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1354251 USP

Itraconazole

United States Pharmacopeia (USP) Reference Standard

Synonym: Oriconazole, R51211, Sporanox

  • CAS Number 84625-61-6

  • Empirical Formula (Hill Notation) C35H38Cl2N8O4

  • Molecular Weight 705.63

  •  MDL number MFCD00870168

  •  PubChem Substance ID 329750213

  •  NACRES NA.24

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Properties

Related Categories Analytical Standards, Analytical/Chromatography, Pharmacopeia & Metrological Institutes Standards, USP Standards, USP Standards I - K More...
Featured Industry   Pharmaceutical (small molecule)
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.

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

USP issued SDS can be found here.

Sales restrictions may apply.

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport

Documents

Certificate of Analysis (COA)

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Protocols & Articles
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PHR1834 Itraconazole, Pharmaceutical Secondary Standard; Certified Reference Material

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