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Documenti fondamentali

I6657

Sigma-Aldrich

Itraconazole

≥98% (HPLC)

Sinonimo/i:

Oriconazole, R51211, Sporanox

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About This Item

Formula empirica (notazione di Hill):
C35H38Cl2N8O4
Numero CAS:
Peso molecolare:
705.63
Numero MDL:
Codice UNSPSC:
51102829
ID PubChem:
NACRES:
NA.85

Saggio

≥98% (HPLC)

Colore

white

Solubilità

chloroform: 50 mg/mL, clear, colorless

Spettro attività antibiotica

fungi

Modalità d’azione

enzyme | inhibits

Temperatura di conservazione

2-8°C

Stringa SMILE

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
VHVPQPYKVGDNFY-UHFFFAOYSA-N

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Applicazioni

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.

Azioni biochim/fisiol

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.

Pittogrammi

Exclamation mark

Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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


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Katsuhisa Uchida et al.
The Journal of antimicrobial chemotherapy, 66(3), 626-634 (2010-12-22)
To examine whether in vitro antifungal susceptibility test results correlate with in vivo efficacy of two cyclodextrin-solubilized itraconazole formulations (intravenous and oral) against Candida in a murine model of invasive infection. A selected set of 12 Candida spp. strains with
Tomoya Sano et al.
Toxicologic pathology, 37(6), 790-798 (2009-08-25)
Alloxan-induced diabetic rats frequently exhibit proliferative lesions of squamous hyperplasia accompanied by chronic inflammation and Candida albicans infection in the forestomach, and some lesions progress to squamous cell carcinoma (SCC). Candida infection causes not only hyperplastic changes with inflammation but
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
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
M Blooi et al.
Scientific reports, 5, 11788-11788 (2015-07-01)
Chytridiomycosis caused by the chytrid fungus Batrachochytrium salamandrivorans (Bsal) poses a serious threat to urodelan diversity worldwide. Antimycotic treatment of this disease using protocols developed for the related fungus Batrachochytrium dendrobatidis (Bd), results in therapeutic failure. Here, we reveal that

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