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I6657

Sigma-Aldrich

Itraconazole

≥98% (HPLC)

Synonym(s):

Oriconazole, R51211, Sporanox

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5 G
CN¥152.62
100 G
CN¥211.74
500 G
CN¥308.48

CN¥152.62

Available to ship onApril 27, 2025Details

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5 G
CN¥152.62
100 G
CN¥211.74
500 G
CN¥308.48

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

CN¥152.62

Available to ship onApril 27, 2025Details

Request a Bulk Order

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

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Show Differences

1 of 4

This Item
603864106631T36609
p-Toluic acid 98%

T36803

p-Toluic acid

p-Toluic acid-α-13C 99 atom % 13C

603864

p-Toluic acid-α-13C

p-Toluoyl chloride 98%

106631

p-Toluoyl chloride

m-Toluic acid ReagentPlus®, 99%

T36609

m-Toluic acid

assay

98%

assay

-

assay

98%

assay

99%

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

100

bp

274-275 °C (lit.)

bp

274-275 °C

bp

225-227 °C (lit.), 95-96 °C/10 mmHg (lit.)

bp

263 °C (lit.)

mp

177-180 °C (lit.)

mp

177-180 °C

mp

−4-−2 °C (lit.)

mp

107-113 °C (lit.)

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[1]. It has been used to study proliferative changes of the forestomach mucosa in alloxan-induced diabetic rats[2].

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.

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
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    Lot/Batch Number
    WXBF2980V
    WXBF1079V
    MKCT5442
    WXBD8642V
    MKCM8261

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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
    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
    View All Related Papers

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