Record Information
Version1.0
Creation date2011-09-21 00:31:53 UTC
Update date2015-10-09 22:32:33 UTC
Primary IDFDB023578
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTolnaftate
DescriptionTolnaftate is a synthetic over-the-counter anti-fungal agent. It may come as a cream, powder, spray, or liquid aerosol, and is used to treat jock itch, athlete's foot and ringworm. It is sold under several brand names, most notably Tinactin (Schering-Plough Corporation) and Odor-Eaters (Combe Incorporated). Other brands are Absorbine, Aftate, Desenex, Genaspor, NP 27, and Ting.and Odor-Eaters (Combe Incorporated). Other brands are Absorbine, Aftate, Desenex, Genaspor, NP 27, and Ting. [HMDB]
CAS Number2398-96-1
Structure
Thumb
Synonyms
SynonymSource
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
Aftate for Athlete's Foot Gelhmdb
Aftate for Jock Itch Aerosol Spray Powderhmdb
Aftate for Jock Itch Gelhmdb
Aftate for Jock Itch Sprinkle Powderhmdb
Dr. Scholl's Athlete's Foot Sprayhmdb
Genaspore Creamhmdb
Hi-Alarzinhmdb
NP-27 Spray Powderhmdb
Pitrex Creamhmdb
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
Ting Antifungal Creamhmdb
Ting Antifungal Powderhmdb
Ting Antifungal Spray Liquidhmdb
Ting Antifungal Spray Powderhmdb
Ting Productshmdb
Tolnaftatehmdb
Zeasorb-AFhmdb
Zeasorb-AF Powderhmdb
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
Chemical FormulaC19H17NOS
IUPAC nameN-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide
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
Isomeric SMILESCN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C1
Average Molecular Weight307.409
Monoisotopic Molecular Weight307.103084861
Classification
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
Ontology
Disposition

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTolnaftate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00xr-0900000000-79ecbdc568d82d58099cSpectrum
Predicted GC-MSTolnaftate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-052b-0905000000-19e117da217d372632e22012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kb-0900000000-a065921efa544c82d9722012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9600000000-19faf0e6dcd285dad8d12012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-c4dd1b126170bea2c6202017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-0002-0900000000-b026e71179265a982a402017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-0900000000-a17707ff263e82d6e00e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00di-3900000000-d0563822804c2844660b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-006x-9700000000-a217b6444068e14062352017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-00kf-9200000000-dc89d8219d5ce2567f3c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-01ot-0901000000-c6fc83b073e80d5851f52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0900000000-b026e71179265a982a402021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0002-0900000000-c4dd1b126170bea2c6202021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-00kf-9200000000-dc89d8219d5ce2567f3c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-006x-9700000000-a217b6444068e14062352021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0a4j-0908000000-5202387eefde386bfb1a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0002-0900000000-02d86c1363cdce6a12542021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Positivesplash10-0a4j-0908000000-2d24973a40475e59d8cd2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Positivesplash10-006t-0900000000-cc4b44219e6a91aa19ef2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-00di-1900000000-b191679e9b4cb68f451f2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-12106483104ee4c1de122017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0209000000-29d902e78a1508311fbd2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fxx-8920000000-3cdabd44b6311142285d2017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-007340f99a6e585a149c2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0309000000-2d03a82089f2eff29cff2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000f-3921000000-f20e5c4ad5cecb13df862017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
ChemSpider ID5309
ChEMBL IDCHEMBL83668
KEGG Compound IDNot Available
Pubchem Compound ID5510
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB00525
HMDB IDHMDB05005
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDTolnaftate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference