ITRACONAZOLE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC J02AC02
UNII 304NUG5GF4

Structure

InChI Key VHVPQPYKVGDNFY-UHFFFAOYSA-N
Smiles CCC(C)n1ncn(-c2ccc(N3CCN(c4ccc(OCC5COC(Cn6cncn6)(c6ccc(Cl)cc6Cl)O5)cc4)CC3)cc2)c1=O
InChI
InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C35H38Cl2N8O4
Molecular Weight 705.65
AlogP 5.58
Hydrogen Bond Acceptor 12.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 11.0
Polar Surface Area 104.7
Molecular species NEUTRAL
Aromatic Rings 5.0
Heavy Atoms 49.0

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 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 33-700 - - 0-84
Enzyme Cytochrome P450 Cytochrome P450 family 51 Cytochrome P450 family 51A Cytochrome P450 51A1
- 3600 31 - -
Enzyme Protease Cysteine protease Cysteine protease CA clan Cysteine protease C1A family
- 3000 - - -
Enzyme
- 33-700 1010 - 0-84
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CC chemokine receptor
- 200-12589 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CXC chemokine receptor
- 100-20800 - - -
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Short peptide receptor (family A GPCR) Vasopressin and oxytocin receptor
- 794-12589 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - -
Transporter Primary active transporter ATP-binding cassette ABCB subfamily
- 18000-18000 - - 2
Assay Description Organism Bioactivity Reference
Inhibition of human cytochrome P450 3A4 None 700.0 nM
In vitro inhibition of Lanosterol 14-alpha demethylase (Candida albicans CY1005) Candida albicans 0.06 ug.mL-1
Inhibition of P-glycoprotein, mouse L-mdr1a expressed in LLC-PK1 epithelial cells using calcein-AM polarisation assay None 200.0 nM
Inhibition of P-glycoprotein, mouse L-mdr1b expressed in LLC-PK1 epithelial cells using calcein-AM polarisation assay None 700.0 nM
Inhibition of P-glycoprotein using calcein-AM assay transfected in porcine PBCEC None 30.0 nM
Inhibition of P-gp was determined using rhodamine-assay in human CaCo-2 cells None 2.0 %
Antagonist activity at hedgehog receptor None 800.0 nM
Binding affinity to Candida albicans CYP56 by spectrophotometry Candida albicans 100.0 nM
PUBCHEM_BIOASSAY: Luminescence Cell-Based/Microorganism Dose Confirmation HTS to Identify Inhibitors of Trypanosoma cruzi Replication. (Class of assay: confirmatory) [Related pubchem assays: 1885, 1968 ] None 100.0 nM
Binding affinity to Mycobacterium smegmatis ATCC 700084 CYP164A2 at pH7.5 Mycobacterium smegmatis 780.0 nM
Antifungal activity against 5 x 10'6 CFU/ml Trichophyton mentagrophytes B70554 by resazurin based fluorimetry assay Trichophyton mentagrophytes 370.0 nM
Antifungal activity against 5 x 10'6 CFU/ml Trichophyton rubrum B68183 by resazurin based fluorimetry assay Trichophyton rubrum 560.0 nM
Antifungal activity against 5 x 10'6 CFU/ml Trichophyton rubrum J941704 by resazurin based fluorimetry assay Trichophyton rubrum 980.0 nM
Antifungal activity against 5 x 10'6 CFU/ml Candida kefyr B46120 by resazurin based fluorimetry assay Kluyveromyces marxianus 400.0 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 31.0 nM
DRUGMATRIX: CYP450, 3A4 enzyme inhibition (substrate: 7-Benzyloxy-4-(trifluoromethyl)-coumarin) None 900.0 nM
Fungistatic activity against Saccharomyces cerevisiae ATCC 24657 assessed as cell proliferation at 90.7 uM after 24 hrs by agar plate bioassay relative to control Saccharomyces cerevisiae 95.0 %
TP_TRANSPORTER: inhibition of Calcein-AM efflux in Mdr1a-expressing LLC-PK1 cells None 200.0 nM
TP_TRANSPORTER: inhibition of Calcein-AM efflux in Mdr1b-expressing LLC-PK1 cells None 700.0 nM
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 22.3 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens -2.3 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 59.8 %
Inverse agonist activity at CCR4 in human HTLA cells assessed as depression of basal activity incubated for 20 mins by beta arrestin-recruitment mediated luciferase reporter gene assay in absence of CCL22 Homo sapiens 200.0 nM
Inhibition of vasopressin-stimulated vasopressin V2 receptor in human HTLA cells pre-incubated for 20 mins measured on day 4 by beta arrestin-recruitment mediated luciferase reporter gene assay Homo sapiens 800.0 nM Inhibition of vasopressin-stimulated vasopressin V2 receptor in human HTLA cells pre-incubated for 20 mins measured on day 4 by beta arrestin-recruitment mediated luciferase reporter gene assay Homo sapiens 794.33 nM
Inhibition of CX3CL1-stimulated CX3CR1 in human HTLA cells pre-incubated for 20 mins measured on day 4 by beta arrestin-recruitment mediated luciferase reporter gene assay Homo sapiens 100.0 nM Inhibition of CX3CL1-stimulated CX3CR1 in human HTLA cells pre-incubated for 20 mins measured on day 4 by beta arrestin-recruitment mediated luciferase reporter gene assay Homo sapiens 158.49 nM
Inhibition of CCL22-stimulated CCR4 in human HTLA cells pre-incubated for 20 mins measured on day 4 by beta arrestin-recruitment mediated luciferase reporter gene assay Homo sapiens 500.0 nM Inhibition of CCL22-stimulated CCR4 in human HTLA cells pre-incubated for 20 mins measured on day 4 by beta arrestin-recruitment mediated luciferase reporter gene assay Homo sapiens 501.19 nM
Cytotoxicity against african green monkey Vero cells after 48 hrs by MTT assay Chlorocebus sabaeus 50.0 ug.mL-1
Cytotoxicity against human A549 cells after 48 hrs by MTT assay Homo sapiens 182.0 ug.mL-1
Cytotoxicity against human HT1080 cells after 48 hrs by MTT assay Homo sapiens 201.63 ug.mL-1
Cytotoxicity against human HepG2 cells after 48 hrs by MTT assay Homo sapiens 142.0 ug.mL-1
Antiproliferative activity against mouse medulloblastoma cells expressing wild type SMO Mus musculus 55.0 nM
Inhibition of CYP3A4 in human hepatocytes using testosterone as substrate by HPLC/MS/MS method Homo sapiens 70.0 nM
DNDI: Chagas in Vitro, 96 hour Trypanosoma cruzi 4.0 nM
Inhibition of CYP3A4.1 (unknown origin)-mediated testosterone 6beta-hydroxylation incubated for 10 mins prior to NADPH addition measured after 20 mins by HPLC-UV analysis Homo sapiens 76.0 nM
Inhibition of CYP3A4.2 (unknown origin)-mediated testosterone 6beta-hydroxylation incubated for 10 mins prior to NADPH addition measured after 20 mins by HPLC-UV analysis Homo sapiens 45.0 nM
Inhibition of CYP3A4.7 (unknown origin)-mediated testosterone 6beta-hydroxylation incubated for 10 mins prior to NADPH addition measured after 20 mins by HPLC-UV analysis Homo sapiens 179.0 nM
Inhibition of CYP3A4.16 (unknown origin)-mediated testosterone 6beta-hydroxylation incubated for 10 mins prior to NADPH addition measured after 20 mins by HPLC-UV analysis Homo sapiens 41.0 nM
Inhibition of CYP3A4.18 (unknown origin)-mediated testosterone 6beta-hydroxylation incubated for 10 mins prior to NADPH addition measured after 20 mins by HPLC-UV analysis Homo sapiens 82.0 nM
Inhibition of hedgehog pathway in mouse C3H10T1/2 cells assessed as downregulation of Gli1 mRNA expression after 24 hrs by qPCR method Mus musculus 63.0 nM
Inhibition of hedgehog pathway in mouse ASZ cells assessed as downregulation of Gli1 mRNA expression after 48 hrs by qPCR method Mus musculus 140.0 nM
Inhibition of CYP3A4 in human liver microsomes using testosterone as substrate after 10 mins by LC/MS/MS analysis Homo sapiens 50.4 nM
Inhibition of hedgehog pathway in mouse MERP MB cells assessed as downregulation of Gli1 mRNA expression after 48 hrs by qPCR method Mus musculus 390.0 nM
Inhibition of hedgehog pathway in mouse Shh-Light2 cells after 46 hrs by luciferase reporter gene assay Mus musculus 690.0 nM
Antiproliferative activity against HUVEC assessed as inhibition of VEGF induced cell proliferation using methyl-[3H]thymidine after 36 hrs Homo sapiens 160.0 nM
Inhibition of Orai1-mediated store operated Ca2+ entry in human MDA-MB-231 cells assessed as reduction of SERCA inhibition-induced ER release at 100 uM preincubated for 15 mins followed by CPA addition by PBX-based FLIPR assay Homo sapiens 10.0 %
Inhibition of Orai1-mediated store operated Ca2+ entry in human MDA-MB-231 cells assessed as reduction in BAPTA-induced Ca2+ depletion-stimulated SOCE activity at 100 uM preincubated for 15 mins followed by BAPTA addition in presence of extracellular Ca2+ by PBX-based FLIPR assay relative to control Homo sapiens 10.0 %
Inhibition of CYP3A4 in human liver microsomes assessed as reduction in nifedipine oxidation incubated for 10 mins Homo sapiens 32.6 nM
Antileishmanial activity against wild type Leishmania major LV39 Rho/SU/59/P promastigote forms after 48 hrs Leishmania major 400.0 nM
Antileishmanial activity against Leishmania major LV39 Rho/SU/59/P promastigote forms harboring c14dm-/+C14DM mutant after 48 hrs Leishmania major 400.0 nM
Anti-angiogenic activity against HUVEC after 24 hrs by scintillation counting based [3H]-thymidine incorporation assay Homo sapiens 170.0 nM
Inhibition of human liver microsome CYP3A4 at 1 uM expressed in baculosomes using fluorogenic-DBOMF as substrate preincubated for 10 mins followed by substrate addition and measured after 60 mins by fluorescence based assay Homo sapiens 84.0 %
Antiangiogenic activity in HUVEC assessed as inhibition of tube formation at 5 uM after 24 hrs by matrigel assay relative to control Homo sapiens 45.0 %
Inhibition of Smo-mediated hedgehog signaling pathway in mouse Light2 cells in Shh conditioned medium after 48 hrs by Gli-Renilla luciferase reporter gene assay Mus musculus 690.0 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 -4.93 %
Inhibition of Hedgehog signaling pathway in mouse ASZ001 cells assessed as decrease in Gli1 mRNA expression after 48 hrs by qRT-PCR analysis Mus musculus 140.0 nM
Inhibition of mouse Smo A1 mutant expressed in mouse Shh Light2 cells assessed as reduction in hedgehog pathway activation incubated for 30 hrs by luminescence assay Mus musculus 800.0 nM
Inhibition of CYP3A4 in human liver microsomes by LC-MS/MS analysis Homo sapiens 40.0 nM
Inhibition of human ERG expressed in CHO cells at 25 uM by electrophysiology assay relative to control Homo sapiens 1.0 %
Inhibition of human ERG Homo sapiens 1.0 %
Inhibition of CYP3A4 (unknown origin) using midazolam as substrate by UPLC-MS/MS analysis Homo sapiens 0.04 %
Antifungal activity against Histoplasma capsulatum G217B after 10 to 14 days by microscopic method Histoplasma capsulatum 0.001 ug.mL-1
Antileishmanial activity against Leishmania amazonensis MHOM/BR/75/Josefa promastigotes assessed as reduction in parasite viability after 72 hrs by Neubauer chamber counting method Leishmania amazonensis 440.0 nM
Antileishmanial activity against Leishmania amazonensis MHOM/BR/75/Josefa intracellular amastigotes infected in CF-1 macrophages assessed as reduction in parasite viability after 72 hrs by optical microscopic method Leishmania amazonensis 80.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 12.23 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 2.535 %
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 8.0 % 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 8.0 % 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 %
Inhibition of Hedgehog signaling pathway in mouse ASZ001 cells assessed as decrease in Gli1 mRNA expression after 48 hrs by qRT-PCR analysis Mus musculus 140.0 nM
Inhibition of NPC1/VDAC1 in HUVEC cells assessed as reduction in cell proliferation pretreated for 24 hrs followed by [3H]thymidine incorporation by scintillation counter method Homo sapiens 170.0 nM
Inhibition of CYP3A4 in human liver microsome using Nifedipine as a substrate incubated for 10 mins in the presence of NADPH by LC-MS/MS analysis Homo sapiens 32.6 nM

Related Entries

Cross References

Resources Reference
ChEBI 94366
ChEMBL CHEMBL64391
DrugCentral 1513
FDA SRS 304NUG5GF4
PubChem 55283
SureChEMBL SCHEMBL16984893
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