Itraconazole

Itraconazole is an antifungal agent and inhibitor of hedgehog signaling (IC50 = 800 nM). It binds to 14-alpha sterol demethylase/CYP51 isoform B (AF51B, Kd = 31 nM for A. fumigatus enzyme expressed in E. coli) and inhibits ergosterol biosynthesis in C. neoformans (IC50 = 6 nM after a 16-hour incubation). It inhibits the growth of C. neoformans by 50% when used at a concentration of 3.2 nM. Itraconazole inhibits hedgehog signaling, reducing accumulation of Smoothened induced by sonic hedgehog (Shh) in primary cilia of NIHT-3T3 cells. It suppresses growth of medulloblastomas in a Ptch+/-p53-/- mouse allograft model when administered at a dose of 100 mg/kg twice daily. Itraconazole (1.25-100 µM) also reduces viral titers of several enteroviruses, including human rhinovirus 17, in infected cells, effects that can be reversed by overexpression of OSBP, the gene encoding oxysterol-binding protein (OSBP).Formal 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-piperazinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl)-3H-1,2,4-triazol-3-one. CAS Number: 84625-61-6. Molecular Formula: C35H38Cl2N8O4. Formula Weight: 705.6. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 0.5 mg/ml, DMSO: 0.5 mg/ml. lambdamax: 263 nm. SMILES: O=C(N(C(C)CC)N=C1)N1C(C=C2)=CC=C2N3CCN(C4=CC=C(OC[C@]5([H])O[C@](C6=C(Cl)C=C(Cl)C=C6)(CN7N=CN=C7)OC5)C=C4)CC3. InChi Code: InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m0/s1. InChi Key: VHVPQPYKVGDNFY-ZPGVKDDISA-N.