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I6657

Itraconazole

≥98% (HPLC)

Synonym(s):

Oriconazole, R51211, Sporanox

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About This Item

Empirical Formula (Hill Notation):
C35H38Cl2N8O4
CAS Number:
84625-61-6
Molecular Weight:
705.63
NACRES:
NA.85
PubChem Substance ID:
329815394
UNSPSC Code:
51102829
MDL number:
MFCD00870168
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Quality Level

200

assay

≥98% (HPLC)

color

white

solubility

chloroform: 50 mg/mL, clear, colorless

antibiotic activity spectrum

fungi

mode of action

enzyme | inhibits

storage temp.

2-8°C

SMILES string

CCC(C)N1N=CN(C1=O)c2ccc(cc2)N3CCN(CC3)c4ccc(OCC5COC(Cn6cncn6)(O5)c7ccc(Cl)cc7Cl)cc4

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

InChI key

VHVPQPYKVGDNFY-UHFFFAOYSA-N

Application

Itraconazole is a triazole antifungal agent. It is used to inhibit cytochrome P-450-dependent enzymes and ergosterol synthesis. It has been used against histoplasmosis, blastomycosis, cryptococcal meningitis, and aspergillosis. It′s different formulations are used to study Candida strains in murine invasive infections. It has been used to study proliferative changes of the forestomach mucosa in alloxan-induced diabetic rats.

Biochem/physiol Actions

Itraconazole inhibits cytochrome P-450-dependent enzymes which results in the inhibition of ergosterol synthesis. It does so by interacting with 14-α demethylase, which is a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. Ergosterol is a crucial compenent of fungal cell membranes. Therefore, it′s inhibition results in increased cellular permeability causing leakage of cellular contents. Itraconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and phospholipid biosynthesis.
Synthetic broad-spectrum triazole antifungal agent. Mode of action: Inhibits cytochrome P450 dependent enzymes including 14α-demethylase. The inhibition results in prevention of the biosynthesis of ergosterol, a critical fungal cell wall component.

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pictograms

Exclamation mark
GHS07

signalword

Warning

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

wgk

WGK 1

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

I6657-100MG: + I6657-BULK: + I6657-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
097K1156
087K1322
114K0911
113K1501
102K0960

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