Drug Details

General Information of the Drug (ID: DR6366)
Name
Fluconazole
Synonyms
fluconazole; 86386-73-4; Diflucan; Triflucan; Biozolene; Elazor; Biocanol; Fluconazol; Fungata; Fluconazolum; Flucostat; 2-(2,4-DIFLUOROPHENYL)-1,3-DI(1H-1,2,4-TRIAZOL-1-YL)PROPAN-2-OL; UK 49858; Flusol; Zoltec; 2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol; UK-49858; 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol; C13H12F2N6O; UNII-8VZV102JFY; 1H-1,2,4-Triazole-1-ethanol, alpha-(2,4-difluorophenyl)-alpha-(1H-1,2,4-triazol-1-ylmethyl)-; Pritenzol; Flucazol; Flukezol; Flunizol; Zonal; CHEMBL106; 2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)-2-propanol; 8VZV102JFY; 2,4-Difluoro-alpha,alpha-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcohol; alpha-(2,4-Difluorophenyl)-alpha-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol; Alflucoz; Cryptal; Dimycon; Oxifugol; Canzol; CHEBI:46081; Forcan; Syscan; Baten; Mutum; Zemyc; 2-(2,4-Difluorophenyl)-1,3-di-1H-1,2,4-triazol-1-ylpropan-2-ol; Fluconazole, 98%; MFCD00274549; difluconazole; NCGC00095089-01; Flunazol; Fluconazol [Spanish]; Fluconazolum [Latin]; Loitin; UK-49,858; DSSTox_CID_627; DSSTox_RID_75701; DSSTox_GSID_20627; FLC; DRG-0005; Diflazon; Fuconal; Triconal; Trican; Diflucan (TN); SMR000471882; CAS-86386-73-4; FLCZ; CCRIS 7211; Fluconazole & hGCSF; DIFLUCAN IN SODIUM CHLORIDE 0.9%; HSDB 7420; SR-01000765440; Fluconazole in sodium chloride 0.9%; DIFLUCAN IN DEXTROSE 5% IN PLASTIC CONTAINER; Flucoral; 2-(2,4-difluorophenyl)-1,3-di(1,2,4-triazolyl)propan-2-ol; Fluconazole & MC-510,011; Fluconazole (f); Fluconazole,(S); Fluconazole in dextrose 5% in plastic container; 2,4-Difluoro-alpha,alpha-1-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcohol; Fluzon [Antifungal]; Fluconazole [USAN]; KS-1059; Fluconazole [USAN:USP:INN:BAN:JAN]; Fluconazole in sodium chloride 0.9% in plastic container; Fluconazole in combination with MGCD290; Spectrum_001654; DIFLUCAN IN SODIUM CHLORIDE 0.9% IN PLASTIC CONTAINER; Spectrum2_001607; Spectrum3_001912; Spectrum4_000090; Spectrum5_001277; F0677; MGCD290 and Fluconazole; cid_3365; MG-3290 and Fluconazole; SCHEMBL3151; BSPBio_003504; KBioGR_000360; KBioSS_002134; 123631-92-5; MLS001066394; MLS001165780; MLS001195645; MLS001304713; MLS001306492; MLS006011884; BIDD:GT0799; DivK1c_001030; SPECTRUM1503975; SPBio_001613; ZINC4009; Fluconazole (JP17/USP/INN); DTXSID3020627; BDBM25817; HMS503M21; KBio1_001030; KBio2_002134; KBio2_004702; KBio2_007270; KBio3_003009; NINDS_001030; BAYT006267; HMS1922O10; HMS2090I20; HMS2093M21; HMS2230O22; HMS3259H13; HMS3373I19; HMS3654P15; HMS3715F21; HMS3748G19; Pharmakon1600-01503975; AMY23415; BAYT-006267; BCP28522; Fluconazole 2.0 mg/ml in Methanol; HY-B0101; 1,2,4-triazol-1-yl)propan-2-ol; Tox21_111419; Tox21_202240; Tox21_300581; 2-(2,4-Difluoro-phenyl)-1,3-bis-[1,2,4]triazol-1-yl-propan-2-ol; ABP001077; AC-428; ANW-42860; BBL005614; CCG-39065; CF0055; DL-407; Fluconazole & Human recombinant granulocyte colony stimulating factor; KM2402; NSC754343; NSC758661; s1331; SBB066063; STK619301; AKOS000280854; Tox21_111419_1; CS-1835; DB00196; Fluconazole, >=98% (HPLC), powder; MCULE-8641424658; NC00650; NSC 758661; NSC-754343; NSC-758661; IDI1_001030; NCGC00095089-02; NCGC00095089-04; NCGC00095089-05; NCGC00095089-06; NCGC00095089-07; NCGC00095089-08; NCGC00095089-09; NCGC00095089-10; NCGC00095089-11; NCGC00254412-01; NCGC00259789-01; 2-(2,4-difluorophenyl)-1,3-di(1H-; Fluconazole 100 microg/mL in Acetonitrile; SBI-0051880.P002; AB0008515; UK-049858; FT-0626437; ST51039043; SW199616-2; EN300-53634; C07002; D00322; J10407; AB00052399-07; AB00052399-08; AB00052399_09; AB00052399_10; 386F734; A841625; Q411478; 3-[4-(pyrrolidin-1-ylsulfonyl)phenyl]propanoicacid; Q-201120; SR-01000765440-2; SR-01000765440-4; SR-01000765440-8; UK-49858;UK 49858;UK49858; BRD-K05977355-001-02-6; BRD-K05977355-001-09-1; F2173-0496; Z235354561; Fluconazole, European Pharmacopoeia (EP) Reference Standard; 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)-2-propanol; Fluconazole, United States Pharmacopeia (USP) Reference Standard; 2-[2,4-bis(fluoranyl)phenyl]-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol; Fluconazole, Pharmaceutical Secondary Standard; Certified Reference Material; Fluconazole for peak identification, European Pharmacopoeia (EP) Reference Standard; Fluconazole solution, 2.0 mg/mL in methanol, ampule of 1 mL, certified reference material; .alpha.-(2,4-Difluorophenyl)-.alpha.-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol
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Molecular Type
Small molecule
Disease Fungal infection [ICD-11: 1F29-1F2F] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C13H12F2N6O
PubChem CID
3365
Canonical SMILES
C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O
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
InChIKey
RFHAOTPXVQNOHP-UHFFFAOYSA-N
CAS Number
CAS 86386-73-4
ChEBI ID
CHEBI:46081
TTD Drug ID
D09LNI
DrugBank ID
DB00196
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Alpinia purpurata lectin      Alpinia purpurata     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Staphylococcus aureus Microorganism model Staphylococcus aureus
Pseudomonas aeruginosa Microorganism model Pseudomonas aeruginosa
                    Experimental
                    Result(s)		 ApuL-oxacillin combination showed synergistic effect on the oxacillin-resistant isolates UFPEDA-670 and 671, which were not sensitive to lectin alone.
          Beta lapachone      Tabebuia avellanedae     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Candida albicans Microorganism model Candida albicans
                    Experimental
                    Result(s)		 Beta-lapachone reverted antifungal resistance of S. cerevisiae and C. albicans strains overexpressing CaCdr2p and CaMdr1p transporters by inhibiting these proteins activities. CaCdr2p ATPase activity was not impaired by the compound.
          Farnesol      Mosla chinensis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Expression FDFT1  Molecule Info 
Pathway MAP
                    In-vitro Model Candida albicans SC5314 Microorganism model Candida albicans
                    Experimental
                    Result(s)		 FAR and FAR/FLC affected fitness of C. albicans biofilm and the ERG gene regulation.
          Glycyrol      Glycyrrhiza uralensis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Mouse was shaved with electric clippers and an approximately 4 cm2 area was marked and slightly abraded with sterile sandpaper before infection with 20 ul of suspension containing 1*106 C. albicans.
                    Experimental
                    Result(s)		 It is very likely that, by damaging the cell wall, glycyrol helps fluconazole invade C. albicans more readily and attack fluconazole's target in the fungus membrane.
          N-butylphthalide      Apium graveolens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression BICDL1  Molecule Info 
Pathway MAP
Down-regulation Expression BICDL2  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Up-regulation ROS accumulation
                    In-vitro Model Candida albicans Microorganism model Candida albicans
                    Experimental
                    Result(s)		 The synergistic effects between n-butylphthalide and fluconazole potentially relied on the mechanism that n-butylphthalide significantly promoted drug uptake, and suppressed drug efflux via down-regulating the drug transporter encoding genes CDR1 and CDR2.
    β. A List of Natural Product(s) Able to Reverse the Resistance of This Drug
          Alpinia purpurata lectin      Alpinia purpurata     Click to Show/Hide the Molecular Data of This NP
                 Reversing Drug Resistance     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Pseudomonas aeruginosa UFPEDA-416 Microorganism model Pseudomonas aeruginosa
Pseudomonas aeruginosa UFPEDA-02 Microorganism model Pseudomonas aeruginosa
                    Experimental
                    Result(s)		 ApuL showed synergistic action in combination with antibiotics.
Target and Pathway
Target(s) Candida Cytochrome P450 51 (Candi ERG11)  Molecule Info  [7]
References
Reference 1 Fluconazole use as an important risk factor in the emergence of fluconazole-resistant Candida glabrata fungemia. Arch Intern Med. 2009 Aug 10;169(15):1444-5; author reply 1445.
Reference 2 Antimicrobial potential of Alpinia purpurata lectin (ApuL): Growth inhibitory action, synergistic effects in combination with antibiotics, and antibiofilm activity. Microb Pathog. 2018 Nov;124:152-162.
Reference 3 Synergistic interactions between Beta-lapachone and fluconazole in the inhibition of CaCdr2p and CaMdr1p in Candida albicans. Rev Iberoam Micol. Jul-Oct 2020;37(3-4):104-106.
Reference 4 The impact of farnesol in combination with fluconazole on Candida albicans biofilm: regulation of ERG20, ERG9, and ERG11 genes. Folia Microbiol (Praha). 2018 May;63(3):363-371.
Reference 5 Synergic effect of combination of glycyrol and fluconazole against experimental cutaneous candidiasis due to Candida albicans. Arch Pharm Res. 2016 Oct;39(10):1482-1489.
Reference 6 Antifungal Activity and Potential Mechanism of N-Butylphthalide Alone and in Combination With Fluconazole Against Candida albicans. Front Microbiol. 2019 Jul 2;10:1461.
Reference 7 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
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