QuickView for fluconazole (compound)

Summary
General Info

PubChem

PubChem Compound 3365

Name:	Fluconazole
PubChem Compound ID:	3365
Description:	Triazole antifungal agent that is used to treat oropharyngeal candidiasis and cryptococcal meningitis in AIDS.
Molecular formula:	C₁₃H₁₂F₂N₆O
Molecular weight:	306.271 g/mol
Synonyms:	Spectrum2_001607; 2-(2,4-Difluorophenyl)-1,3-di-1H-1,2,4-triazol-1-ylpropan-2-ol; Triflucan; .alpha.-(2,4-Difluorophenyl)-.alpha.-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol; Zoltec; 2-(2,4-DIFLUOROPHENYL)-1,3-DI(1H-1,2,4-TRIAZOL-1-YL)PROPAN-2-OL; NINDS_001030; Spectrum4_000090; Flukezol; AIDS-112166. show more » Spectrum2_001607; 2-(2,4-Difluorophenyl)-1,3-di-1H-1,2,4-triazol-1-ylpropan-2-ol; Triflucan; .alpha.-(2,4-Difluorophenyl)-.alpha.-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol; Zoltec; 2-(2,4-DIFLUOROPHENYL)-1,3-DI(1H-1,2,4-TRIAZOL-1-YL)PROPAN-2-OL; NINDS_001030; Spectrum4_000090; Flukezol; AIDS-112166; Fluconazole [USAN:BAN:INN:JAN]; AIDS-121430; Fluconazol [Spanish]; Diflucan (TN); D00322; Pritenzol; 86386-73-4; Zemyc; Mutum; Flucazol; XMP.391 & Fluconazole; FCZ; FLC; GL663142 & Fluconazole; Biocanol; Forcan; Fluconazole & Human recombinant granulocyte colony stimulating factor; AIDS-010227; AIDS-110399; TPF; Afungil; Loitin; 1H-1,2,4-Triazole-1-ethanol, .alpha.-(2,4-difluorophenyl)-.alpha.-(1H-1,2,4-triazol-1-ylmethyl)-; FLU; Alflucoz; DivK1c_001030; FLZ; CCRIS 7211; Dimycon; Cryptal; AIDS-010197; AIDS-000315; Flucytosine & Nyotran(Liposomal Nystatin); AIDS093051; Flusol; Fungata; KBio2_007270; Fluconazole & hGCSF; Syscan; Fluconazole (JAN/USAN); alpha-(2,4-Difluorophenyl)-alpha-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol; Fluconazolum [Latin]; AIDS010197; Fluconazole & MC-510,011; XMP.284 & Fluconazole; Zonal; 2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)-2-propanol; Baten; Fluzone; Diflucan; KBio2_002134; 2-(2,4-Difluoro-phenyl)-1,3-bis-[1,2,4]triazol-1-yl-propan-2-ol; KBioSS_002134; AIDS110401; AIDS000315; SPBio_001613; FLCZ; AIDS110400; DRG-0005; Fluconazole; Fluconazole & Bovine Lactoferrin; CHEBI:5099; Spectrum_001654; 2-(2,4-difluorophenyl)-1,3-bis-(1H-1,2,4-triazol-1-yl)propan-2-ol; Spectrum3_001912; KBioGR_000360; Oxifugol; KBio1_001030; 2,4-Difluoro-alpha,alpha-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcohol; Flucytosine & Nyotran; UK-49858; ALPHA-(2,4-DIFLUOROPHENYL)-ALPHA-(1H-1,2,4-TRIAZOLE-1-YLMETHYL)-1H-1,2,4-TRIAZOLE-1-ETHANOL; AIDS121430; KBio3_003009; AIDS112166; Flunizol; AIDS-093051; Biozolene; UK 49858; AIDS-110400; AIDS-110401; AIDS010227; KBio2_004702; XMP.366 & Fluconazole; Canzol; 1H-1,2,4-Triazole-1-ethanol, alpha-(2,4-difluorophenyl)-alpha-(1H-1,2,4-triazol-1-ylmethyl)-; Elazor; AIDS110399; Flucostat show less «

DrugBank

Identification

Name:	Fluconazole
Name (isomeric):	DB00196
Drug Type:	small molecule
Description:	Triazole antifungal agent that is used to treat oropharyngeal candidiasis and cryptococcal meningitis in AIDS.
Brand:	Flunizol, Elazor, Diflucan, Flukezol, Biozolene, Triflucan, Flucazol, Biocanol, Pritenzol, Flucostat, Flusol
Category:	Antifungal Agents, Antifungals
CAS number:	86386-73-4

Pharmacology

Indication:	For the treatment of fungal infections.
Pharmacology:	Fluconazole, a synthetic antifungal agent of the imidazole class, is used to treat vaginal candidiasis. It inhibits the fungal lanosterol 14 alpha-demethylase which thereby prevents the formation of ergosterol which is an essential component in the fungal cell membrane.
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 respirat... show more » 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. show less «
Absorption:	90%
Protein binding:	11 to 12%
Biotransformation:	Hepatic
Route of elimination:	In normal volunteers, fluconazole is cleared primarily by renal excretion, with approximately 80% of the administered dose appearing in the urine as unchanged drug.
Half Life:	30 hours (range 20-50 hours)
Clearance:	0.23 mL/min/Kg [adults] 0.18 mL/min/Kg [In premature newborns within 36 hours of birth] 0.22 mL/min/Kg [In premature newborns 6 days old] 0.33 mL/min/Kg [In premature newborns 12 days old] 0.4 mL/min/kg [9 Months-13 yearsreceiving single-oral 2 mg/kg] 0.51 mL/min/Kg [9 Months-13 yearsreceiving single-oral 8 mg/kg] 0.49 mL/min/Kg [5-15 yearsreceiving multiple IV 2 mg/kg] 0.59 mL/min/Kg [5-15 yearsreceiving multiple IV 4 mg/kg] 0.66 mL/min/Kg [5-15 yearsreceiving multiple IV 8 mg/kg]
Toxicity:	Symptoms of overdose include hallucinations and paranoid behavior.
Affected organisms:	Fungi

Interactions

Food interaction:

Take without regard to meals.

Drug interaction:

Acenocoumarol	Fluconazole may increase the serum concentration of acenocoumarol by decreasing its metabolism.
Tolterodine	Fluconazole may decrease the metabolism and clearance of tolterodine. Adjust tolterodine dose and monitor for efficacy and toxicity.
Diazepam	Fluconazole may increase the effect of the benzodiazepine, diazepam.
Halazepam	Fluconazole may increase the effect of the benzodiazepine, halazepam.
Lumefantrine	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.

Acenocoumarol	Fluconazole may increase the serum concentration of acenocoumarol by decreasing its metabolism.
Tolterodine	Fluconazole may decrease the metabolism and clearance of tolterodine. Adjust tolterodine dose and monitor for efficacy and toxicity.
Diazepam	Fluconazole may increase the effect of the benzodiazepine, diazepam.
Halazepam	Fluconazole may increase the effect of the benzodiazepine, halazepam.
Lumefantrine	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Conivaptan	Antifungal Agents (Azole Derivatives, Systemic) may decrease the metabolism of Conivaptan. Concomitant use of conivaptan with strong CYP3A4 inhibitors (e.g., azole antifungals) is contraindicated.
Dihydroergotamine	Possible ergotism and severe ischemia with this combination
Voriconazole	Fluconazole, a strong CYP2C9 inhibitor, may increase the serum concentration of voriconazole by decreasing its metabolism. Additive QTc prolongation may also occur. Consider alternate therapy or monitor for QTc prolongation and changes in the therapeutic and adverse effects of voriconazole if fluconazole is initiated, discontinued or dose changed.
Estazolam	Fluconazole may increase the effect of the benzodiazepine, estazolam.
Everolimus	Fluconazole may increase everolimus levels/toxicity.
Clorazepate	Fluconazole may increase the effect of the benzodiazepine, clorazepate.
Simvastatin	Increased risk of myopathy/rhabdomyolysis
Trazodone	The CYP3A4 inhibitor, Fluconazole, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Fluconazole is initiated, discontinued or dose changed.
Torasemide	Fluconazole, a strong CYP2C9 inhibitor, may increase the serum concentration of Torasemide, a CYP2C9 substrate, by decreasing Torasemide metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Torasemide if Fluconazole is initiated, discontinued or dose changed.
Cilostazol	Fluconazole may decrease the effect of cilostazol.
Lovastatin	Increased risk of myopathy/rhabdomyolysis
Tamoxifen	Fluconzole may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Fluconazole is initiated, discontinued or dose changed.
Tolbutamide	Fluconazole, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Fluconazole therapeutic and adverse effects if Delavirdine is initiated, discontinued or dose changed.
Pimozide	Increased risk of cardiotoxicity and arrhythmias
Valdecoxib	Fluconazole may increase the effect and toxicity of valdecoxib.
Mephenytoin	Increases the effect of hydantoin
Tacrolimus	Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. The antifungal, fluconazole, may also increase serum concentrations of tacrolimus.
Verapamil	Fluconazole may increase the serum concentration of Verapamil by decreasing Verapamil metabolism. This likely occurs via Fluconazole-mediated CYP3A4 inhibition. Monitor for changes in the therapeutic/adverse effects of Verapamil if Fluconazole is initiated, discontinued, or dose changed.
Cyclophosphamide	Fluconazole reduces metabolism and clearance of cyclophosphamide.
Artemether	Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
Vincristine	Increases the effect and toxicity of anticancer agent
Trimipramine	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Fluconazole, a strong CYP2C19 inhibitor, may also decrease the metabolism and clearance of Trimipramine, a CYP2C19 substrate. Concomitant therapy should be used with caution.
Tramadol	Fluconazole may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
Toremifene	Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
Bromazepam	Fluconazole may increase the serum concentration of bromazepam by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of bromazepam if fluconazole is initiated, discontinued or dose changed.
Trimethoprim	The strong CYP2C9 inhibitor, Fluconazole, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Fluconazole is initiated, discontinued or dose changed.
Dicumarol	Fluconazole may increase the serum concentration of dicumarol by decreasing its metabolism.
Carbamazepine	Fluconazole may increase the therapeutic and adverse effects of carbamazepine.
Cyclosporine	Fluconazole may increase the therapeutic and adverse effects of the cyclosporine.
Vinblastine	Increases the effect and toxicity of anticancer agent
Midazolam	Fluconazole may increase the effect of the benzodiazepine, midazolam.
Zafirlukast	Fluconazole, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of zafirlukast. Consider alternate therapy or monitor for changes in zafirlukast therapeutic and adverse effects if fluconazole is initiated, discontinued or dose changed.
Phenytoin	Fluconazole may increase the therapeutic and adverse effects of phenytoin.
Imipramine	Fluconazole may increase the effect and toxicity of the tricyclic antidepressant, imipramine, by decreasing its metabolism. Additive QTc-prolonging effects may also occur. Monitor for changes in the therapeutic and adverse effects of imipramine if fluconazole is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
Fentanyl	Fluconazole may increase levels/toxicity of fentanyl.
Rifabutin	Fluconazole may increase levels/toxicity of rifabutin.
Ramelteon	Fluconazole may increase the serum levels and toxcity of ramelteon.
Tamsulosin	Fluconzole, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Fluconazole is initiated, discontinued, or dose changed.
Ranolazine	Increased levels of ranolazine - risk of toxicity
Zuclopenthixol	Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Fosphenytoin	Fluconazole may increase the effect of hydantoin.
Alfentanil	Increases the effect and toxicity of alfentanil
Carisoprodol	Strong CYP2C19 inhibitors such as fluconazole may decrease the metabolism of CYP2C19 substrates such as carisoprodol. Consider an alternative for one of the interacting drugs in order to avoid toxicity of the substrate. Some combinations are specifically contraindicated by manufacturers. Suggested dosage adjustments are also offered by some manufacturers. Please review applicable package inserts. Monitor for increased effects of the CYP substrate if a CYP inhibitor is initiated/dose increased, and decreased effects if a CYP inhibitor is discontinued/dose decreased.
Haloperidol	Fluconazole may increase the effect and toxicity of haloperidol.
Clonazepam	Fluconazole may increase the effect of the benzodiazepine, clonazepam.
Amitriptyline	Fluconazole may increase the effect and toxicity of the tricyclic antidepressant, amitriptyline, by decreasing its metabolism. Additive QTc-prolonging effects may also occur. Monitor for changes in the therapeutic and adverse effects of amitriptyline if fluconazole is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
Thiothixene	May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
Nortriptyline	Fluconazole may increase the effect and toxicity of the tricyclic antidepressant, nortriptyline, by decreasing its metabolism. Additive QTc-prolonging effects may also occur. Monitor for changes in the therapeutic and adverse effects of nortriptyline if fluconazole is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
Vorinostat	Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Rifampin	Rifampin may decrease the effect of fluconazole.
Celecoxib	Fluconazole may increase the effect of celecoxib.
Triazolam	Fluconazole may increase the effect of the benzodiazepine, triazolam.
Terfenadine	Increased risk of cardiotoxicity and arrhythmias
Anisindione	Fluconazole may increase the serum concentration of anisindione by decreasing its metabolism.
Fluvastatin	Fluconazole may increase the serum concentration of fluvastatin by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of fluvastatin if fluconazole is initiated, discontinued or dose changed.
Atorvastatin	Increased risk of myopathy/rhabdomyolysis
Ziprasidone	Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
Eplerenone	This CYP3A4 inhibitor increases the effect and toxicity of eplerenone
Alprazolam	Fluconazole may increase the effect of the benzodiazepine, alprazolam.
Zolpidem	Fluconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of zolpidem by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zolpidem if fluconazole is initiated, discontinued or dose changed.
Tipranavir	Fluconazole may increase the serum concentration of Tipranavir. Dose adjustments are not required.
Ergotamine	Possible ergotism and severe ischemia with this combination
Warfarin	Fluconazole, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if fluconazole is initiated, discontinued or dose changed.
Cisapride	Increased risk of cardiotoxicity and arrhythmias
Chlordiazepoxide	Fluconazole may increase the effect of the benzodiazepine, chlordiazepoxide.
Flurazepam	Fluconazole may increase the effect of the benzodiazepine, flurazepam.
Ethotoin	Increases the effect of hydantoin
Quazepam	Fluconazole may increase the effect of the benzodiazepine, quazepam.

Targets

Enzymes

Cytochrome P450 11B1, mitochondrial

Transporters

Multidrug resistance protein 1