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    InvivoChem Cat #: V0805
    CAS #: 84625-61-6Purity ≥98%

    Description: Itraconazole (Orungal, Oriconazole, Sporanox, R51211; R-51211), a marketed triazole-based antifungal drug since 1984, is a potent inhibitor of CYP3A4 that has been widely used for the treatment of fungal infections. 

    References: Drug Metab Dispos. 2004 Oct;32(10):1121-31; Cancer Cell. 2010 Apr 13;17(4):388-99.

    Related CAS: 112559-91-8 (Hydroxy Itraconazole; R-63373);112560-33-5 (Keto-itraconazole, a metabolite of Itraconazole)

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    • 香港大学
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    Molecular Weight (MW)705.65
    CAS No.84625-61-6
    Storage-20℃ for 3 years in powder form
    -80℃ for 2 years in solvent
    Solubility (In vitro)DMSO: 7 mg/mL (9.9 mM)
    Water: <1 mg/mL
    Ethanol: <1 mg/mL
    Solubility (In vivo)5% DMSO+70% PEG 300+ddH2O: 9mg/mL
    SynonymsR51211, Orungal, Oriconazole, Sporanox, R 51211; R-51211, Itraconazole, Itraconazolum, Itraconazol, Itrizole 

    Chemical 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


    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

    SMILES Code: O=C1N(C(CC)C)N=CN1C2=CC=C(N3CCN(C4=CC=C(OC[[email protected]@H]5O[[email protected]@](CN6N=CN=C6)(C7=CC=C(Cl)C=C7Cl)OC5)C=C4)CC3)C=C2

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    In Vitro

    In vitro activity: Itraconazole is metabolized into hydroxy-itraconazole (OH-ITZ), a known in vivo metabolite of ITZ, and two new metabolites: keto-itraconazole (keto-ITZ) and N-desalkyl-itraconazole (ND-ITZ). Itraconazole is a substrate for CYP3A in vitro and to characterize the metabolites generated. Itraconazole exhibits an unbound Km of 3.9 nM for CYP3A. Itraconazole metabolites are as potent as or more potent CYP3A4 inhibitors than ITZ itself. Itraconazole appears to act on the essential Hh pathway component Smoothened (SMO) by a mechanism distinct from that of cyclopamine and other known SMO antagonists, and prevents the ciliary accumulation of SMO normally caused by Hh stimulation. Itraconazole is active against 60 clinical isolates of Aspergillus spp. with geometric mean (GM) MICs of 0.25 mg/mL. Itraconazole acts primarily by impairing the synthesis of ergosterol, resulting in a defective fungal cell membrane with altered permeability and function. Itraconazole is effective for a wide variety of mycotic infections and some fungal meningeal infections. Itraconazole has an affinity for mammalian cytochrome P-450 enzymes as well as for fungal P-450-dependent enzyme, and thus has the potential for clinically important interactions (e.g., astemizole, terfenadine, rifampin, oral contraceptives, H2 receptor antagonists, warfarin, cyclosporine).

    In VivoItraconazole, like other Hh pathway antagonists, can suppress Hh pathway activity and the growth of medulloblastoma in a mouse allograft model; Oral Administration of itraconazole (200 mg) once daily for 4 days increased the area under the midazolam concentration-time curve from 10 to 15 times (p < 0.001) and mean peak concentrations three to four times (p < 0.001) compared with the placebo phase
    Animal modelMouse
    Formulation & DosageOral Administration
    ReferencesDrug Metab Dispos. 2004 Oct;32(10):1121-31; Cancer Cell. 2010 Apr 13;17(4):388-99.

    These protocols are for reference only. InvivoChem does not independently validate these methods.


    Inhibition of Hh signaling by itraconazole is not mediated by effects on cholesterol biosynthesis. Cancer Cell. 2010 Apr 13;17(4):388-99


    Mapping of itraconazole action within the Hh pathway. Cancer Cell. 2010 Apr 13;17(4):388-99


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