PharmGKB: The Pharmacogenomics Knowledge Base

Drug/Small Molecule:
fluconazole

2D structure

Overview

IUPAC Name: 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol
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]

Indication

For the treatment of fungal infections.

ATC Therapeutic Categories

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

Pharmacology and Interactions

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.

Pharmacology

Fluconazole, a synthetic antifungal agent of the imidazole class, is used to treat vaginal candidiasis.

Food Interactions

Take without regard to meals.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic

Protein Binding

11 to 12%

Absorption

90%

Half Life

30 hours (range 20-50 hours)

Toxicity

Symptoms of overdose include hallucinations and paranoid behavior.

Chemical Properties

Chemical Formula:

C13H12F2N6O

SMILES Code:

c1cc(c(cc1F)F)C(Cn2cncn2)(Cn3cncn3)O

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

306.2708 / 306.1041

Curated Information

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
  •   
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  • PK
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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
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  • PK
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  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
UGT1A1
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  • PK
  • FA
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Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
UGT1A7
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  • PK
  • FA
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Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
UGT1A9
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  • PK
  • FA
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Publications

Non-Curated Information

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

Metabolizing Enzymes

Drug Targets

Curated Information

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
  •   
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  • PK
  •   
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
zidovudine
  •   
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  • PK
  • FA
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Publications

Non-Curated Information

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

Drug Interactions

acenocoumarol Increases the anticoagulant effect
alfentanil Increases the effect and toxicity of alfentanil
alprazolam Increases the effect of the benzodiazepine
amitriptyline The imidazole increases the effect and toxicity of the tricyclic
anisindione Increases the anticoagulant effect
atorvastatin Increased risk of myopathy/rhabdomyolysis
carbamazepine Increases the effect of carbamazepine
celecoxib Increases the effect of celecoxib
chlordiazepoxide Increases the effect of the benzodiazepine
cilostazol Decreases the effect of cilostazol
cisapride Increased risk of cardiotoxicity and arrhythmias
clonazepam Increases the effect of the benzodiazepine
clorazepate Increases the effect of the benzodiazepine
cyclophosphamide Reduces metabolism and clearance of cyclophosphamide
cyclosporine Increases the effect of the immunosuppressant
diazepam Increases the effect of the benzodiazepine
dicumarol Increases the anticoagulant effect
dihydroergotamine Possible ergotism and severe ischemia with this combination
eplerenone This CYP3A4 inhibitor increases the effect and toxicity of eplerenone
ergotamine Possible ergotism and severe ischemia with this combination
estazolam Increases the effect of the benzodiazepine
ethotoin Increases the effect of hydantoin
everolimus The imidazole increases everolimus levels/toxicity
fentanyl The imidazole increases levels/toxicity of fentanyl
flurazepam Increases the effect of the benzodiazepine
fluvastatin Increases the effect and toxicity of fluvastatin
fosphenytoin Increases the effect of hydantoin
halazepam Increases the effect of the benzodiazepine
haloperidol The imidazole increases the effect and toxicity of haloperidol
imipramine The imidazole increases the effect and toxicity of the tricyclic
lovastatin Increased risk of myopathy/rhabdomyolysis
mephenytoin Increases the effect of hydantoin
midazolam Increases the effect of the benzodiazepine
nortriptyline The imidazole increases the effect and toxicity of the tricyclic
phenytoin Increases the effect of hydantoin
pimozide Increased risk of cardiotoxicity and arrhythmias
quazepam Increases the effect of the benzodiazepine
ramelteon This imidazole increases the levels/toxicity of ramelteon
ranolazine Increased levels of ranolazine - risk of toxicity
rifabutin Increases levels/toxicity of rifabutin
rifampin Decreases the effect of imidazole
simvastatin Increased risk of myopathy/rhabdomyolysis
tacrolimus Increases the effect of the immunosuppressant
terfenadine Increased risk of cardiotoxicity and arrhythmias
tolterodine Increases the effect and toxicity of tolterodine
triazolam Increases the effect of the benzodiazepine
valdecoxib The imidazole increases the effect and toxicity of valdecoxib
vinblastine Increases the effect and toxicity of anticancer agent
vincristine Increases the effect and toxicity of anticancer agent
warfarin Increases the anticoagulant effect

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
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
Neutropenia
  • CO
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Publications
No phenotype data No genotype data Literature annotations available Not annotated
Transplantation
  • CO
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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.

PharmGKB integrates drug information from different sources: DrugBank, Open Eye Scientific Software.
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