Isoconazole

Identification

Name
Isoconazole
Accession Number
DB08943
Type
Small Molecule
Groups
Approved
Description

Isoconazole is an azole antifungal drug that has similar effectiveness to clotrimazole in the treatment of foot and vaginal infections.

Structure
Thumb
Synonyms
Not Available
International/Other Brands
Icaden (Bayer)
Categories
UNII
GRI7WFR424
CAS number
27523-40-6
Weight
Average: 416.129
Monoisotopic: 413.986023908
Chemical Formula
C18H14Cl4N2O
InChI Key
MPIPASJGOJYODL-UHFFFAOYSA-N
InChI
InChI=1S/C18H14Cl4N2O/c19-12-4-5-13(17(22)8-12)18(9-24-7-6-23-11-24)25-10-14-15(20)2-1-3-16(14)21/h1-8,11,18H,9-10H2
IUPAC Name
1-[2-(2,4-dichlorophenyl)-2-[(2,6-dichlorophenyl)methoxy]ethyl]-1H-imidazole
SMILES
ClC1=CC(Cl)=C(C=C1)C(CN1C=CN=C1)OCC1=C(Cl)C=CC=C1Cl

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AgmatineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Agmatine.
AlmasilateAlmasilate can cause a decrease in the absorption of Isoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
AloglutamolAloglutamol can cause a decrease in the absorption of Isoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
AluminiumAluminium can cause a decrease in the absorption of Isoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminium acetoacetateAluminium acetoacetate can cause a decrease in the absorption of Isoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminium glycinateAluminium glycinate can cause a decrease in the absorption of Isoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminium phosphateAluminium phosphate can cause a decrease in the absorption of Isoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Isoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.
AmiodaroneThe therapeutic efficacy of Isoconazole can be increased when used in combination with Amiodarone.
AmlodipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Amlodipine.
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patents 3,717,655; 3,839,574.

General References
  1. Czaika VA, Siebenbrock J, Czekalla F, Zuberbier T, Sieber MA: Reactive oxygen species and the bacteriostatic and bactericidal effects of isoconazole nitrate. Mycoses. 2013 May;56 Suppl 1:16-22. doi: 10.1111/myc.12055. [PubMed:23574020]
  2. Oyeka CA, Gugnani HC: Isoconazole nitrate versus clotrimazole in foot and nail infections due to Hendersonula toruloidea, Scytalidium hyalinum and dermatophytes. Mycoses. 1992 Nov-Dec;35(11-12):357-61. [PubMed:1302811]
  3. Veraldi S: Isoconazole nitrate: a unique broad-spectrum antimicrobial azole effective in the treatment of dermatomycoses, both as monotherapy and in combination with corticosteroids. Mycoses. 2013 May;56 Suppl 1:3-15. doi: 10.1111/myc.12054. [PubMed:23574019]
External Links
KEGG Drug
D04624
PubChem Compound
3760
PubChem Substance
310264910
ChemSpider
3629
BindingDB
31771
ChEBI
83667
ChEMBL
CHEMBL1571863
Wikipedia
Isoconazole
ATC Codes
G01AF07 — IsoconazoleD01AC05 — IsoconazoleG01AF20 — Combinations of imidazole derivatives

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)179U.S. Patents 3,717,655; 3,839,574.
Predicted Properties
PropertyValueSource
Water Solubility0.000825 mg/mLALOGPS
logP5.23ALOGPS
logP5.96ChemAxon
logS-5.7ALOGPS
pKa (Strongest Basic)6.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area27.05 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity103.07 m3·mol-1ChemAxon
Polarizability39.31 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-08fr-2900100000-a923b8a33f9c5abc906e

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzylethers
Direct Parent
Benzylethers
Alternative Parents
Dichlorobenzenes / N-substituted imidazoles / Aryl chlorides / Heteroaromatic compounds / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
Benzylether / 1,3-dichlorobenzene / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / N-substituted imidazole / Imidazole / Azole / Heteroaromatic compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
imidazoles, ether, dichlorobenzene (CHEBI:83667)

Drug created on May 26, 2014 16:37 / Updated on November 02, 2018 06:56