1354251

Itraconazole

United States Pharmacopeia (USP) Reference Standard

• Synonym(s): Oriconazole, R51211, Sporanox
• Empirical Formula (Hill Notation): C₃₅H₃₈Cl₂N₈O₄
• CAS Number: 84625-61-6
• Molecular Weight: 705.63
• MDL number: MFCD00870168
• UNSPSC Code: 41116107
• PubChem Substance ID: 329750213
• NACRES: NA.24

Properties

• grade: pharmaceutical primary standard
• API family: itraconazole
• manufacturer/tradename: USP
• application(s): pharmaceutical (small molecule)
• format: neat
• 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

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.

Application

Itraconazole USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:

• Itraconazole Capsules

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.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

Sales restrictions may apply.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302,H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P301 + P312 - P302 + P352 - P305 + P351 + P338
• 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