I7000000

Itraconazole

European Pharmacopoeia (EP) Reference Standard

Synonym(s):
Sporanox, R51211, Oriconazole
Empirical Formula (Hill Notation):
C35H38Cl2N8O4
CAS Number:
Molecular Weight:
705.63
MDL number:
PubChem Substance ID:
NACRES:
NA.24

grade

pharmaceutical primary standard

form

neat

manufacturer/tradename

EDQM

Featured Industry

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

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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.

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.

Packaging

Unit quantity: 20 mg. Subject to change. The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference subtance catalogue.

Caution

Other Notes

Sales restrictions may apply.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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...
A O S Fonseca et al.
The Journal of antimicrobial chemotherapy, 69(6), 1564-1567 (2014-02-14)
The purpose of this study was to compare the in vitro susceptibilities of 22 Brazilian isolates of Pythium insidiosum to antifungals using a standardized inoculum of zoospores and a proposed novel inoculum prepared from cultured mycelia (hyphae) of P. insidiosum....
Ji-Qin Wu et al.
Antimicrobial agents and chemotherapy, 58(8), 4464-4469 (2014-05-29)
Amphotericin B (AMB) has been a mainstay therapy for fungal infections of the central nervous system, but its use has been limited by its poor penetration into the brain, the mechanism of which remains unclear. In this study, we aimed...
Susan S Buchkowsky et al.
Therapeutic drug monitoring, 27(3), 322-333 (2005-05-21)
Itraconazole is a synthetic triazole antifungal agent that is commonly used in the prophylaxis and treatment of fungal infection. A role for itraconazole drug monitoring has been suggested previously; however, the advent of new formulations and increased clinical evidence may...
James D Homans et al.
The Pediatric infectious disease journal, 29(1), 65-67 (2009-11-04)
Coccidioides immitis causes a wide range of disease in humans. Fluconazole and itraconazole are effective treatments. Clinical evidence suggests that itraconazole is equivalent or superior to fluconazole in treating osteoarticular infections in rates of cure and recurrence. We report 2...

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