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 | |
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ABCB1 |
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CYP2C19 |
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Publications |
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CYP2C9 |
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Publications |
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CYP2E1 |
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Publications |
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CYP3A4 |
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Publications |
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CYP3A5 |
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Publications |
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UGT1A1 |
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Publications |
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UGT1A7 |
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Publications |
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UGT1A9 |
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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 | |
|---|---|---|---|
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losartan |
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Publications |
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nateglinide |
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Publications |
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tacrolimus |
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zidovudine |
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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 | |
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Candidiasis |
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Publications |
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Candidiasis, Oral |
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Mycoses |
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Neutropenia |
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Transplantation |
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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.
- Drug-Induced Long QT Intervals




- 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.
Downloads
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LinkOuts
Common Searches
Search PubMed
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Non-Curated Publications
A list of non-curated publications that mention this drug is available.
