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I6657

Sigma-Aldrich

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
MDL number:
MFCD00870168
UNSPSC Code:
51102829
PubChem Substance ID:
329815394
NACRES:
NA.85

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

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Alexis Laurent et al.
Mycoses, 60(9), 581-586 (2017-05-10)
Trichophyton rubrum is the most frequently isolated dermatophyte species in European countries. The lack or poor sporulation of T. rubrum has always been a major complication and a limiting factor when performing antifungal susceptibility testing. Therefore, we describe an in vitro
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
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
Hanna Katarina Lilith Johansson et al.
Toxicological sciences : an official journal of the Society of Toxicology, 182(1), 60-69 (2021-04-28)
Early ovary development is considered to be largely hormone independent; yet, there are associations between fetal exposure to endocrine disrupting chemicals and reproductive disorders in women. This can potentially be explained by perturbations to establishment of ovarian endocrine function rather
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