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About This Item
Empirical Formula (Hill Notation):
C35H38Cl2N8O4
CAS Number:
Molecular Weight:
705.63
NACRES:
NA.24
PubChem Substance ID:
UNSPSC Code:
41116107
MDL number:
grade
pharmaceutical primary standard
API family
itraconazole
manufacturer/tradename
EDQM
application(s)
pharmaceutical (small molecule)
format
neat
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
General description
This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.
Application
Itraconazole EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.
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.
Packaging
The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.
Other Notes
Sales restrictions may apply.
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signalword
Warning
Storage Class
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
hcodes
Hazard Classifications
Acute Tox. 4 Oral
wgk
WGK 1
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Zsombor K Nagy et al.
International journal of pharmaceutics, 480(1-2), 137-142 (2015-01-18)
High speed electrospinning (HSES), compatible with pharmaceutical industry, was used to demonstrate the viability of the preparation of drug-loaded polymer nanofibers with radically higher productivity than the known single-needle electrospinning (SNES) setup. Poorly water-soluble itraconazole (ITRA) was formulated with PVPVA64
Ritesh Agarwal et al.
Mycoses, 56(5), 559-570 (2013-03-19)
Patients with aspergilloma can be safely managed with supportive therapy in absence of massive haemoptysis. We hypothesised that chronic cavitary pulmonary aspergillosis (CCPA) could also be managed on similar grounds. The aim of this prospective, randomised controlled trial was to
C H W Koks et al.
Pharmacological research, 46(2), 195-201 (2002-09-11)
The clinical pharmacology of itraconazole is presented in relation to its use in the treatment of fluconazole-resistant oropharyngeal candidosis. The oral solution is a new formulation of itraconazole in which itraconazole is solubilised with the use of cyclodextrin. This formulation