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
DrugInteractionDrug group
AgmatineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Agmatine.Experimental, Investigational
AmiodaroneThe therapeutic efficacy of Isoconazole can be increased when used in combination with Amiodarone.Approved, Investigational
AmlodipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Isoconazole.Approved, Investigational
AmrinoneThe therapeutic efficacy of Isoconazole can be increased when used in combination with Amrinone.Approved
AranidipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Aranidipine.Approved, Investigational
AtorvastatinThe risk or severity of myopathy can be increased when Isoconazole is combined with Atorvastatin.Approved
AzelnidipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Azelnidipine.Approved, Investigational
AzimilideThe therapeutic efficacy of Isoconazole can be increased when used in combination with Azimilide.Investigational
BarnidipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Barnidipine.Approved
BencyclaneThe therapeutic efficacy of Isoconazole can be increased when used in combination with Bencyclane.Experimental
BenidipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Benidipine.Approved, Investigational
BepridilThe therapeutic efficacy of Isoconazole can be increased when used in combination with Bepridil.Approved, Withdrawn
BioallethrinThe therapeutic efficacy of Isoconazole can be increased when used in combination with Bioallethrin.Approved, Experimental
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 therapeutic efficacy of Isoconazole can be increased when used in combination with Carboxyamidotriazole.Investigational
CaroverineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Caroverine.Experimental
CilnidipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Cilnidipine.Approved, Investigational
CinnarizineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Isoconazole.Approved, Investigational, Withdrawn
ClevidipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Clevidipine.Approved, Investigational
CyclandelateThe therapeutic efficacy of Isoconazole can be increased when used in combination with Cyclandelate.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Isoconazole.Approved, Investigational, Vet Approved
DarodipineThe therapeutic efficacy of Isoconazole can be increased when used in combination 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 therapeutic efficacy of Isoconazole can be increased when used in combination with Diltiazem.Approved, Investigational
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Isoconazole.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Isoconazole.Approved, Investigational
DotarizineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Dotarizine.Investigational
EfonidipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Efonidipine.Approved, Investigational
EperisoneThe therapeutic efficacy of Isoconazole can be increased when used in combination with Eperisone.Approved, Investigational
EthosuximideThe therapeutic efficacy of Isoconazole can be increased when used in combination with Ethosuximide.Approved
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Isoconazole.Approved
FelodipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Felodipine.Approved, Investigational
FendilineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Fendiline.Withdrawn
Fish oilThe therapeutic efficacy of Isoconazole can be increased when used in combination with Fish oil.Approved, Nutraceutical
FlunarizineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Flunarizine.Approved
FluspirileneThe therapeutic efficacy of Isoconazole can be increased when used in combination with Fluspirilene.Approved, Investigational
FosphenytoinThe serum concentration of Isoconazole can be decreased when it is combined with Fosphenytoin.Approved, Investigational
GabapentinThe therapeutic efficacy of Isoconazole can be increased when used in combination with Gabapentin.Approved, Investigational
GallopamilThe therapeutic efficacy of Isoconazole can be increased when used in combination with Gallopamil.Investigational
IsradipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Isradipine.Approved, Investigational
LacidipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Lacidipine.Approved, Investigational
LamotrigineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Lamotrigine.Approved, Investigational
LercanidipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Lercanidipine.Approved, Investigational
LevetiracetamThe therapeutic efficacy of Isoconazole can be increased when used in combination with Levetiracetam.Approved, Investigational
LidoflazineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Lidoflazine.Experimental
LoperamideThe therapeutic efficacy of Isoconazole can be increased when used in combination with Loperamide.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Isoconazole.Approved
Magnesium sulfateThe therapeutic efficacy of Isoconazole can be increased when used in combination with Magnesium sulfate.Approved, Investigational, Vet Approved
ManidipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Manidipine.Approved, Investigational
MentholThe therapeutic efficacy of Isoconazole can be increased when used in combination with Menthol.Approved
MethsuximideThe therapeutic efficacy of Isoconazole can be increased when used in combination with Methsuximide.Approved
MibefradilThe therapeutic efficacy of Isoconazole can be increased when used in combination with Mibefradil.Investigational, Withdrawn
NaftopidilThe therapeutic efficacy of Isoconazole can be increased when used in combination with Naftopidil.Investigational
NicardipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Nicardipine.Approved, Investigational
NifedipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Nifedipine.Approved
NiguldipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Niguldipine.Experimental
NiludipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Niludipine.Experimental
NilvadipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Isoconazole can be increased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Nimodipine.Approved, Investigational
NisoldipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Nisoldipine.Approved
NitrendipineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Nitrendipine.Approved, Investigational
NylidrinThe therapeutic efficacy of Isoconazole can be increased when used in combination with Nylidrin.Approved
OtiloniumThe therapeutic efficacy of Isoconazole can be increased when used in combination with Otilonium.Experimental, Investigational
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Isoconazole.Approved, Vet Approved
PinaveriumThe therapeutic efficacy of Isoconazole can be increased when used in combination with Pinaverium.Approved
PrenylamineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Prenylamine.Withdrawn
ProgesteroneThe absorption of Progesterone can be decreased when combined with Isoconazole.Approved, Vet Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Isoconazole.Approved, Investigational
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Isoconazole.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Isoconazole.Approved, Investigational
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, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Isoconazole.Approved, Investigational
SeletracetamThe therapeutic efficacy of Isoconazole can be increased when used in combination with Seletracetam.Investigational
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 therapeutic efficacy of Isoconazole can be increased when used in combination with Terodiline.Experimental
TetrahydropalmatineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Isoconazole can be increased when used in combination with Tolfenamic Acid.Approved, Investigational
TranilastThe therapeutic efficacy of Isoconazole can be increased when used in combination with Tranilast.Approved, Investigational
TrimebutineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Trimebutine.Approved
TrimethadioneThe therapeutic efficacy of Isoconazole can be increased when used in combination with Trimethadione.Approved
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Isoconazole.Approved
VerapamilThe therapeutic efficacy of Isoconazole can be increased when used in combination with Verapamil.Approved
VinpocetineThe therapeutic efficacy of Isoconazole can be increased when used in combination with Vinpocetine.Investigational
WIN 55212-2The therapeutic efficacy of Isoconazole can be increased when used in combination with WIN 55212-2.Experimental
ZiconotideThe therapeutic efficacy of Isoconazole can be increased when used in combination with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Isoconazole.Approved
ZonisamideThe therapeutic efficacy of Isoconazole can be increased when used in combination with Zonisamide.Approved, Investigational
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 July 02, 2018 19:09