ECONAZOLE

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Synonyms
Status
Molecule Category UNKNOWN
ATC D01AC03 G01AF05
UNII 6Z1Y2V4A7M
EPA CompTox DTXSID2029872

Structure

InChI Key LEZWWPYKPKIXLL-UHFFFAOYSA-N
Smiles Clc1ccc(COC(Cn2ccnc2)c2ccc(Cl)cc2Cl)cc1
InChI
InChI=1S/C18H15Cl3N2O/c19-14-3-1-13(2-4-14)11-24-18(10-23-8-7-22-12-23)16-6-5-15(20)9-17(16)21/h1-9,12,18H,10-11H2

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H15Cl3N2O
Molecular Weight 381.69
AlogP 5.8
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 6.0
Polar Surface Area 27.05
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 24.0
Assay Description Organism Bioactivity Reference
Fold decrease in IC50 vs beta-lactamase on pre-incubation Escherichia coli 19.0
In vitro inhibition of human Cytochrome P450 17A1 activity Homo sapiens 325.0 nM
Fold increase in IC50 vs beta-lactamase with 1 mg/mL saponin Escherichia coli 50.0
Fold increase in IC50 vs beta-lactamase with 10x increased enzyme Escherichia coli 24.0
Inhibition of human CYP51 expressed in Topp 3 cells by lanosterol demethylase assay Homo sapiens 50.0 nM
Inhibition of CYP3A4 None 430.53 nM
Binding affinity to Mycobacterium smegmatis ATCC 700084 CYP51 at pH7.5 Mycobacterium smegmatis 880.0 nM
Binding affinity to Mycobacterium tuberculosis CYP51 Mycobacterium tuberculosis 200.0 nM
DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) None 636.0 nM
DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) None 379.0 nM
DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) None 296.0 nM
DRUGMATRIX: Opiate delta1 (OP1, DOP) radioligand binding (ligand: [3H] Naltrindole) None 508.0 nM
DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 423.0 nM DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 225.0 nM
DRUGMATRIX: Thromboxane Synthetase enzyme inhibition (substrate: PGH2) Homo sapiens 29.0 nM
DRUGMATRIX: CYP450, 1A2 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 300.0 nM
DRUGMATRIX: CYP450, 2C19 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 40.0 nM
DRUGMATRIX: CYP450, 2C9 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 200.0 nM
DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) None 400.0 nM
DRUGMATRIX: CYP450, 3A4 enzyme inhibition (substrate: 7-Benzyloxy-4-(trifluoromethyl)-coumarin) None 50.0 nM
DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) None 835.0 nM DRUGMATRIX: Dopamine Transporter radioligand binding (ligand: [125I] RTI-55) None 663.0 nM
Inhibition of mouse Tdo2 transfected in HEK293T cells using L-tryptophan as substrate assessed as kynurenine formation at 100 uM after 45 mins by spectrophotometric analysis relative to control Mus musculus 95.0 %
Inhibition of IDO1 (unknown origin) at highest soluble concentration using L-tryptophan substrate incubated for 60 mins by HPLC Homo sapiens 70.0 %
DNDI: Chagas in Vitro, 96 hour Trypanosoma cruzi 40.0 nM
DNDI: Malaria in Vitro, 72 hour Plasmodium falciparum 320.0 nM
Binding affinity to Mycobacterium tuberculosis H37Rv wild type CYP121 by titration assay Mycobacterium tuberculosis H37Rv 73.0 nM
Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria assessed as inhibition of mitochondrial respiration per mg mitochondrial protein measured for 20 mins by A65N-1 oxygen probe based fluorescence assay Rattus norvegicus 100.0 nM
Inhibition of CYP8B1 in human liver microsomes using D7-7alpha-hydroxy-4-cholesten-3-one as substrate preincubated for 20 mins followed by substrate addition in presence of NADPH by UPLC-ESI-MS/MS analysis Homo sapiens 310.0 nM
Inhibition of cytochrome P450 in Sprague-Dawley rat liver microsomes assessed as inhibition of NADPH-dependent retinoic acid oxidation at 10 uM incubated for 5 mins followed by retinoic acid addition and further incubated for 60 mins by HPLC analysis relative to control Rattus norvegicus 88.0 %
Inhibition of cytochrome P450 in Sprague-Dawley rat liver microsomes assessed as inhibition of NADPH-dependent retinoic acid oxidation at 100 uM incubated for 5 mins followed by retinoic acid addition and further incubated for 60 mins by HPLC analysis relative to control Rattus norvegicus 100.0 %
Inhibition of CYP3A4 (unknown origin) Homo sapiens 430.0 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 13.75 %
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 -0.31 % 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 -0.31 %

Related Entries

Cross References

Resources Reference
ChEBI 82873
ChEMBL CHEMBL808
DrugBank DB01127
DrugCentral 983
FDA SRS 6Z1Y2V4A7M
Human Metabolome Database HMDB0015259
Guide to Pharmacology 2446
KEGG C08068
PharmGKB PA164746010
PubChem 3198
SureChEMBL SCHEMBL34498
CONTENTS