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I6657 Sigma-Aldrich

Itraconazole

≥98% (TLC)

Synonym: Oriconazole, R51211, Sporanox

  • CAS Number 84625-61-6

  • Empirical Formula (Hill Notation) C35H38Cl2N8O4

  • Molecular Weight 705.63

  •  MDL number MFCD00870168

  •  PubChem Substance ID 329815394

  •  NACRES NA.85

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics G-M, Antifungal, Biochemicals and Reagents,
Quality Level   200
assay   ≥98% (TLC)
color   white
solubility   chloroform: 50 mg/mL, clear, colorless
Mode of action   enzyme | inhibits
antibiotic activity spectrum   fungi
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

Description

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.

Packaging

100 mg in poly bottle

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.

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
XZ5481000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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