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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB01167
rdf:type
n7:Drug
n7:description
One of the triazole antifungal agents that inhibits cytochrome P-450-dependent enzymes resulting in impairment of ergosterol synthesis. It has been used against histoplasmosis, blastomycosis, cryptococcal meningitis & aspergillosis. [PubChem]
n7:dosage
n30:271B4D65-363D-11E5-9242-09173F13E4C5 n30:271B4D66-363D-11E5-9242-09173F13E4C5 n30:271B4D64-363D-11E5-9242-09173F13E4C5
n7:group
approved investigational
n7:halfLife
21 hours
n7:indication
For the treatment of the following fungal infections in immunocompromised and non-immunocompromised patients: pulmonary and extrapulmonary blastomycosis, histoplasmosis, aspergillosis, and onychomycosis.
owl:sameAs
n6:DB01167 n22:DB01167
dcterms:title
Itraconazole
adms:identifier
n10:PA450132 n12:55283 n13:D00350 n14:50458-295-15 n15:DB01167 n17:6076 n18:49927 n24:Itraconazole n31:46505954
n7:mechanismOfAction
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 respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.
n7:packager
n23:271B4D54-363D-11E5-9242-09173F13E4C5 n23:271B4D55-363D-11E5-9242-09173F13E4C5 n23:271B4D53-363D-11E5-9242-09173F13E4C5 n23:271B4D58-363D-11E5-9242-09173F13E4C5 n23:271B4D59-363D-11E5-9242-09173F13E4C5 n23:271B4D56-363D-11E5-9242-09173F13E4C5 n23:271B4D57-363D-11E5-9242-09173F13E4C5 n23:271B4D5C-363D-11E5-9242-09173F13E4C5 n23:271B4D5D-363D-11E5-9242-09173F13E4C5 n23:271B4D5A-363D-11E5-9242-09173F13E4C5 n23:271B4D5B-363D-11E5-9242-09173F13E4C5 n23:271B4D5E-363D-11E5-9242-09173F13E4C5
n7:patent
n11:6407079 n11:1336498 n11:5633015 n11:2142848
n7:routeOfElimination
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.
n7:synonym
Itrizole (tn) Sporanox (tn) Oriconazole Itraconazole Itraconazolum Itraconazol
n7: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.
n7:volumeOfDistribution
* 796 ± 185 L
n25:hasAHFSCode
n26:08-14-08
n7:foodInteraction
Take with food. Avoid taking with grapefruit juice. Take after a full meal. Avoid milk, calcium containing dairy products, iron, antacids, or aluminum salts 2 hours before or 6 hours after using antacids while on this medication.
n7:proteinBinding
99.8%
n7:synthesisReference
Jong-Soo Woo, Hong-Gi Yi, "Antifungal oral composition containing itraconazole and process for preparing same." U.S. Patent US6039981, issued May, 1998.
n28:hasConcept
n29:M0027131
foaf:page
n4:itraconazole.html n16:spo1411.shtml n20:itraconazole.htm
n7:IUPAC-Name
n8:271B4D6B-363D-11E5-9242-09173F13E4C5
n7:InChI
n8:271B4D71-363D-11E5-9242-09173F13E4C5
n7:Molecular-Formula
n8:271B4D70-363D-11E5-9242-09173F13E4C5
n7:Molecular-Weight
n8:271B4D6D-363D-11E5-9242-09173F13E4C5
n7:Monoisotopic-Weight
n8:271B4D6E-363D-11E5-9242-09173F13E4C5
n7:SMILES
n8:271B4D6F-363D-11E5-9242-09173F13E4C5
n7:Water-Solubility
n8:271B4D80-363D-11E5-9242-09173F13E4C5 n8:271B4D69-363D-11E5-9242-09173F13E4C5
n7:logP
n8:271B4D82-363D-11E5-9242-09173F13E4C5 n8:271B4D67-363D-11E5-9242-09173F13E4C5 n8:271B4D6A-363D-11E5-9242-09173F13E4C5
n7:logS
n8:271B4D68-363D-11E5-9242-09173F13E4C5
n7:pKa
n8:271B4D83-363D-11E5-9242-09173F13E4C5
n25:hasATCCode
n27:J02AC02
n7:H-Bond-Acceptor-Count
n8:271B4D77-363D-11E5-9242-09173F13E4C5
n7:H-Bond-Donor-Count
n8:271B4D78-363D-11E5-9242-09173F13E4C5
n7:InChIKey
n8:271B4D72-363D-11E5-9242-09173F13E4C5
n7:Polar-Surface-Area--PSA-
n8:271B4D73-363D-11E5-9242-09173F13E4C5
n7:Polarizability
n8:271B4D75-363D-11E5-9242-09173F13E4C5
n7:Refractivity
n8:271B4D74-363D-11E5-9242-09173F13E4C5
n7:Rotatable-Bond-Count
n8:271B4D76-363D-11E5-9242-09173F13E4C5
n7:absorption
The absolute oral bioavailability of itraconazole is 55%, and is maximal when taken with a full meal.
n7:affectedOrganism
Fungi, yeast and protozoans
n7:casRegistryNumber
84625-61-6
n7:category
n7:clearance
* 381 +/- 95 mL/minute [IV administration]
n7:containedIn
n19:271B4D5F-363D-11E5-9242-09173F13E4C5 n19:271B4D62-363D-11E5-9242-09173F13E4C5 n19:271B4D63-363D-11E5-9242-09173F13E4C5 n19:271B4D60-363D-11E5-9242-09173F13E4C5 n19:271B4D61-363D-11E5-9242-09173F13E4C5
n7:Bioavailability
n8:271B4D7C-363D-11E5-9242-09173F13E4C5
n7:Ghose-Filter
n8:271B4D7E-363D-11E5-9242-09173F13E4C5
n7:MDDR-Like-Rule
n8:271B4D7F-363D-11E5-9242-09173F13E4C5
n7:Melting-Point
n8:271B4D81-363D-11E5-9242-09173F13E4C5
n7:Number-of-Rings
n8:271B4D7B-363D-11E5-9242-09173F13E4C5
n7:Physiological-Charge
n8:271B4D7A-363D-11E5-9242-09173F13E4C5
n7:Rule-of-Five
n8:271B4D7D-363D-11E5-9242-09173F13E4C5
n7:Traditional-IUPAC-Name
n8:271B4D6C-363D-11E5-9242-09173F13E4C5
n7:pKa--strongest-basic-
n8:271B4D79-363D-11E5-9242-09173F13E4C5