Itraconazole
Itraconazole is a triazole antifungal that also exhibits anti-angiogenic and anticancer chemotherapeutic activities. Itraconazole inhibits synthesis of ergosterol, preventing fungal cell wall formation in Aspergillus. Itraconazole also inhibits hedgehog (Hh) signaling through activity on Smo, preventing growth of medulloblastoma tumors in vivo. Additionally, itraconazole inhibits VEGF-induced angiogenesis in other animal models. This compound also induces G1 phase cell cycle arrest in endothelial cells. Most of the biological activity of itraconazole is likely through the inhibition of 14-α demethylase.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18935945
| Cas No. |
84625-61-6 |
|---|---|
| Purity |
≥98% |
| Formula |
C35H38Cl2N8O4 |
| Formula Wt. |
705.63 |
| Chemical Name |
4-[4-[4-[4-[[2-(2,4-Dichlorophenyl)-2-(1H-1,2,4- triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]- phenyl]-1-peperazinyl]phenyl]-2,4-dihydro-2-(1- methylpropyl)-3H-1,2,4-triazol-3one |
| IUPAC Name |
2-butan-2-yl-4-[4-[4-[4-[[(2R,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 |
| Synonym |
Oriconazole; Itrizole; Sporanox; Triasporin |
| Melting Point |
166.2°C |
| Solubility |
Soluble in chloroform (50mg/mL). Practically insoluble in water and dilute acidic solutions. DMSO:4mg/mL |
| Appearance |
White or almost white powder |
Kim J, Tang JY, Gong R, et al. Itraconazole, a commonly used antifungal that inhibits Hedgehog pathway activity and cancer growth. Cancer Cell. 2010 Apr 13;17(4):388-99. PMID: 20385363.
Chong CR, Xu J, Lu J, et al. Inhibition of angiogenesis by the antifungal drug itraconazole. ACS Chem Biol. 2007 Apr 24;2(4):263-70. PMID: 17432820.
