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Fluconazole

CHEMBL106 Phase 4 Одобрено Small molecule
Half-Life
30 hours
Bioavailability
—
Protein Binding
—
Molecular Weight
306.3 g/mol
LogP
0.4
Phase
4

By inhibiting the fungal enzyme CYP51, also called lanosterol 14-alpha-demethylase, fluconazole halts the synthesis of ergosterol, a sterol the fungal cell membrane depends on. The depleted membrane becomes leaky and the organism dies, giving this triazole antifungal its activity against yeasts and related pathogens. It is used for infections ranging from oral and vaginal thrush to systemic candidiasis and cryptococcal meningitis. A fluorinated small molecule (C13H12F2N6O) with a long half-life near 30 hours, it supports once-daily dosing and good tissue penetration. Because human sterol enzymes are far less sensitive to its action than the fungal target, fluconazole achieves selective toxicity, a property central to modern antifungal therapy. It is an approved agent widely used in both hospital and outpatient care.

This antifungal medication works by blocking the production of ergosterol, an essential component of the fungal cell membrane, causing the organism to die. It is widely used to treat fungal infections including thrush, cryptococcal meningitis, and systemic candida infections.

Молекулярная масса

306,2710 g/mol

LogP

0,40

TPSA

81,70 Ų

Правило пяти Липинского

Соответствует

Терапевтические области

Ovarian Cancer Pancreatic Cancer Bladder Cancer Thyroid Cancer Endometriosis Cardiovascular Disease Non-Small Cell Lung Cancer Oncology Inflammatory Bowel Disease Hyperlipidemia Obesity Lymphoma Breast Cancer HIV/AIDS Heart Failure Prostate Cancer Colorectal Cancer Leukemia

Классы препаратов

J — J - Antiinfectives for Systemic Use

Механизм действия

Inhibits fungal CYP51 (lanosterol 14-alpha-demethylase).

Pharmacokinetics (PK)

Half-Life 30 hours

Pharmacodynamics (PD)

Механизм

Inhibits fungal CYP51 (lanosterol 14-alpha-demethylase).

2D Структура

SVG PNG

Cite this structure


                        

                            
                            
                        

                    

                


                
                

                    

                    

                        
Embed this structure

                        

                        

                            
                            
                        

                    

                

                

                
                

                    
SMILES

                    
OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F

                

                

                
                

                    
InChI

                    
InChI=1S/C13H12F2N6O/c14-10-1-2-11(12(15)3-10)13(22,4-20-8-16-6-18-20)5-21-9-17-7-19-21/h1-3,6-9,22H,4-5H2

                

                

                

                    
                    

                        
Molecular Formula

                        
C13H12F2N6O

                    

                    
                    

                        
HBD / HBA

                        
1 / 7

                    

                    
                    

                        
Вращаемые Связи

                        
5

                    

                    
                    
                    

                        
Тяжёлые Атомы

                        
22

                    

                    
                

            


            
            

                
                

                    
                    

                        

                            CYP3A4 (Cytochrome P450 3A4)
                            Inhibitor
                        

                        
                        Primary Target
                        
                    

                    
                    

                        

                            CYP2D6 (Cytochrome P450 2D6)
                            Inhibitor
                        

                        
                    

                    
                

                
            


            
            

                
                

                    
                    
                        

                            

  
  Major


                            
                                Fluconazole + Rivaroxaban
                            
                        

                        
                        
Fluconazole markedly increases rivaroxaban exposure through dual inhibition of CYP3A4 and P-glycoprotein, substantially elevating bleeding risk.

                        
                    
                    
                    
                        

                            

  
  Major


                            
                                Fluconazole + Quetiapine
                            
                        

                        
                        
Fluconazole substantially increases quetiapine plasma concentrations via CYP3A4 inhibition, raising the risk of quetiapine-mediated QT prolongation and torsades de pointes.

                        
                    
                    
                    
                        

                            

  
  Major


                            
                                Fluconazole + Ondansetron
                            
                        

                        
                        
Fluconazole inhibits the metabolism of ondansetron and both drugs prolong the QT interval, creating a compounded arrhythmia risk.

                        
                    
                    
                    
                        

                            

  
  Major


                            
                                Fluconazole + Hydroxychloroquine
                            
                        

                        
                        
Fluconazole inhibits hydroxychloroquine metabolism and both drugs prolong the QT interval, creating compounded arrhythmia risk.

                        
                    
                    
                    
                        

                            

  
  Major


                            
                                Fluconazole + Warfarin
                            
                        

                        
                        
Fluconazole dramatically increases warfarin exposure, causing large INR elevations and a high risk of serious or life-threatening bleeding.

                        
                    
                    
                    
                        

                            

  
  Major


                            
                                Fluconazole + Tacrolimus
                            
                        

                        
                        
Fluconazole markedly inhibits CYP3A4-mediated tacrolimus metabolism, causing 2- to 4-fold elevations in tacrolimus trough levels and substantial risk of nephrotoxicity and neurotoxicity.

                        
                    
                    
                    
                        

                            

  
  Minor


                            
                                Fluconazole + Loratadine
                            
                        

                        
                        
Fluconazole inhibits CYP3A4-mediated metabolism of loratadine, modestly increasing loratadine plasma concentrations; however, loratadine's poor CNS penetration limits the clinical consequence.

                        
                    
                    
                    
                        

                            

  
  Minor


                            
                                Fluconazole + Pravastatin
                            
                        

                        
                        
Fluconazole has minimal effect on pravastatin exposure because pravastatin is not significantly metabolised by CYP enzymes; the interaction is pharmacokinetically unimportant in most patients.

                        
                    
                    
                    
                        

                            

  
  Minor


                            
                                Fluconazole + Montelukast
                            
                        

                        
                        
Fluconazole inhibits CYP2C8-mediated metabolism of montelukast, modestly increasing montelukast plasma concentrations; the clinical impact is generally minor given montelukast's wide therapeutic index.

                        
                    
                    
                    
                        

                            

  
  Moderate


                            
                                Fluconazole + Methylprednisolone
                            
                        

                        
                        
Fluconazole inhibits CYP3A4-mediated metabolism of methylprednisolone, increasing its plasma levels and prolonging corticosteroid effects, raising the risk of Cushingoid features.

                        
                    
                    
                    
                        

                            

  
  Moderate


                            
                                Fluconazole + Tamsulosin
                            
                        

                        
                        
Fluconazole inhibits CYP3A4-mediated tamsulosin metabolism, substantially increasing tamsulosin exposure and the risk of hypotension and syncope.

                        
                    
                    
                    
                        

                            

  
  Moderate


                            
                                Fluconazole + Sertraline
                            
                        

                        
                        
Fluconazole inhibits CYP2C19 and CYP3A4, increasing sertraline plasma concentrations, which may enhance both therapeutic and adverse effects including QT prolongation.

                        
                    
                    
                    
                        

                            

  
  Major


                            
                                Fluconazole + Apixaban
                            
                        

                        
                        
Fluconazole increases apixaban plasma concentrations significantly through dual CYP3A4 and P-gp inhibition, raising bleeding risk.

                        
                    
                    
                    
                        

                            

  
  Minor


                            
                                Fluconazole + Finasteride
                            
                        

                        
                        
Fluconazole inhibits CYP3A4, which contributes to finasteride metabolism; co-administration may modestly increase finasteride plasma concentrations, though the clinical significance is generally low.

                        
                    
                    
                    
                        

                            

  
  Moderate


                            
                                Fluconazole + Aripiprazole
                            
                        

                        
                        
Fluconazole inhibits CYP3A4 and CYP2C19, increasing aripiprazole plasma concentrations and the risk of aripiprazole adverse effects.

                        
                    
                    
                    
                        

                            

  
  Moderate


                            
                                Fluconazole + Dexamethasone
                            
                        

                        
                        
Fluconazole inhibits CYP3A4, reducing dexamethasone clearance and raising dexamethasone plasma levels, potentially causing Cushingoid features or adrenal suppression on steroid withdrawal.

                        
                    
                    
                

                
            


            
            

                
                


    
    
        
    
    
    
No side effects recorded

    
    
Side effect data is not yet available for this drug.

    



                
            


            
            
            

                
Часто задаваемые вопросы

                

                    
                    

                        
                        

                            
This antifungal medication works by blocking the production of ergosterol, an essential component of the fungal cell membrane, causing the organism to die. It is widely used to treat fungal infections including thrush, cryptococcal meningitis, and systemic candida infections.

                        

                    

                    

                    

                    
                    

                        
                        

                            
Inhibits fungal CYP51 (lanosterol 14-alpha-demethylase).

                        

                    

                    

                    
                    

                        
                        

                            
Key pharmacokinetic parameters for Fluconazole: Half-life: 30 hours.

                        

                    

                    

                    

                        
                        

                            
Yes, Fluconazole is an approved drug. It has reached clinical phase 4. It is classified as a Small molecule.

                        

                    

                

            

            

            
            

            
            
            

                
Related Drugs


                
                

                    
Same Drug Class

                    

                        
                        
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                            Small molecule
                        
                        
                        
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                            Small molecule
                        
                        
                        
                            Doxycycline
                            Small molecule
                        
                        
                    

                

                

                
                
                
            

            

            
            
{# References & Data Sources section for drug detail pages.
   Renders standard pharmacological database links plus the drug's data_sources field. #}


    
References & Data Sources

    
    
        
        
  • 
            
            
                ChEMBL — European Bioinformatics Institute (EBI).
                CHEMBL106.
                Open-access bioactivity database.
            
        
    • 
        
        
        
  • 
            
            
                PubChem — National Center for Biotechnology Information (NCBI).
                CID 3365.
                Chemical information database.
            
        
    • 
        
        
        
        
    

    
Data aggregated from publicly available pharmacological databases. Last updated 2026-03-04.




        


        
        
    


    



    
Медицинский отказ от ответственности

    

        This content is for educational and informational purposes only. It is not a substitute for professional medical advice, diagnosis, or treatment. Always consult a qualified healthcare provider before making medication decisions.
    

    

        Data sources:
        ChEMBL,
        PubChem,
        DailyMed.