Tolnaftate (CHEM017820)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:40:34 UTC
Update Date2016-11-09 01:15:40 UTC
Accession NumberCHEM017820
Identification
Common NameTolnaftate
ClassSmall Molecule
DescriptionA monothiocarbamic ester that is the methyl(3-tolyl)carbamothioate ester of 2-naphthol. A synthetic anti-fungal agent used to treat jock itch, athlete's foot and ringworm.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-0900000000-79ecbdc568d82d58099cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-052b-0905000000-19e117da217d372632e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kb-0900000000-a065921efa544c82d972Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9600000000-19faf0e6dcd285dad8d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-c4dd1b126170bea2c620Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-b026e71179265a982a40Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-a17707ff263e82d6e00eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-3900000000-d0563822804c2844660bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006x-9700000000-a217b6444068e1406235Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00kf-9200000000-dc89d8219d5ce2567f3cSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01ot-0901000000-c6fc83b073e80d5851f5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0900000000-b026e71179265a982a40Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0002-0900000000-c4dd1b126170bea2c620Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-00kf-9200000000-dc89d8219d5ce2567f3cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-006x-9700000000-a217b6444068e1406235Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0a4j-0908000000-5202387eefde386bfb1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0900000000-02d86c1363cdce6a1254Spectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0a4j-0908000000-2d24973a40475e59d8cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-006t-0900000000-cc4b44219e6a91aa19efSpectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-00di-1900000000-b191679e9b4cb68f451fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-12106483104ee4c1de12Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0209000000-29d902e78a1508311fbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fxx-8920000000-3cdabd44b6311142285dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-007340f99a6e585a149cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0309000000-2d03a82089f2eff29cffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-3921000000-f20e5c4ad5cecb13df86Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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.