VORICONAZOLE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC J02AC03
UNII JFU09I87TR
EPA CompTox DTXSID5046485

Structure

InChI Key BCEHBSKCWLPMDN-MGPLVRAMSA-N
Smiles C[C@@H](c1ncncc1F)[C@](O)(Cn1cncn1)c1ccc(F)cc1F
InChI
InChI=1S/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H14F3N5O
Molecular Weight 349.32
AlogP 2.18
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 76.72
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 25.0

Bioactivity

Mechanism of Action Action Reference
Cytochrome P450 51 inhibitor INHIBITOR DailyMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- - - - 25
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2A Cytochrome P450 2A6
- - - - 25
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2B Cytochrome P450 2B6
- 790-17500 - 340-400 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- 5250-8700 - 5100 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C8
- - - - 25
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- 3620-8400 - 2800 -
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- - - - 25
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 13000 - 660-2970 -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A5
- 2900 - 660-2970 -
Enzyme Cytochrome P450 Cytochrome P450 family 51 Cytochrome P450 family 51A Cytochrome P450 51A1
- - 423-429 - -
Enzyme Oxidoreductase
- 2900 - 660-2970 -
Enzyme
- 790-17500 423-429 340-400 25
Assay Description Organism Bioactivity Reference
Growth inhibition of Candida albicans ATCC 95020 at 0.2 to 25 mg/L Candida albicans 21.0 mm
Growth inhibition of Candida kefyr B11501 at 0.2 to 25 mg/L Kluyveromyces marxianus 23.0 mm
Growth inhibition of Candida albicans mutant DSY2621 at 0.2 to 25 mg/L Candida albicans 17.0 mm
Antifungal activity against Aspergillus fumigatus by broth microdilution method Aspergillus fumigatus 0.23 ug.mL-1
Antifungal activity against Aspergillus flavus by broth microdilution method Aspergillus flavus 0.23 ug.mL-1
Antifungal activity against Aspergillus terreus by broth microdilution method Aspergillus terreus 0.23 ug.mL-1
Antifungal activity against azole-sensitive Candida albicans by broth microdilution assay Candida albicans 0.007 ug.mL-1
Antifungal activity against azole-resistant Candida albicans by broth microdilution assay Candida albicans 4.0 ug.mL-1
Antifungal activity against azole-resistant Candida glabrata by broth microdilution assay Candida glabrata 8.0 ug.mL-1
Antifungal activity against azole-resistant Candida krusei by broth microdilution assay Pichia kudriavzevii 1.0 ug.mL-1
Antifungal activity against Aspergillus fumigatus isolate after 24 hrs by microbroth colorimetric XTT method Aspergillus fumigatus 2.34 ug.mL-1
Antifungal activity against Aspergillus flavus isolate after 24 hrs by microbroth colorimetric XTT method Aspergillus flavus 1.96 ug.mL-1
Antifungal activity against Aspergillus terreus isolate after 24 hrs by microbroth colorimetric XTT method Aspergillus terreus 11.69 ug.mL-1
Binding affinity to Candida albicans CYP56 by spectrophotometry Candida albicans 510.0 nM
Inhibition of CYP1A2 in human liver microsomes assessed as phenacetin O-deethylation at 100 uM after 30 mins Homo sapiens 25.0 %
Inhibition of CYP2A6 in human liver microsomes assessed as coumarin 7-hydroxylation at 100 uM after 15 mins Homo sapiens 25.0 %
Inhibition of CYP2C8 in human liver microsomes assessed as amodiquine N-deethylation at 100 uM after 15 mins Homo sapiens 25.0 %
Inhibition of CYP2D6 in human liver microsomes assessed as dextromethorphan O-demethylation at 100 uM after 30 mins Homo sapiens 25.0 %
Inhibition of CYP2B6 in human liver microsomes assessed as 8-hydroxyefavirenz 14-hydroxylation after 10 mins Homo sapiens 790.0 nM
Inhibition of CYP2B6 in human liver microsomes assessed as efavirenz 8-hydroxylation after 10 mins by Dixon plot analysis Homo sapiens 400.0 nM
Inhibition of CYP2B6 in human liver microsomes assessed as bupropion 4-hydroxylation after 15 mins by Dixon plot analysis Homo sapiens 340.0 nM
Competitive inhibition of CYP3A in human liver microsomes assessed as midazolam 4-hydroxylation after 5 mins by Dixon plot analysis Homo sapiens 660.0 nM
Inhibition of TxB2 production in human blood at 15 mg, po after 5 hrs by enzyme immunoassay pretreated with voriconazole at 400 mg, po every 12 hrs for 1 day and 200, po mg every 12 hrs for one additional day Homo sapiens 37.0 %
Inhibition of TxB2 production in human blood at 15 mg, po after 8 hrs by enzyme immunoassay pretreated with voriconazole at 400 mg, po every 12 hrs for 1 day and 200, po mg every 12 hrs for one additional day Homo sapiens 46.0 %
Inhibition of TxB2 production in human blood at 15 mg, po after 12 hrs by enzyme immunoassay pretreated with voriconazole at 400 mg, po every 12 hrs for 1 day and 200, po mg every 12 hrs for one additional day Homo sapiens 49.0 %
Inhibition of TxB2 production in human blood at 15 mg, po after 24 hrs by enzyme immunoassay pretreated with voriconazole at 400 mg, po every 12 hrs for 1 day and 200, po mg every 12 hrs for one additional day Homo sapiens 31.0 %
Inhibition of TxB2 production in human blood at 15 mg, po after 48 hrs by enzyme immunoassay pretreated with voriconazole at 400 mg, po every 12 hrs for 1 day and 200, po mg every 12 hrs for one additional day Homo sapiens 14.0 %
Binding affinity to Aspergillus fumigatus AF293 sterol 14-alpha demethylase isoenzyme B expressed in Escherichia coli Aspergillus fumigatus 423.0 nM
Binding affinity to Aspergillus fumigatus AF293 sterol 14-alpha demethylase isoenzyme B expressed in Escherichia coli assessed as tight binding affinity constant Aspergillus fumigatus 429.0 nM
Antitrypanosomal activity against amastigote stage of Trypanosoma cruzi infected in mouse NIH/3T3 cells after 48 hrs by Hoechst staining assay Trypanosoma cruzi 96.5 nM
Inhibition of CYP2B6 variant in human liver microsomes harboring CYP2B6*1/*1 genotype assessed as 8-hydroxyefavirenz formation using efavirenz as substrate after 15 mins by LC/MS/MS analysis Homo sapiens 400.0 nM
Inhibition of CYP2B6 variant in human liver microsomes harboring CYP2B6*6/*6 genotype assessed as 8-hydroxyefavirenz formation using efavirenz as substrate after 15 mins by LC/MS/MS analysis Homo sapiens 160.0 nM
Cytotoxicity against human MRC5 cells after 48 hrs by MTT assay Homo sapiens 40.0 ug.mL-1
Cytotoxicity against human MRC5 cells after 48 hrs by MTT assay Homo sapiens 40.0 ug.mL-1
Binding affinity to Candida albicans CYP51 by spectral titration method Candida albicans 165.0 nM
Binding affinity to Aspergillus fumigatus CYP51 by spectral titration method Aspergillus fumigatus 56.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -2.98 %
Cytotoxicity in human A549 cells assessed as reduction in cell viability at 0.08 uM/L incubated for 24 hrs by MTT assay relative to control Homo sapiens 17.1 %
Cytotoxicity in human A549 cells assessed as reduction in cell viability at 0.40 uM/L incubated for 24 hrs by MTT assay relative to control Homo sapiens 20.3 %
Cytotoxicity in human A549 cells assessed as reduction in cell viability at 2 uM/L incubated for 24 hrs by MTT assay relative to control Homo sapiens 25.5 %
Cytotoxicity in human A549 cells assessed as reduction in cell viability at 10 uM/L incubated for 24 hrs by MTT assay relative to control Homo sapiens 32.0 %
Cytotoxicity in human A549 cells assessed as reduction in cell viability at 50 uM/L incubated for 24 hrs by MTT assay relative to control Homo sapiens 36.7 %
Cytotoxicity against human HepG2 cells assessed as reduction in cell viability at 5 to 50 uM incubated for 24 hrs by XTT assay relative to control Homo sapiens 40.0 %
Binding affinity to full-length recombinant human CYP46A1 by spectral binding study Homo sapiens 50.0 nM
Inhibition of full-length recombinant human CYP46A1 assessed as reduction in cholesterol 24-hydroxylation using cholesterol as substrate in presence of NADPH cytochrome P450 oxidoreductase by gas chromatography-mass spectrometry Homo sapiens 22.0 nM Inhibition of full-length recombinant human CYP46A1 assessed as reduction in cholesterol 24-hydroxylation using cholesterol as substrate in presence of NADPH cytochrome P450 oxidoreductase by gas chromatography-mass spectrometry Homo sapiens 11.0 nM
Inhibition of full-length recombinant human CYP46A1 assessed as reduction in 25- and 27-hydroxylation of 24S-hydroxy cholesterol in presence of NADPH cytochrome P450 oxidoreductase by gas chromatography-mass spectrometry Homo sapiens 47.0 nM
In-vivo inhibition of CYP46A1 in C57/B6J mouse brain assessed as reduction in 24S-hydroxy cholesterol at 60 mg/kg, ip measured after 2 hrs by isotope dilution mass-spectrometry relative to control Mus musculus 20.0 %
In-vivo inhibition of CYP46A1 in C57/B6J mouse brain assessed as reduction in 24S-hydroxy cholesterol at 60 mg/kg, ip dosed qd for 5 days by isotope dilution mass-spectrometry relative to control Mus musculus 37.0 %
In-vivo inhibition of CYP46A1 in C57/B6J mouse plasma assessed as reduction in 24S-hydroxy cholesterol at 60 mg/kg, ip dosed qd for 5 days by isotope dilution mass-spectrometry relative to control Mus musculus 30.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 4.09 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 9.578 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.03 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.12 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.12 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.03 %

Environmental Exposure

Environmental Exposure Map
Countries
India

Cross References

Resources Reference
ChEBI 10023
ChEMBL CHEMBL638
DrugBank DB00582
DrugCentral 2846
FDA SRS JFU09I87TR
Human Metabolome Database HMDB0014720
KEGG C07622
PDB VOR
PharmGKB PA10233
PubChem 71616
SureChEMBL SCHEMBL36233
ZINC ZINC000000014864
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