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QuickView for Itraconazole (compound)

Name: Itraconazole
PubChem Compound ID: 3793
Description: A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.
Molecular formula: C35H38Cl2N8O4
Molecular weight: 705.633 g/mol
LS-1843; MLS000028582; SMR000058959; Itraconazole
Name: Itraconazole
Name (isomeric): DB01167
Drug Type: small molecule
Description: A triazole antifungal agent that inhibits cytochrome P-450-dependent enzymes required for ERGOSTEROL synthesis.
ITCZ; Itraconazolum [Latin]; Itraconazol [Spanish]; ITR; ITC; ITZ
Brand: Sporal, Oriconazole, Triasporn, Hyphanox, Itrizole, Sporanox, Sporonox, Sporanos
Category: Antiprotozoal Agents, Antifungal Agents, Antiprotozoals, Antifungals
CAS number: 84625-61-6
Indication: For the treatment of the following fungal infections in immunocompromised and non-immunocompromised patients: pulmonary and extrapulmonary blastomycosis, histoplasmosis, aspergillosis, and onychomycosis.
Itraconazole is an imidazole/triazole type antifungal agent. Itraconazole is a highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethylation via the inhibition of the enzyme cytochrome P450 14α-demethylase. This enzyme converts lanosterol to ergosterol, and is required in fungal cell wall synthesis. The subsequent lo...
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Mechanism of Action:
Itraconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Itraconazole may also inhibit endogenous respir...
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Absorption: The absolute oral bioavailability of itraconazole is 55%, and is maximal when taken with a full meal.
Protein binding: 99.8%
Biotransformation: Itraconazole is extensively metabolized by the liver into a large number of metabolites, including hydroxyitraconazole, the major metabolite. The main metabolic pathways are oxidative scission of the dioxolane ring, aliphatic oxidation at the 1-methylpropyl substituent, N-dealkylation of this 1-methylpropyl substituent, oxidative degradation of the piperazine ring and triazolone scission.
Route of elimination: Itraconazole is metabolized predominately by the cytochrome P450 3A4 isoenzyme system (CYP3A4) in the liver, resulting in the formation of several metabolites, including hydroxyitraconazole, the major metabolite. Fecal excretion of the parent drug varies between 3-18% of the dose. Renal excretion of the parent drug is less than 0.03% of the dose. About 40% of the dose is excreted as inactive metabolites in the urine. No single excreted metabolite represents more than 5% of a dose.
Half Life: 21 hours
Clearance: 381 +/- 95 mL/minute [IV administration]
Toxicity: No significant lethality was observed when itraconazole was administered orally to mice and rats at dosage levels of 320 mg/kg or to dogs at 200 mg/kg.
Affected organisms: Fungi, yeast and protozoans
Food interaction:
Avoid taking with grapefruit juice.
Avoid milk, calcium containing dairy products, iron, antacids, or aluminum salts 2 hours before or 6 hours after using antacids while on this medication.
Take after a full meal.
Take with food.
Drug interaction:
OmeprazoleThe proton pump inhibitor, omeprazole, may decrease the absorption of itraconazole.
ClorazepateItraconazole may increase the effect of the benzodiazepine, clorazepate.
TiagabineThe strong CYP3A4 inhibitor, Itraconazole, may decrease the metabolism and clearance of Tiagabine, a CYP3A4 substrate. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Tiagabine if Itraconazole is initiated, discontinued or dose changed.
PrednisoloneThe imidazole, itraconazole, may increase the effect and toxicity of the corticosteroid, prednisolone.
ConivaptanAntifungal Agents (Azole Derivatives, Systemic) may decrease the metabolism of Conivaptan. Concomitant use of conivaptan with strong CYP3A4 inhibitors (e.g., azole antifungals) is contraindicated.
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