Rx00136 - Ketoconazole


Name:
Ketoconazole
Rx ID:
Rx00136
Validation Level:
Phenomic Similarity:
0.588
Reference ID:
DB01026
Primary Indications:
Nephrotoxicity; organ transplantation
Orphan Indications:
No annotated orphan indications.
Rare Indications:
No annotated rare indications.
Common Indications:
Systemic fungal infections; candidiasis; chronic mucocutaneous candidiasis; oral thrush; candiduria; blastomycosis; coccidioidomycosis; histoplasmosis; chromomycosis; paracoccidioidomycosis; severe recalcitrant cutaneous dermatophyte infections
Drug Interactions:
Abiraterone; Acenocoumarol; Alfentanil; Alfuzosin; Aliskiren; Almotriptan; Alprazolam; Aluminium; Amitriptyline; Anisindione; ...
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Food Interactions:
Avoid alcohol. 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 with food.

Interactive 3D Model

Interactive Drug Target Network

Interactive Bipartite Drug Repurposing Graph

Rx00136
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
nephrotoxicity systemic fungal infections 209 1300 52130 12.444 1.28E-141 4.1e-138

Chemical, Pharmacological and Biological Annotations


ATC Code:
D01AC08; G01AF11 J02AB02;
Brands:
Fungarest (Janssen-Cilag); Fungoral (Johnson & Johnson); Ketoderm (Hessel); Ketoisdin (Isdin); Ketozole (Ranbaxy); Nizoral Cream (Ortho-McNeil); Nizoral Shampoo (Ortho-McNeil); Orifungal (Janssen); Orifungal M (Janssen); Panfungol (Esteve)
Categories:
Antifungal Agents; 14-alpha Demethylase Inhibitors
ChEBI ID:
48339
KEGG Drug ID:
D00351
SMILE:
CC(=O)N1CCN(CC1)C1=CC=C(OCC2COC(CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1
InChI:
1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3
Classification:
Kingdom:
Organic Compounds
Superclass:
Heterocyclic Compounds
Class:
Piperazines
Subclass:
Phenylpiperazines
Indication:
For the treatment of the following systemic fungal infections: candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis.
Pharmacodynamics:
Ketoconazole, like clotrimazole, fluconazole, itraconazole, and miconazole, is an imidazole antifungal agent.
Description:
Broad spectrum antifungal agent used for long periods at high doses, especially in immunosuppressed patients. [PubChem]
Mechanism:
Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability. Other mec...
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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:
Inhibitor
Renal organic cation transporter:
Non-inhibitor
CYP450 2C9 substrate:
Inhibitor
CYP450 2D6 substrate:
Inhibitor
CYP450 2C19 substrate:
Inhibitor
CYP450 inhibitory promiscuity:
High CYP Inhibitory Promiscuity
Ames test:
Non AMES toxic
Carcinogenicity:
Non-carcinogens
Biodegradation:
Not ready biodegradable
Rat acute toxicity:
3.4739 LD50, mol/kg
hERG inhibition (predictor I):
Weak inhibitor
hERG inhibition (predictor II):
Inhibitor

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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