A metabolite of itraconazole
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Parent Compound(s)
13288Itraconazole
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Hydroxy Itraconazole

Item No. 22576

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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-(2-hydroxy-1-methylpropyl)-3H-1,2,4-triazol-3-one
CAS Number
112559-91-8
Synonyms
  • OH-ITZ
  • hydroxy-ITZ
Molecular Formula
C35H38Cl2N8O5
Formula Weight
721.6
Purity
≥95% (mixture of diastereomers)
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Acetonitrile:Methanol (1:1): Soluble
SMILES
O=C(N(C(C)C(O)C)N=C1)N1C(C=C2)=CC=C2N3CCN(C4=CC=C(OCC5OC(C6=C(Cl)C=C(Cl)C=C6)(CN7N=CN=C7)OC5)C=C4)CC3
InChi Code
InChI=1S/C35H38Cl2N8O5/c1-24(25(2)46)45-34(47)44(23-40-45)29-6-4-27(5-7-29)41-13-15-42(16-14-41)28-8-10-30(11-9-28)48-18-31-19-49-35(50-31,20-43-22-38-21-39-43)32-12-3-26(36)17-33(32)37/h3-12,17,21-25,31,46H,13-16,18-20H2,1-2H3
InChi Key
ISJVOEOJQLKSJU-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Hydroxy itraconazole (OH-ITZ) is an active metabolite of the antifungal agent itraconazole (Item No. 13288). Itraconazole is metabolized by the cytochrome P450 isoform 3A4 (CYP3A4) to form hydroxy itraconazole. Hydroxy itraconazole exhibits in vitro antifungal activity (MIC = 0.019, 0.078, and 0.078 mg/ml against C. albicans, A. fumigatus, and C. neoformans, respectively).1 Plasma concentration of hydroxy itraconazole is directly correlated to that of the parent compound and is used as an indicator of prophylaxis for fungal infections.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Mikami, Y., Sakamoto, T., Yazawa, K., et al. Comparison of in vitro antifungal activity of itraconazole and hydroxy-itraconazole by colorimetric MTT assay. Mycoses 37(1-2), 27-33 (1994).

    2. Mino, Y., Naito, T., Watanabe, T., et al. Hydroxy-itraconazole pharmacokinetics is similar to that of itraconazole in immunocompromised patients receiving oral solution of itraconazole. Clin. Chim. Acta. 415, 128-132 (2013).