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Hydroxy itraconazole

Product NameHydroxy itraconazole
CAS112559-91-8
MFC35H38Cl2N8O5
MW721.63
EINECS
MOL File112559-91-8.mol

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
Major Application	clinical testing
InChIKey	ISJVOEOJQLKSJU-UHFFFAOYSA-N
SMILES	Clc1c(ccc(c1)Cl)C3(OC(CO3)COc4ccc(cc4)N5CCN(CC5)c6ccc(cc6)N7C=NN(C7=O)C(C(O)C)C)C[n]2ncnc2

Safety Information

WGK Germany	WGK 1
Storage Class	3 - Flammable liquids
Hazard Classifications	Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Flam. Liq. 2 STOT SE 1

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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