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
Structured Indications
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
DrugInteractionDrug group
AmlodipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Isoconazole.Approved, Investigational
AmrinoneThe risk or severity of adverse effects can be increased when Isoconazole is combined with Amrinone.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Isoconazole is combined with Atorvastatin.Approved
AzelnidipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Azelnidipine.Approved, Investigational
AzimilideThe risk or severity of adverse effects can be increased when Isoconazole is combined with Azimilide.Investigational
BarnidipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Barnidipine.Approved
BencyclaneThe risk or severity of adverse effects can be increased when Isoconazole is combined with Bencyclane.Experimental
BenidipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Benidipine.Approved, Investigational
BepridilThe risk or severity of adverse effects can be increased when Isoconazole is combined with Bepridil.Approved, Withdrawn
BuspironeThe metabolism of Buspirone can be decreased when combined with Isoconazole.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Isoconazole.Approved, Investigational
CarboxyamidotriazoleThe risk or severity of adverse effects can be increased when Isoconazole is combined with Carboxyamidotriazole.Investigational
CaroverineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Caroverine.Experimental
CerivastatinThe risk or severity of adverse effects can be increased when Isoconazole is combined with Cerivastatin.Withdrawn
CilnidipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Cilnidipine.Approved, Investigational
CinnarizineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Isoconazole.Approved, Investigational, Withdrawn
ClevidipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Clevidipine.Approved
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Isoconazole.Approved, Investigational
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Isoconazole.Approved, Investigational, Vet Approved
DarodipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Darodipine.Experimental
DidanosineDidanosine can cause a decrease in the absorption of Isoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DiltiazemThe risk or severity of adverse effects can be increased when Isoconazole is combined with Diltiazem.Approved
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Isoconazole.Approved, Investigational
DofetilideThe metabolism of Dofetilide can be decreased when combined with Isoconazole.Approved
DotarizineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Dotarizine.Investigational
EfonidipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Efonidipine.Approved, Investigational
EperisoneThe risk or severity of adverse effects can be increased when Isoconazole is combined with Eperisone.Approved, Investigational
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Isoconazole.Approved
FelodipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Felodipine.Approved, Investigational
FendilineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Fendiline.Withdrawn
FlunarizineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Flunarizine.Approved
FluvastatinThe risk or severity of adverse effects can be increased when Isoconazole is combined with Fluvastatin.Approved
FosphenytoinThe serum concentration of Isoconazole can be decreased when it is combined with Fosphenytoin.Approved
GabapentinThe risk or severity of adverse effects can be increased when Isoconazole is combined with Gabapentin.Approved, Investigational
GallopamilThe risk or severity of adverse effects can be increased when Isoconazole is combined with Gallopamil.Investigational
IsradipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Isradipine.Approved
LacidipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Lacidipine.Approved, Investigational
LamotrigineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Lamotrigine.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Lercanidipine.Approved, Investigational
LidoflazineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Lidoflazine.Experimental
LosartanThe metabolism of Losartan can be decreased when combined with Isoconazole.Approved
LovastatinThe risk or severity of adverse effects can be increased when Isoconazole is combined with Lovastatin.Approved, Investigational
Magnesium SulfateThe risk or severity of adverse effects can be increased when Isoconazole is combined with Magnesium Sulfate.Approved, Vet Approved
ManidipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Manidipine.Approved, Investigational
MevastatinThe risk or severity of adverse effects can be increased when Isoconazole is combined with Mevastatin.Experimental
MibefradilThe risk or severity of adverse effects can be increased when Isoconazole is combined with Mibefradil.Investigational, Withdrawn
NaftopidilThe risk or severity of adverse effects can be increased when Isoconazole is combined with Naftopidil.Investigational
NicardipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Nicardipine.Approved
NifedipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Nifedipine.Approved
NiguldipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Niguldipine.Experimental
NiludipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Niludipine.Experimental
NilvadipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Nilvadipine.Approved, Investigational
NimesulideThe risk or severity of adverse effects can be increased when Isoconazole is combined with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Nimodipine.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Nitrendipine.Approved, Investigational
OtiloniumThe risk or severity of adverse effects can be increased when Isoconazole is combined with Otilonium.Experimental, Investigational
PerhexilineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Perhexiline.Approved, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Isoconazole.Approved, Vet Approved
PimozideIsoconazole may increase the arrhythmogenic activities of Pimozide.Approved
PinaveriumThe risk or severity of adverse effects can be increased when Isoconazole is combined with Pinaverium.Approved
PitavastatinThe risk or severity of adverse effects can be increased when Isoconazole is combined with Pitavastatin.Approved
PravastatinThe risk or severity of adverse effects can be increased when Isoconazole is combined with Pravastatin.Approved
PregabalinThe risk or severity of adverse effects can be increased when Isoconazole is combined with Pregabalin.Approved, Illicit, Investigational
PrenylamineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Prenylamine.Withdrawn
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Isoconazole.Approved, Vet Approved
QuinidineThe metabolism of Quinidine can be decreased when combined with Isoconazole.Approved
RanolazineThe metabolism of Ranolazine can be decreased when combined with Isoconazole.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Isoconazole.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Isoconazole.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Isoconazole.Approved
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Isoconazole.Approved, Investigational
RisedronateThe risk or severity of adverse effects can be increased when Isoconazole is combined with Risedronate.Approved, Investigational
RosuvastatinThe risk or severity of adverse effects can be increased when Isoconazole is combined with Rosuvastatin.Approved
SimvastatinThe risk or severity of adverse effects can be increased when Isoconazole is combined with Simvastatin.Approved
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Isoconazole.Approved
SucralfateSucralfate can cause a decrease in the absorption of Isoconazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Isoconazole.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Isoconazole.Approved, Investigational
TerodilineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Terodiline.Experimental
TetrahydropalmatineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Isoconazole is combined with Tolfenamic Acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Isoconazole is combined with Tranilast.Approved, Investigational
UbidecarenoneThe risk or severity of adverse effects can be increased when Isoconazole is combined with Ubidecarenone.Approved, Investigational, Nutraceutical
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Isoconazole.Approved
VerapamilThe risk or severity of adverse effects can be increased when Isoconazole is combined with Verapamil.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Vinpocetine.Investigational
XylometazolineThe risk or severity of adverse effects can be increased when Isoconazole is combined with Xylometazoline.Approved
ZiconotideThe risk or severity of adverse effects can be increased when Isoconazole is combined with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Isoconazole.Approved
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
D01AC05 — IsoconazoleG01AF07 — 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 December 01, 2017 16:11