Clotrimazole (CED0003239)

Record Information
Version1.0
Creation Date2009-07-21 20:26:25 UTC
Update Date2026-05-14 16:24:59 UTC
Accession NumberCHEM002155
Identification
Common NameClotrimazole
ClassSmall Molecule
Description
Clotrimazole belongs to the triphenyl compounds, a class of benzenoids within the organic compounds. This exogenous compound has the formula C22H17ClN2 and an average molecular weight of 344.84 g/mol. At room temperature, it exists as a solid. It functions as an antiinfective agent, fungicide (PMC10416055, PMC3133525), antifungal agent (PMC4464443), and biological inhibitor (PMC10416055, PMC3133525), and it is used industrially as a biocide and anti-dandruff agent (PMC10416055, PMC3133525). The compound has been detected in skin tissue. It interacts with yeast 14-α demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential membrane component. This interaction inhibits ergosterol synthesis, leading to increased cellular permeability. Additionally, clotrimazole may impair triglyceride and/or phospholipid biosynthesis, inhibit the uptake of purine, inhibit the transformation of yeasts to mycelial forms, interact with membrane phospholipids, and inhibit endogenous respiration. Among its protein targets, it acts as an antagonist to the intermediate conductance calcium-activated potassium channel protein 4 (KCNN4) and serves as an inhibitor, modulator, or partial agonist of the Aryl hydrocarbon receptor (AHR), Estrogen receptor (ESR1), Hypoxia-inducible factor 1-alpha (HIF1A), and Nuclear receptor subfamily 1 group I member 2 (NR1I2), among 17 other proteins. Clotrimazole is found in 24 recorded sources, including healthcare, pharmaceuticals, and veterinary products such as antibiotics, gynecologicals, stomatological preparations, and antifungals for dermatological use. Other sources include food processing, drinking water, building and construction floors, household cleaning and consumer products, and electrical and electronic equipment. Recorded exposure routes include vaginal, topical, oral, inhalation, and extracorporeal.
Contaminant Type
  • 14-alpha Demethylase Inhibitor
  • Amine
  • Anti-Infective Agent, Local
  • Antifungal Agent
  • Drug
  • Food Toxin
  • Growth Inhibitor
  • Metabolite
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
SynonymsNot Available
Chemical FormulaC22H17ClN2
Average Molecular Mass344.837 g/mol
Monoisotopic Mass344.108 g/mol
CAS Registry Number23593-75-1
IUPAC Name1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole
Traditional Nameclotrimazole
SMILESClC1=CC=CC=C1C(N1C=CN=C1)(C1=CC=CC=C1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H
InChI KeyVNFPBHJOKIVQEB-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue Locations
  • Skin
Applications
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point154-156°C
Boiling PointNot Available
Solubility29.84 mg/mL
Predicted Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP5.48ALOGPS
logP5.84ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)6.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.82 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.76 m³·mol⁻¹ChemAxon
Polarizability36.25 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0059-6090000000-3cccc4c11a7c5a63573dNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-9ac001e37a55e61bc916Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0290000000-6285150b307e50af52c7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016u-0690000000-5814802384fae84ca3dfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-23b69c41217f6b148307Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016r-0960000000-5b3632c056ca1c0fa601Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016r-0950000000-bcb189995c8cdcd62304Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-f1d5f44ac74388f9bf4fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-1490000000-1ed188e9911ad62a7fc7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0390000000-c2f0490842646cf25d56Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014l-3970000000-0cf80068015e539b67c9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00or-0391000000-e8d9d4c77703a87fdcd8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-0df2bee4ed15192bc0b6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-f0198e4e7eaad2f34147Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00or-0490000000-53d8902c6f7211fc3c50Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0950000000-168bf9867190bc3708b3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0950000000-c0c372245eb2fe021e2eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-23b69c41217f6b148307Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0090000000-f1d5f44ac74388f9bf4fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016r-0960000000-5b3632c056ca1c0fa601Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00or-0391000000-e8d9d4c77703a87fdcd8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0019000000-a5e5b5c85ea879e2f63bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kb-1039000000-cf9a51f1cb5d717c4169Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-9280000000-7b57b00ebea4c6a2f864Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0009000000-416f1aa58c794269d038Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1009000000-25f48116b270c282f477Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-8192000000-fb089a74161c7e17e5daNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0009000000-f3594e47bbeca44d3ee5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0009000000-f3594e47bbeca44d3ee5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0296-2069000000-8ac1db9f2654b87eae4dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0090000000-0c9f74a3b432bc932f55Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0090000000-0c9f74a3b432bc932f55Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0090000000-dd86819eae3e6772c834Not AvailableView Spectrum
MSMS Spectrumsplash10-004i-1490000000-442fa75d6a2d80321e36Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityClotrimazole interacts with yeast 14-α demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the membrane. In this way, clotrimazole inhibits ergosterol synthesis, resulting in increased cellular permeability. Clotrimazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsSymptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning, and general irritation of the skin, and cramps.
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
998.0Log mg/kg[560:1800]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
115Drinking waterDrinking water & water supplyNot Available
233BrushesPersonal care & cosmeticsNot Available
241Stomatological preparationsHealthcare, pharmaceuticals & veterinary productsNot Available
299Antifungals for dermatological useHealthcare, pharmaceuticals & veterinary productsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
490Personal care & cosmeticsNot Available
497FloorsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)91.6285
Aromatase structureClick to view 3D structureAromataseP11511HumansPredicted (SEA)7.55137
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)70.8428
Click to view 3D structureThromboxane-A synthaseP24557HumansPredicted (SEA)1.16774
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)57.9977
Lanosterol 14-alpha demethylase structureClick to view 3D structureLanosterol 14-alpha demethylaseQ16850HumansPredicted (SEA)0.700643
Steroid 17-alpha-hydroxylase/17,20 lyase structureClick to view 3D structureSteroid 17-alpha-hydroxylase/17,20 lyaseP05093HumansPredicted (SEA)6.77288
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)176.796
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)144.099
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)172.358
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)100.815
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)37.3676
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)83.9215
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)57.0635
Muscarinic acetylcholine receptor M1 structureClick to view 3D structureMuscarinic acetylcholine receptor M1P11229HumansPredicted (SEA)34.6429
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)68.663
Sodium-dependent dopamine transporter structureClick to view 3D structureSodium-dependent dopamine transporterQ01959HumansPredicted (SEA)56.4407
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)52.3147
Muscarinic acetylcholine receptor M3 structureClick to view 3D structureMuscarinic acetylcholine receptor M3P20309HumansPredicted (SEA)23.9776
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)82.9873
Substance-K receptor structureClick to view 3D structureSubstance-K receptorP21452HumansPredicted (SEA)41.1822
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)128.918
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)22.187
D(1A) dopamine receptor structureClick to view 3D structureD(1A) dopamine receptorP21728HumansPredicted (SEA)75.0467
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP41143HumansPredicted (SEA)211.205
Nuclear receptor subfamily 1 group I member 2 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 2O75469HumansKnownNot Available
Bile acid receptor structureClick to view 3D structureBile acid receptorQ96RI1HumansKnownNot Available
Intermediate conductance calcium-activated potassium channel protein 4 structureClick to view 3D structureIntermediate conductance calcium-activated potassium channel protein 4O15554HumansKnownClotrimazole interacts with yeast 14-α demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the membrane. In this way, clotrimazole inhibits ergosterol synthesis, resulting in increased cellular permeability. Clotrimazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel.
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansKnownNot Available
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P08183HumansKnownNot Available
C-X-C chemokine receptor type 1 structureClick to view 3D structureC-X-C chemokine receptor type 1P25024HumansKnownNot Available
Aromatase structureClick to view 3D structureAromataseP11511HumansKnownNot Available
Lanosterol 14-alpha demethylase structureClick to view 3D structureLanosterol 14-alpha demethylaseQ16850HumansKnownNot Available
Malate dehydrogenase, cytoplasmic structureClick to view 3D structureMalate dehydrogenase, cytoplasmicP40925HumansKnownNot Available
Nuclear receptor subfamily 1 group I member 3 structureClick to view 3D structureNuclear receptor subfamily 1 group I member 3Q14994HumansKnownNot Available
Potassium voltage-gated channel subfamily A member 3 structureClick to view 3D structurePotassium voltage-gated channel subfamily A member 3P22001HumansKnownNot Available
Steroid 17-alpha-hydroxylase/17,20 lyase structureClick to view 3D structureSteroid 17-alpha-hydroxylase/17,20 lyaseP05093HumansKnownNot Available
Vasopressin V2 receptor structureClick to view 3D structureVasopressin V2 receptorP30518HumansKnownNot Available
Hypoxia-inducible factor 1-alpha structureClick to view 3D structureHypoxia-inducible factor 1-alphaQ16665HumansKnownNot Available
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansKnownNot Available
Estrogen receptor structureClick to view 3D structureEstrogen receptorP03372HumansKnownNot Available
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansKnownNot Available
Aryl hydrocarbon receptor structureClick to view 3D structureAryl hydrocarbon receptorP35869HumansKnownNot Available
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansKnownNot Available
Concentrations
Not Available
External Links
IdentifiersNot Available
References
Synthesis Reference

Buechel, K.H., et al; South African Patent 69/0039; January 3, 1969; assigned to Farben- Buechel, K.H., Regel, E. and Plempel, M.; US. Patent 3,660,577; May 2,1972; and U.S. fabriken Bayer AG, Germany.
Patent 3,705,172; Dec. 5,1972; both assigned to Farbenfabriken Bayer A.G. (Germany).

MSDSLink
General ReferencesNot Available