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1354251

USP

Itraconazole

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

Oriconazole, R51211, Sporanox

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Size/SKUAvailabilityPrice
100 mg

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$455.00

About This Item

Empirical Formula (Hill Notation):
C35H38Cl2N8O4
CAS Number:
84625-61-6
Molecular Weight:
705.63
NACRES:
NA.24
PubChem Substance ID:
329750213
UNSPSC Code:
41116107
MDL number:
MFCD00870168
eCl@ss:
25140904

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grade

pharmaceutical primary standard

agency

USP

API family

itraconazole

manufacturer/tradename

USP

application(s)

pharmaceutical
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

General description

Find answers to frequently asked questions on USP products in USP FAQs.
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.
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.

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.

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Itraconazole United States Pharmacopeia (USP) Reference Standard

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Itraconazole for system suitability European Pharmacopoeia (EP) Reference Standard

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Itraconazole for system suitability

Hh Signaling Antagonist X, Itraconazole The Hh Signaling Antagonist X, Itraconazole, also referenced under CAS 84625-61-6, controls the biological activity of Hh pathway. This small molecule/inhibitor is primarily used for Cell Signaling applications.

Sigma-Aldrich

419825

Hh Signaling Antagonist X, Itraconazole

description

United States Pharmacopeia (USP) Reference Standard

description

Pharmaceutical Secondary Standard; Certified Reference Material

description

European Pharmacopoeia (EP) Reference Standard

description

The Hh Signaling Antagonist X, Itraconazole, also referenced under CAS 84625-61-6, controls the biological activity of Hh pathway. This small molecule/inhibitor is primarily used for Cell Signaling applications.

grade

pharmaceutical primary standard

grade

certified reference material, pharmaceutical secondary standard

grade

pharmaceutical primary standard

grade

-

manufacturer/tradename

USP

manufacturer/tradename

-

manufacturer/tradename

EDQM

manufacturer/tradename

Calbiochem®

application(s)

pharmaceutical
pharmaceutical (small molecule)

application(s)

pharmaceutical
pharmaceutical (small molecule)
pharmaceutical

application(s)

pharmaceutical
pharmaceutical (small molecule)

application(s)

-

format

neat

format

neat

format

neat

format

-

agency

USP

agency

traceable to Ph. Eur. I7000000, traceable to USP 1354251

agency

-

agency

-

API family

itraconazole

API family

itraconazole

API family

itraconazole

API family

-

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Codes

H302

Storage Class

11 - Combustible Solids

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

WGK

WGK 1

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