PharmGKB: The Pharmacogenomics Knowledge Base

Drug/Small Molecule:
fluconazole

2D structure

Overview

Trade Names: Biocanol; Biozolene; Diflucan; Elazor; Flucazol; Flucostat; Flukezol; Flunizol; Flusol; Pritenzol; Triflucan
PharmGKB Accession Id: PA449653

Description

Triazole antifungal agent that is used to treat oropharyngeal candidiasis and cryptococcal meningitis in AIDS. PubChem (source: Drug Bank)

Indication

For the treatment of fungal infections. (source: Drug Bank)

ATC Therapeutic Categories

  • D01AC:Imidazole and triazole derivatives
  • J02AC:Triazole derivatives

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

Fluconazole 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. Fluconazole 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. (source: Drug Bank)

Pharmacology

Fluconazole, a synthetic antifungal agent of the imidazole class, is used to treat vaginal candidiasis. (source: Drug Bank)

Food Interactions

Take without regard to meals. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic (source: Drug Bank)

Protein Binding

11 to 12% (source: Drug Bank)

Absorption

90% (source: Drug Bank)

Toxicity

Symptoms of overdose include hallucinations and paranoid behavior. (source: Drug Bank)

Isomeric SMILES Code:

c1cc(c(cc1F)F)C(Cn2cncn2)(Cn3cncn3)O (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Has annotations
ABCB1
  •   
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  • PK
  • FA
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP2C19
  •   
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Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP2C9
  •   
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  • PK
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Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
CYP2E1
  •   
  •   
  • PK
  •   
  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A4
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Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A5
  •   
  •   
  • PK
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
UGT1A1
  •   
  •   
  • PK
  • FA
  •   
Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
UGT1A7
  •   
  •   
  • PK
  • FA
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Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
UGT1A9
  •   
  •   
  • PK
  • FA
  •   
Publications

A list of non-curated publications that mention this drug along with other genes is available.

Drug Targets

Gene Description
CYP51A1 Uncurated Annotation (source: Drug Bank)

The following drugs are in curated knowledge about this drug.

  Drug Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
losartan
  •   
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  • PK
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
nateglinide
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  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
tacrolimus
  •   
  •   
  • PK
  •   
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
zidovudine
  •   
  •   
  • PK
  • FA
  •   
Publications

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

Drug Description
acenocoumarol Uncurated Annotation Increases the anticoagulant effect (source: Drug Bank)
alfentanil Uncurated Annotation Increases the effect and toxicity of alfentanil (source: Drug Bank)
alprazolam Uncurated Annotation Increases the effect of the benzodiazepine (source: Drug Bank)
amitriptyline Uncurated Annotation The imidazole increases the effect and toxicity of the tricyclic (source: Drug Bank)
atorvastatin Uncurated Annotation Increased risk of myopathy/rhabdomyolysis (source: Drug Bank)
carbamazepine Uncurated Annotation Increases the effect of carbamazepine (source: Drug Bank)
celecoxib Uncurated Annotation Increases the effect of celecoxib (source: Drug Bank)
chlordiazepoxide Uncurated Annotation Increases the effect of the benzodiazepine (source: Drug Bank)
cisapride Uncurated Annotation Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
clonazepam Uncurated Annotation Increases the effect of the benzodiazepine (source: Drug Bank)
cyclophosphamide Uncurated Annotation Reduces metabolism and clearance of cyclophosphamide (source: Drug Bank)
cyclosporine Uncurated Annotation Increases the effect of the immunosuppressant (source: Drug Bank)
diazepam Uncurated Annotation Increases the effect of the benzodiazepine (source: Drug Bank)
dicumarol Uncurated Annotation Increases the anticoagulant effect (source: Drug Bank)
estazolam Uncurated Annotation Increases the effect of the benzodiazepine (source: Drug Bank)
fentanyl Uncurated Annotation The imidazole increases levels/toxicity of fentanyl (source: Drug Bank)
flurazepam Uncurated Annotation Increases the effect of the benzodiazepine (source: Drug Bank)
fluvastatin Uncurated Annotation Increases the effect and toxicity of fluvastatin (source: Drug Bank)
haloperidol Uncurated Annotation The imidazole increases the effect and toxicity of haloperidol (source: Drug Bank)
imipramine Uncurated Annotation The imidazole increases the effect and toxicity of the tricyclic (source: Drug Bank)
lovastatin Uncurated Annotation Increased risk of myopathy/rhabdomyolysis (source: Drug Bank)
mephenytoin Uncurated Annotation Increases the effect of hydantoin (source: Drug Bank)
midazolam Uncurated Annotation Increases the effect of the benzodiazepine (source: Drug Bank)
nortriptyline Uncurated Annotation The imidazole increases the effect and toxicity of the tricyclic (source: Drug Bank)
phenytoin Uncurated Annotation Increases the effect of hydantoin (source: Drug Bank)
pimozide Uncurated Annotation Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
rifabutin Uncurated Annotation Increases levels/toxicity of rifabutin (source: Drug Bank)
rifampin Uncurated Annotation Decreases the effect of imidazole (source: Drug Bank)
simvastatin Uncurated Annotation Increased risk of myopathy/rhabdomyolysis (source: Drug Bank)
tacrolimus Uncurated Annotation Increases the effect of the immunosuppressant (source: Drug Bank)
terfenadine Uncurated Annotation Increased risk of cardiotoxicity and arrhythmias (source: Drug Bank)
triazolam Uncurated Annotation Increases the effect of the benzodiazepine (source: Drug Bank)
valdecoxib Uncurated Annotation The imidazole increases the effect and toxicity of valdecoxib (source: Drug Bank)
vinblastine Uncurated Annotation Increases the effect and toxicity of anticancer agent (source: Drug Bank)
vincristine Uncurated Annotation Increases the effect and toxicity of anticancer agent (source: Drug Bank)
warfarin Uncurated Annotation Increases the anticoagulant effect (source: Drug Bank)

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
Candidiasis
  • CO
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  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Candidiasis, Oral
  • CO
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  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Mycoses
  • CO
  •   
  •   
  •   
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Neutropenia
  • CO
  •   
  •   
  •   
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Transplantation
  • CO
  •   
  •   
  •   
  •   
Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Curated Phenotype Datasets

These datasets are sorted alphabetically by title.

  1. Drug-Induced Long QT Intervals
    • Genotype data available
    • Phenotype data available
    • No literature annotations
    • Not annotated
    • PD
    Submitted by Dan Roden, MD involving ADRB1, ADRB2, KCNE1, KCNE2, KCNH2, KCNQ1, SCN5A, almokalant, amiodarone, amitriptyline, bretylium, bupivacaine, cisapride, disopyramide, dofetilide, encainide, fluconazole, haloperidol, hydroquinidine, isoflurane, itraconazole, ketoconazole, lithium, loratadine, metoclopramide, nortriptyline, procainamide, quinidine, sematilide, sotalol, sulfamethoxazole, thioridazine, trimethoprim, , Long QT Syndrome, Proarrhythmia and Torsades de Pointes

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. Physicochemical determinants of human renal clearance
  2. The Influence of CYP3A5 Expression on the Extent of Hepatic CYP3A Inhibition Is Substrate-Dependent: An in Vitro-in Vivo Evaluation

Downloads

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LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB00196
KEGG Drug ID:
D00322
PubChem Compound ID:
3365
PubChem Substance ID:
192927

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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