154003-19-7

Basic information

• Product Name: 3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[(2S,4R)-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-[ (1R)-1-methylpropyl]-
• CAS NO: 154003-19-7
• Molecular Formula: C35H38Cl2N8O4
• Molecular Weight: 705.644
• Mol File: 154003-19-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[(2S,4R)-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-[ (1R)-1-methylpropyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[(2S,4R)-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-[ (1R)-1-methylpropyl]-(154003-19-7)
• EPA Substance Registry System: 3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[(2S,4R)-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-[ (1R)-1-methylpropyl]-(154003-19-7)

Safety Data

• Hazardous Substances Data: 154003-19-7(Hazardous Substances Data)

Upstream product

• 58905-16-1 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethanone 
• 172587-60-9 (-)-(2S,cis)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolane-4-methanol 
• 67914-84-5 cis-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolane-4-methanol benzoate (ester) 
• 84604-65-9 itraconazole 
• 125235-74-7 (R)-2-(sec-butyl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one 
• 154003-21-1 ((2S,4S)-2-((1H-1,2,4-triazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methyl 4-methyl-benzenesulfonate 

Relevant articles and documents

Stereoselective determination of the epimer mixtures of itraconazole in human blood plasma using HPLC and fluorescence detection

Itraconazole is an antifungal drug widely used in a variety of fungal infections, which have become a significant public-health problem in recent decades. Itraconazole is a chiral drug consisting of two diastereoisomeric racemates, i.e., four stereoisomers. Data in the literature suggests that stereochemistry may play a significant role in the action and disposition of the drug and therefore stereoselective analytical methods for the determination of the drug in biological fluids are needed for the elucidation of that role. We report a stereoselective HPLC method that incorporates solvent extraction, the use of an internal standard, two chiral stationary phases in series, and fluorescence detection. The procedure is enantioselective and partially diastereoselective and provides the concentrations in blood plasma of the two epimer mixtures 2R,4S,2'R/2R,4S2'S and 2S,4R,2'R/2S,4R,2'S, respectively, each of which is a combination of the two epimers that differ in the configuration at the sec-butyl group. The analytical method has suitable sensitivity, recovery, precision, and accuracy. Analysis of the plasma of a human subject six hours after the oral administration of a single 200-mg dose of itraconazole showed a 3.4-fold difference between the concentrations of the epimer mixtures. The method has certain advantages over the published alternative procedure that uses LC-MS. Copyright

Impact of absolute stereochemistry on the antiangiogenic and antifungal activities of itraconazole

Itraconazole is used clinically as an antifungal agent and has recently been shown to possess antiangiogenic acitivity. Itraconazole has three chiral centers that give rise to eight stereoisomers. The complete role of stereochemistry in the two activities of itraconazole, however, has not been addressed adequately. For the first time, all eight stereoisomers of itraconazole (1a?h) have been synthesized and evaluated for activity against human endothelial cell proliferation and for antifungal activity against five fungal strains. Distinct antiangiogenic and antifungal activity profiles of the trans stereoisomers, especially 1e and 1f, suggest different molecular mechanisms underlying the antiangiogenic and antifungal activities of itraconazole.