Tolnaftate (CED0011200)

Record Information
Version1.0
Creation Date2016-05-22 04:40:34 UTC
Update Date2026-05-14 16:41:12 UTC
Accession NumberCHEM017820
Identification
Common NameTolnaftate
ClassSmall Molecule
Description
Tolnaftate is an organic compound with the chemical formula C19H17NOS and an average molecular weight of 307.41 g/mol. Tolnaftate belongs to the naphthalenes, a class of benzenoids within the organic compounds. This compound serves as an industrial biocide. It is found in or released from three recorded sources, including amplifiers and antennas within electrical and electronic equipment, as well as antifungals for dermatological use within healthcare, pharmaceuticals, and veterinary products. The recorded route of exposure for this substance is topical. Regarding its biochemical activity, there are two recorded protein targets for tolnaftate: it acts as an inhibitor of Squalene epoxidase ERG1 and Squalene monooxygenase (SQLE).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamateChEBI
m,N-Dimethylthiocarbanilic acid O-2-naphthyl esterChEBI
Methyl (3-methylphenyl)carbamothioic acid O-2-naphthalenyl esterChEBI
N-Methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamideChEBI
O-2-Naphthyl m,N-dimethylthiocarbanilateChEBI
SeparinChEBI
TinactinChEBI
TolnaftatoChEBI
TolnaftatumChEBI
TolnaphthateChEBI
2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamic acidGenerator
m,N-Dimethylthiocarbanilate O-2-naphthyl esterGenerator
Methyl (3-methylphenyl)carbamothioate O-2-naphthalenyl esterGenerator
O-2-Naphthyl m,N-dimethylthiocarbanilic acidGenerator
Tolnaphthic acidGenerator
Tolnaftic acidGenerator
AftateHMDB, MeSH
Aftate for athlete's foot gelHMDB
Aftate for jock itch aerosol spray powderHMDB
Aftate for jock itch gelHMDB
Aftate for jock itch sprinkle powderHMDB
ChinofunginHMDB, MeSH
DermoxinHMDB
Dr. scholl's athlete's foot sprayHMDB
DungistopHMDB
FocusanHMDB
FungistopHMDB
Genaspore creamHMDB
Hi-alarzinHMDB
Hi-alazinHMDB
Naphthiomate THMDB
Naphthiomate-THMDB
NP-27 CreamHMDB
NP-27 PowderHMDB
NP-27 SolutionHMDB
NP-27 Spray powderHMDB
PhytodermHMDB
PitrexHMDB
Pitrex creamHMDB
Prestwick_472HMDB
SorgoaHMDB
SporilineHMDB, MeSH
TimopedHMDB
Tinactin aerosol liquidHMDB
Tinactin aerosol powderHMDB
Tinactin antifungal deodorant powder aerosolHMDB
Tinactin creamHMDB
Tinactin jock itch aerosol powderHMDB
Tinactin jock itch creamHMDB
Tinactin jock itch spray powderHMDB
Tinactin plus aerosol powderHMDB
Tinactin plus powderHMDB
Tinactin powderHMDB
Tinactin solutionHMDB
TinadermHMDB, MeSH
TinavetHMDB
Ting antifungal creamHMDB
Ting antifungal powderHMDB
Ting antifungal spray liquidHMDB
Ting antifungal spray powderHMDB
Ting productsHMDB
TniadermHMDB
TolsanilHMDB
TonoftalHMDB, MeSH
TritinHMDB
Zeasorb-afHMDB
Zeasorb-af powderHMDB
Chinosol brand OF tolnaftateMeSH, HMDB
GenasporMeSH, HMDB
Pedinol brand 2 OF tolnaftateMeSH, HMDB
Purder N, tolnaftatMeSH, HMDB
Tolnaftat purder NMeSH, HMDB
Wernigerode brand OF tolnaftateMeSH, HMDB
Bioglan brand OF tolnaftateMeSH, HMDB
ChloriseptMeSH, HMDB
CuratinMeSH, HMDB
Douglas brand OF tolnaftateMeSH, HMDB
Insight brand OF tolnaftateMeSH, HMDB
Isdin brand OF tolnaftateMeSH, HMDB
NP 27MeSH, HMDB
Ony-clearMeSH, HMDB
Pedinol brand 1 OF tolnaftateMeSH, HMDB
Schering-plough brand 1 OF tolnaftateMeSH, HMDB
Thompson brand OF tolnaftateMeSH, HMDB
TinatoxMeSH, HMDB
TineafaxMeSH, HMDB
Zenith brand OF tolnaftateMeSH, HMDB
BreezeeMeSH, HMDB
Essex brand OF tolnaftateMeSH, HMDB
Schering brand OF tolnaftateMeSH, HMDB
Stiefel brand OF tolnaftateMeSH, HMDB
Tolnaftate douglas brandMeSH, HMDB
ZeaSorbMeSH, HMDB
Carter wallace brand OF tolnaftateMeSH, HMDB
MicoisdinMeSH, HMDB
NP-27MeSH, HMDB
Ony clearMeSH, HMDB
Schering-plough brand 2 OF tolnaftateMeSH, HMDB
TingMeSH, HMDB
Tolnaftate schering brandMeSH, HMDB
Chemical FormulaC19H17NOS
Average Molecular Mass307.409 g/mol
Monoisotopic Mass307.103 g/mol
CAS Registry Number2398-96-1
IUPAC NameN-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide
Traditional Nametolnaftate
SMILESCN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C1
InChI IdentifierInChI=1S/C19H17NOS/c1-14-6-5-9-17(12-14)20(2)19(22)21-18-11-10-15-7-3-4-8-16(15)13-18/h3-13H,1-2H3
InChI KeyFUSNMLFNXJSCDI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Toluene
  • Monocyclic benzene moiety
  • Thiocarbamic acid ester
  • Thiocarbamic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00055 g/LALOGPS
logP4.87ALOGPS
logP5.75ChemAxon
logS-5.8ALOGPS
pKa (Strongest Basic)0.075ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.47 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity94.92 m³·mol⁻¹ChemAxon
Polarizability34.22 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00xr-0900000000-79ecbdc568d82d58099cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052b-0905000000-19e117da217d372632e2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kb-0900000000-a065921efa544c82d972Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9600000000-19faf0e6dcd285dad8d1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900000000-c4dd1b126170bea2c620Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900000000-b026e71179265a982a40Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-a17707ff263e82d6e00eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-3900000000-d0563822804c2844660bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-006x-9700000000-a217b6444068e1406235Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kf-9200000000-dc89d8219d5ce2567f3cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ot-0901000000-c6fc83b073e80d5851f5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900000000-b026e71179265a982a40Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900000000-c4dd1b126170bea2c620Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kf-9200000000-dc89d8219d5ce2567f3cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-006x-9700000000-a217b6444068e1406235Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4j-0908000000-5202387eefde386bfb1aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900000000-02d86c1363cdce6a1254Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4j-0908000000-2d24973a40475e59d8cdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-006t-0900000000-cc4b44219e6a91aa19efNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-b191679e9b4cb68f451fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dl-7900000000-07c809cbb632cbfb9a84Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9300000000-d629934791b126cd7d9bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-3900000000-d0563822804c2844660bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-a17707ff263e82d6e00eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-12106483104ee4c1de12Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0209000000-29d902e78a1508311fbdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fxx-8920000000-3cdabd44b6311142285dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-007340f99a6e585a149cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0309000000-2d03a82089f2eff29cffNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000f-3921000000-f20e5c4ad5cecb13df86Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0109000000-495e2f382db8daab5a58Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000l-0901000000-4eb961250b75b2b56a5eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1910000000-b83e88dc8bf22a82a180Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0bt9-0609000000-cffe1b7b749dbeaf5e1cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0229-0900000000-53858f928e9d11b0dc7aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9500000000-07a9aaf43f0293774353Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2271.0Log mg/kg[1300:4000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
299Antifungals for dermatological useHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
609AftershavePersonal care & cosmeticsNot Available
Pathways
3 pathways
Tolnaftate Action Pathway
Tolnaftate Action Pathway
Tolnaftate Drug Metabolism Action Pathway
Tolnaftate Drug Metabolism Action Pathway
Tolnaftate Predicted Metabolism Pathway
Tolnaftate Predicted Metabolism Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)70.1422
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)87.5025
Click to view 3D structureCytochrome P450 2A5P20852Mus musculusPredicted (SEA)8.17417
Click to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP12527Rattus norvegicusPredicted (SEA)208.169
Platelet-derived growth factor receptor beta structureClick to view 3D structurePlatelet-derived growth factor receptor betaP09619HumansPredicted (SEA)2175.03
Platelet-derived growth factor receptor alpha structureClick to view 3D structurePlatelet-derived growth factor receptor alphaP16234HumansPredicted (SEA)2196.75
Sentrin-specific protease 7 structureClick to view 3D structureSentrin-specific protease 7Q9BQF6HumansPredicted (SEA)575.072
Polyunsaturated fatty acid 5-lipoxygenase structureClick to view 3D structurePolyunsaturated fatty acid 5-lipoxygenaseP09917HumansPredicted (SEA)567.287
Click to view 3D structureSecernin-3Q0VDG4HumansPredicted (SEA)13.0008
Click to view 3D structureAmine oxidase [flavin-containing] BP19643Rattus norvegicusPredicted (SEA)334.207
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)1598.24
Click to view 3D structureProtein RecAP9WHJ3Mycobacterium tuberculosisPredicted (SEA)1002.08
Click to view 3D structureCholinesteraseP81908Equus caballusPredicted (SEA)952.33
Click to view 3D structureTransient receptor potential cation channel subfamily A member 1Q6RI86Rattus norvegicusPredicted (SEA)115.762
Fibroblast growth factor receptor 1 structureClick to view 3D structureFibroblast growth factor receptor 1P11362HumansPredicted (SEA)3478.46
Cholinesterase structureClick to view 3D structureCholinesteraseP06276HumansPredicted (SEA)1115.11
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)5230.3
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)4881.77
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)2163.04
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)3008.79
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)3249.66
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)4214.45
Click to view 3D structureFatty-acid amide hydrolase 1P97612Rattus norvegicusPredicted (SEA)684.139
5-hydroxytryptamine receptor 3A structureClick to view 3D structure5-hydroxytryptamine receptor 3AP46098HumansPredicted (SEA)1063.73
Click to view 3D structureAmine oxidase [flavin-containing] AP21396Rattus norvegicusPredicted (SEA)348.142
Concentrations
Not Available
External Links
DrugBank IDDB00525
HMDB IDHMDB0005005
FooDB IDFDB023578
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTolnaftate
Chemspider ID5309
ChEBI ID9620
PubChem Compound ID5510
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=20347664
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=2061794
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20635527
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21565546
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=22125963
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24706116
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=3509341
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=4568708
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=5319027
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=5705341
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=5745067
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=5847820
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=5856396
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=5952516
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=697362
16. Ayyangar, N. R.; Wakharkar, R. D.; Deshpande, V. H.; Rai, B. An alternative method for tolnaftate. Organic Preparations and Procedures International (1990), 22(1), 128-30.