Isoconazole

Identification

Summary

Isoconazole is an imidazole antifungal used for superficial skin and vaginal infections.

Generic Name
Isoconazole
DrugBank Accession Number
DB08943
Background

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

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 416.129
Monoisotopic: 413.986023908
Chemical Formula
C18H14Cl4N2O
Synonyms
  • Isoconazol
  • Isoconazole
  • Isoconazolum

Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatMixed vaginal infectionsCombination Product in combination with: Clindamycin (DB01190)•••••••••••••••••
Treatment ofSuperficial fungal skin infection••••••••••••••••••••• •••••
Treatment ofVulvovaginal fungal infections•••••••••••••••••• ••••••• •••••••••••
Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Isoconazole nitrate5AS8P3N30X24168-96-5NNGQLSIGRSTLLU-UHFFFAOYSA-N
International/Other Brands
Icaden (Bayer)
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
GYNO-TRAVOGEN OVULE 600 mgSuppository600 mgVaginalBAYER (SOUTH EAST ASIA) PTE LTD1989-05-26Not applicableSingapore flag
TRAVOGEN CREAM 1%Cream10 mg/gTopicalLEO PHARMA ASIA PTE LTD1991-01-14Not applicableSingapore flag
ทราโวเจน(R) ครีมCream1 %w/wTopicalบริษัท ดีเคเอสเอช (ประเทศไทย)2020-06-01Not applicableThailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ALBACORT % 1+% 0.1 KREM, 15 GIsoconazole nitrate (10 mg/g) + Difluocortolone valerate (1 mg/g)CreamTopicalKENTFARMA İLAÇ A.Ş.2018-03-27Not applicableTurkey flag
FUGGY % 0.1 + % 1 KREM, 15 GIsoconazole nitrate (1 %) + Difluocortolone valerate (0.1 %)CreamTopicalTRIPHARMA İLAÇ SAN. VE TİC. A.Ş.2019-09-13Not applicableTurkey flag
FUGGY % 0.1 + % 1 KREM, 30 GIsoconazole nitrate (1 %) + Difluocortolone valerate (0.1 %)CreamTopicalTRIPHARMA İLAÇ SAN. VE TİC. A.Ş.2019-09-13Not applicableTurkey flag
FUGİSİD %1 + %0,1 KREM, 15 GIsoconazole nitrate (1 %) + Difluocortolone valerate (0.1 %)CreamTopicalİSTANBUL İLAÇ SAN. VE TİC. A.Ş.2019-01-10Not applicableTurkey flag
FUNGOID %1+ %0,1 KREM, 15 GIsoconazole nitrate (1 %) + Difluocortolone (0.1 %)CreamTopicalSAĞLIK ÜRÜN VE HİZMETLERİ TİC. LTD. ŞTİ.2016-11-14Not applicableTurkey flag

Categories

ATC Codes
G01AF07 — IsoconazoleG01AF20 — Combinations of imidazole derivativesD01AC05 — Isoconazole
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,3-dichlorobenzene / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Azole / Benzylether / Chlorobenzene / Dialkyl ether / Ether
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
imidazoles, ether, dichlorobenzene (CHEBI:83667)
Affected organisms
Not Available

Chemical Identifiers

UNII
GRI7WFR424
CAS number
27523-40-6
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

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. [Article]
  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. [Article]
  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. [Article]
  4. INVIMA Product Authorization: Micofentin (isoconazole/clindamycin) vaginal cream [Link]
KEGG Drug
D04624
PubChem Compound
3760
PubChem Substance
310264910
ChemSpider
3629
BindingDB
31771
RxNav
27901
ChEBI
83667
ChEMBL
CHEMBL1571863
Wikipedia
Isoconazole

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionVaginal1 g/100g
TabletVaginal600 mg
CreamCutaneous1.000 g
CreamTopical
SuppositoryVaginal600 mg
CreamTopical1.000 g
CreamTopical1 g
CreamVaginal1 g
InsertVaginal600 mg
CreamVaginal100000 g
SolutionTopical1 g
CreamVaginal
InsertVaginal
Solution; sprayTopical1 %
Solution; sprayTopical
InsertVaginal0.6 g
CreamTopical
CreamTopical1 mg/g
CreamTopical1 %
CreamVaginal1 %
IrrigantVaginal0.1 %
CreamTopical10 mg/g
SprayTopical1 %
SprayTopical
InsertVaginal600.000 mg
CreamVaginal1.000 g
CreamTopical1 %w/w
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)6.48Chemaxon
Physiological Charge0Chemaxon
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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-01ot-2900000000-8ec386ee7fc11165aa32
MS/MS Spectrum - , positiveLC-MS/MSsplash10-08fr-2900100000-a923b8a33f9c5abc906e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0010900000-89296dbc4f842cbf7019
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-2102900000-4c1536fa7c42ea570035
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q0-7490600000-7949ec0a1746245d070c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9100000000-fd8de5bc3e69886ef19f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ap0-5921000000-1034e10da2a3c5ef3023
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9100000000-2b2de0864c31d97f01e9
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-179.02667
predicted
DeepCCS 1.0 (2019)
[M+H]+181.38467
predicted
DeepCCS 1.0 (2019)
[M+Na]+188.30606
predicted
DeepCCS 1.0 (2019)

Drug created at May 26, 2014 22:37 / Updated at June 12, 2021 10:54