Itraconazole

Chemistry

Also known as

• 84625-61-6
• Oriconazole
• Sporanox
• Itraconazol
• Sporonox
• Fungitraxx
• Itraconazolo
• Onmel

Stereoisomers

8 distinct stereoisomers are registered for this structure. This area's record is the racemate — the mixture, which is normally the form encountered.

• Itraconazole, (R)-(-)- CID 9961741
• itraconazole, (S)-(+)- CID 14179008
• 2-[(2S)-butan-2-yl]-4-[4-[4-[4-[[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one CID 14179009
• 2-[(2R)-butan-2-yl]-4-[4-[4-[4-[[(2S,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one CID 14179010
• 4-(4-(4-(4-(((2R,4S)-2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl)-2,4-dihydro-2-((1S)-1-methylpropyl)-3H-1,2,4-triazol-3-one CID 14179013
• Itraconazole, (S)-(-)- CID 24867300
• Itraconazole EP Impurity E CID 56675666
• 2-[(2S)-butan-2-yl]-4-[4-[4-[4-[[(2R,4R)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one CID 56682298
• Itrizole mixture CID 3793

Attribution

• PJ

  Paul Janssen — first synthesis, 1984

  Janssen Pharmaceutica under his direction (code R 51 211), first described in 1984 with Janssen as senior author; chemistry from the Heeres/Backx group that made ketoconazole. Wikipedia's infobox gives a 1978 patent year, which does not fit the R-number or the literature — treat the date as approximate. Family name is invented.

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