Rx00135 - Itraconazole


Name:
Itraconazole
Rx ID:
Rx00135
Validation Level:
Phenomic Similarity:
0.498
Reference ID:
DB01167
Primary Indications:
Fungal otitis externa; otomycosis
Orphan Indications:
No annotated orphan indications.
Rare Indications:
No annotated rare indications.
Common Indications:
Fungal infection; febrile neutropenia; immunodeficiency; pulmonary blastomycosis; blastomycosis extrapulmonary; histoplasmosis; chronic cavitary pulmonary disease; disseminated, non-meningeal histoplasmosis; pulmonary aspergillosis; extrapulmonary aspergillosis
Drug Interactions:
Abiraterone; Acenocoumarol; Alfentanil; Alfuzosin; Aliskiren; Almotriptan; Alprazolam; Aluminium; Anisindione; Apixaban; ...
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Food Interactions:
Avoid milk, calcium containing dairy products, iron, antacids, or aluminum salts 2 hours before or 6 hours after using antacids while on this medication. Avoid taking with grapefruit juice. Take after a full meal. Take with food.

Interactive 3D Model

Interactive Drug Target Network

Interactive Bipartite Drug Repurposing Graph

Rx00135
Primary Indication
Secondary Indication

Visualize Chemical Properties

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Disease prevalence from Electronic Health Records

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Disease A Disease B A∩B A∩¬B B∩¬A Odds-Ratio P-Value Adjusted P-Value
otomycosis fungal infection 1402 1402 52130 77.401 0 0.0
fungal otitis externa fungal infection 1814 11423 52130 12.291 0 0.0

Chemical, Pharmacological and Biological Annotations


ATC Code:
J02AC02
Brands:
Itrizole; Oriconazole; Sporal
Categories:
Antifungal Agents; Antiprotozoal Agents; 14-alpha Demethylase Inhibitors
ChEBI ID:
6076
PubChem ID:
55283
KEGG Drug ID:
D00350
SMILE:
CCC(C)N1N=CN(C1=O)C1=CC=C(C=C1)N1CCN(CC1)C1=CC=C(OC[C@H]2CO[C@@](CN3C=NC=N3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1
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/t25?,31-,35-/m0/s1
Classification:
Kingdom:
Organic Compounds
Superclass:
Heterocyclic Compounds
Class:
Piperazines
Subclass:
Phenylpiperazines
Indication:
For the treatment of the following fungal infections in immunocompromised and non-immunocompromised patients: pulmonary and extrapulmonary blastomycosis, histoplasmosis, aspergillosis, and onychomycosis.
Pharmacodynamics:
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. T...
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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. [PubCh...
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Mechanism:
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 increas...
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Adsorption, Distribution, Metabolism, Excretion and Toxicity


Human Intestinal Absorption:
+
Blood Brain Barrier:
-
Caco-2 permeable:
+
P-glycoprotein substrate:
Substrate
P-glycoprotein inhibitor I:
Inhibitor
P-glycoprotein inhibitor II:
Non-inhibitor
Renal organic cation transporter:
Non-inhibitor
CYP450 2C9 substrate:
Inhibitor
CYP450 2D6 substrate:
Non-inhibitor
CYP450 2C19 substrate:
Inhibitor
CYP450 inhibitory promiscuity:
High CYP Inhibitory Promiscuity
Ames test:
AMES toxic
Carcinogenicity:
Non-carcinogens
Biodegradation:
Not ready biodegradable
Rat acute toxicity:
3.3118 LD50, mol/kg
hERG inhibition (predictor I):
Weak inhibitor
hERG inhibition (predictor II):
Inhibitor

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Please contact us if you have questions or comments about RepurposeDB. You can also contact us if you need help in submitting your drug repositioning investigation to RepurposeDB.


Dudley Laboratory
Department of Genetics and Genomic Sciences
Icahn Institute for Genomics and Multiscale Biology
Icahn School of Medicine at Mount Sinai
One Gustave L. Levy Place, Box 1498
Manhattan, New York City, NY
repurposedb@dudleylab.org