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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-10-16 12:15:48 UTC
Update Date2022-03-07 02:49:25 UTC
HMDB IDHMDB0005005
Secondary Accession Numbers
  • HMDB05005
Metabolite Identification
Common 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.
Structure
Data?1582752339
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 Weight307.409
Monoisotopic Molecular Weight307.103084861
IUPAC NameN-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide
Traditional Nametolnaftate
CAS Registry Number2398-96-1
SMILES
CN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C1
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point111 °CNot Available
Boiling Point453.38 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.12 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP5.142 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available173.639http://allccs.zhulab.cn/database/detail?ID=AllCCS00000723
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+170.77131661259
DarkChem[M-H]-172.79931661259
DeepCCS[M+H]+170.85730932474
DeepCCS[M-H]-168.49930932474
DeepCCS[M-2H]-201.38530932474
DeepCCS[M+Na]+176.9530932474
AllCCS[M+H]+171.932859911
AllCCS[M+H-H2O]+168.432859911
AllCCS[M+NH4]+175.132859911
AllCCS[M+Na]+176.032859911
AllCCS[M-H]-171.032859911
AllCCS[M+Na-2H]-169.832859911
AllCCS[M+HCOO]-168.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TolnaftateCN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C13830.8Standard polar33892256
TolnaftateCN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C12525.4Standard non polar33892256
TolnaftateCN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C12742.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tolnaftate GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xr-0900000000-79ecbdc568d82d58099c2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tolnaftate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-052b-0905000000-19e117da217d372632e22012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-00kb-0900000000-a065921efa544c82d9722012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0006-9600000000-19faf0e6dcd285dad8d12012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate LC-ESI-QFT , positive-QTOFsplash10-0002-0900000000-c4dd1b126170bea2c6202017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate LC-ESI-QFT , positive-QTOFsplash10-0002-0900000000-b026e71179265a982a402017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate LC-ESI-QFT , positive-QTOFsplash10-00di-0900000000-a17707ff263e82d6e00e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate LC-ESI-QFT , positive-QTOFsplash10-00di-3900000000-d0563822804c2844660b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate LC-ESI-QFT , positive-QTOFsplash10-006x-9700000000-a217b6444068e14062352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate LC-ESI-QFT , positive-QTOFsplash10-00kf-9200000000-dc89d8219d5ce2567f3c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate , positive-QTOFsplash10-01ot-0901000000-c6fc83b073e80d5851f52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate 30V, Positive-QTOFsplash10-0002-0900000000-b026e71179265a982a402021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate 15V, Positive-QTOFsplash10-0002-0900000000-c4dd1b126170bea2c6202021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate 90V, Positive-QTOFsplash10-00kf-9200000000-dc89d8219d5ce2567f3c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate 75V, Positive-QTOFsplash10-006x-9700000000-a217b6444068e14062352021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate 15V, Positive-QTOFsplash10-0a4j-0908000000-5202387eefde386bfb1a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate 30V, Positive-QTOFsplash10-0002-0900000000-02d86c1363cdce6a12542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate 15V, Positive-QTOFsplash10-0a4j-0908000000-2d24973a40475e59d8cd2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate 45V, Positive-QTOFsplash10-006t-0900000000-cc4b44219e6a91aa19ef2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate 60V, Positive-QTOFsplash10-00di-1900000000-b191679e9b4cb68f451f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate 75V, Positive-QTOFsplash10-00dl-7900000000-07c809cbb632cbfb9a842021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate 90V, Positive-QTOFsplash10-0006-9300000000-d629934791b126cd7d9b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate 60V, Positive-QTOFsplash10-00di-3900000000-d0563822804c2844660b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tolnaftate 45V, Positive-QTOFsplash10-00di-0900000000-a17707ff263e82d6e00e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolnaftate 10V, Negative-QTOFsplash10-0a4i-0009000000-007340f99a6e585a149c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tolnaftate 20V, Negative-QTOFsplash10-0a4i-0309000000-2d03a82089f2eff29cff2017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00525
Phenol Explorer Compound IDNot Available
FooDB IDFDB023578
KNApSAcK IDNot Available
Chemspider ID5309
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTolnaftate
METLIN IDNot Available
PubChem Compound5510
PDB IDNot Available
ChEBI ID9620
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1539591
References
Synthesis ReferenceAyyangar, 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.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available