass
Da
1.3
XLogP
Drug-like (Lipinski: < 5)
67.2
TPSA
Good oral absorption (< 140 A²)
2
H-Bond Donors
3
H-Bond Acceptors
471
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Orteronel566939-85-3TAK-700orteronelumUE5K2FNS926-[(7S)-7-HYDROXY-6,7-DIHYDRO-5H-PYRROLO[1,2-C]IMIDAZOL-7-YL]-N-METHYL-2-NAPHTHALENECARBOXAMIDEDTXSID0013191216-((7S)-7-Hydroxy-6,7-dihydro-5H-pyrrolo(1,2-c)imidazol-7-yl)-N-methyl-2-naphthalenecarboxamide6-[(7S)-7-hydroxy-5H,6H,7H-pyrrolo[1,2-c]imidazol-7-yl]-N-methylnaphthalene-2-carboxamide6-((7S)-7-hydroxy-5H,6H,7H-pyrrolo(1,2-c)imidazol-7-yl)-N-methylnaphthalene-2-carboxamideRefChem:856930DTXCID101748551CYP17A1 Lyase Inhibitor TAK-700Androgen Synthesis Inhibitor TAK-700TAK 700
Data from PubChem (NCBI)
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