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HYDROXY ITRACONAZOLE

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HYDROXY ITRACONAZOLE Basic information

Product Name:
HYDROXY ITRACONAZOLE
Synonyms:
  • HYDROXY ITRACONAZOLE
  • 3H-1,2,4-Triazol-3-one, 4-4-4-4-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-ylmethoxyphenyl-1-piperazinylphenyl-2,4-dihydro-2-(2-hydroxy-1-methylpropyl)-
  • 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
  • R 63373
  • Itraconazole Impurity 8(Hydroxy Itraconazole)
  • 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)-
  • Itraconazole 2-Hydroxy Metabolite
  • Itraconazole metabolite Hydroxy Itraconazole
CAS:
112559-91-8
MF:
C35H38Cl2N8O5
MW:
721.63
Product Categories:
  • Intermediates & Fine Chemicals
  • Metabolites & Impurities
  • Pharmaceuticals
  • Various Metabolites and Impurities
  • Isotooe labelled metabolites
  • metabolites
  • Isotopically Labeled Pharmaceutical Reference Standard
Mol File:
112559-91-8.mol
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HYDROXY ITRACONAZOLE Chemical Properties

Melting point:
76-78°C
Boiling point:
884.7±75.0 °C(Predicted)
Density 
1.44±0.1 g/cm3(Predicted)
storage temp. 
-20°C Freezer
solubility 
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
form 
Solid
pka
14.72±0.20(Predicted)
color 
White to Pale Beige
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HYDROXY ITRACONAZOLE Usage And Synthesis

Description

Hydroxy itraconazole (OH-ITZ) is an active metabolite of the antifungal agent itraconazole . 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). 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.

Chemical Properties

Off-White Crystalline Solid

Uses

A metabolite of Itraconazole, an orally active antimycotic structurally related to Ketoconazole. It is a COVID19-related research product.

in vivo

The plasma concentration of Hydroxy Itraconazole is weakly dependent on the dose of ITZ, most likely because the process that forms Hydroxy Itraconazole is saturated. Serum albumin and GFR may alter the pharmacokinetics of ITZ and Hydroxy Itraconazole. Antifungal activity should be discussed while taking into account not only the plasma concentration of ITZ but also that of Hydroxy Itraconazole. However, the pharmacokinetics of Hydroxy Itraconazole is similar to that of ITZ in immunocompromised patients taking an oral solution of ITZ. Since the plasma concentrations of ITZ and Hydroxy Itraconazole are closely correlated, determining the plasma concentration of either should be sufficient from a clinical point of view[1].

References

[1] Y MIKAMI. Comparison of in vitro antifungal activity of itraconazole and hydroxy-itraconazole by colorimetric MTT assay.[J]. Mycoses, 1994, 37 1-2: 27-33. DOI: 10.1111/j.1439-0507.1994.tb00281.x
[2] YASUAKI MINO . Hydroxy-itraconazole pharmacokinetics is similar to that of itraconazole in immunocompromised patients receiving oral solution of itraconazole[J]. Clinica Chimica Acta, 2013, 415: Pages 128-132. DOI: 10.1016/j.cca.2012.10.028

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