<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:31:53 UTC</creation_date>
  <update_date>2015-10-09 22:32:33 UTC</update_date>
  <accession>FDB023578</accession>
  <name>Tolnaftate</name>
  <description>Tolnaftate 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]</description>
  <synonyms>
    <synonym>2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamate</synonym>
    <synonym>2-Naphthyl N-methyl-N-(3-tolyl)thionocarbamic acid</synonym>
    <synonym>Aftate</synonym>
    <synonym>Aftate for Athlete's Foot Gel</synonym>
    <synonym>Aftate for Jock Itch Aerosol Spray Powder</synonym>
    <synonym>Aftate for Jock Itch Gel</synonym>
    <synonym>Aftate for Jock Itch Sprinkle Powder</synonym>
    <synonym>Chinofungin</synonym>
    <synonym>Dermoxin</synonym>
    <synonym>Dr. Scholl's Athlete's Foot Spray</synonym>
    <synonym>Dungistop</synonym>
    <synonym>Focusan</synonym>
    <synonym>Fungistop</synonym>
    <synonym>Genaspore Cream</synonym>
    <synonym>Hi-Alarzin</synonym>
    <synonym>Hi-alazin</synonym>
    <synonym>m,N-Dimethylthiocarbanilate O-2-naphthyl ester</synonym>
    <synonym>m,N-Dimethylthiocarbanilic acid O-2-naphthyl ester</synonym>
    <synonym>Methyl (3-methylphenyl)carbamothioate O-2-naphthalenyl ester</synonym>
    <synonym>Methyl (3-methylphenyl)carbamothioic acid O-2-naphthalenyl ester</synonym>
    <synonym>N-Methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide</synonym>
    <synonym>Naphthiomate T</synonym>
    <synonym>Naphthiomate-T</synonym>
    <synonym>NP-27 Cream</synonym>
    <synonym>NP-27 Powder</synonym>
    <synonym>NP-27 Solution</synonym>
    <synonym>NP-27 Spray Powder</synonym>
    <synonym>O-2-Naphthyl m,N-dimethylthiocarbanilate</synonym>
    <synonym>O-2-Naphthyl m,N-dimethylthiocarbanilic acid</synonym>
    <synonym>Phytoderm</synonym>
    <synonym>Pitrex</synonym>
    <synonym>Pitrex Cream</synonym>
    <synonym>Prestwick_472</synonym>
    <synonym>Separin</synonym>
    <synonym>Sorgoa</synonym>
    <synonym>Sporiline</synonym>
    <synonym>Timoped</synonym>
    <synonym>Tinactin</synonym>
    <synonym>Tinactin Aerosol Liquid</synonym>
    <synonym>Tinactin Aerosol Powder</synonym>
    <synonym>Tinactin Antifungal Deodorant Powder Aerosol</synonym>
    <synonym>Tinactin Cream</synonym>
    <synonym>Tinactin Jock Itch Aerosol Powder</synonym>
    <synonym>Tinactin Jock Itch Cream</synonym>
    <synonym>Tinactin Jock Itch Spray Powder</synonym>
    <synonym>Tinactin Plus Aerosol Powder</synonym>
    <synonym>Tinactin Plus Powder</synonym>
    <synonym>Tinactin Powder</synonym>
    <synonym>Tinactin Solution</synonym>
    <synonym>Tinaderm</synonym>
    <synonym>Tinavet</synonym>
    <synonym>Ting Antifungal Cream</synonym>
    <synonym>Ting Antifungal Powder</synonym>
    <synonym>Ting Antifungal Spray Liquid</synonym>
    <synonym>Ting Antifungal Spray Powder</synonym>
    <synonym>Ting Products</synonym>
    <synonym>Tniaderm</synonym>
    <synonym>Tolnaftate</synonym>
    <synonym>Tolnaftato</synonym>
    <synonym>Tolnaftatum</synonym>
    <synonym>Tolnaftic acid</synonym>
    <synonym>Tolnaphthate</synonym>
    <synonym>Tolnaphthic acid</synonym>
    <synonym>Tolsanil</synonym>
    <synonym>Tonoftal</synonym>
    <synonym>Tritin</synonym>
    <synonym>Zeasorb-AF</synonym>
    <synonym>Zeasorb-AF Powder</synonym>
  </synonyms>
  <chemical_formula>C19H17NOS</chemical_formula>
  <average_molecular_weight>307.409</average_molecular_weight>
  <monisotopic_moleculate_weight>307.103084861</monisotopic_moleculate_weight>
  <iupac_name>N-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide</iupac_name>
  <traditional_iupac>tolnaftate</traditional_iupac>
  <cas_registry_number>2398-96-1</cas_registry_number>
  <smiles>CN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C1</smiles>
  <inchi>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>
  <inchikey>FUSNMLFNXJSCDI-UHFFFAOYSA-N</inchikey>
  <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.</description>
    <direct_parent>Naphthalenes</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Benzenoids</super_class>
    <class>Naphthalenes</class>
    <sub_class/>
    <molecular_framework>Aromatic homopolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organonitrogen compounds</alternative_parent>
      <alternative_parent>Organooxygen compounds</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Thiocarbamic acid esters</alternative_parent>
      <alternative_parent>Toluenes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homopolycyclic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Naphthalene</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Thiocarbamic acid derivative</substituent>
      <substituent>Thiocarbamic acid ester</substituent>
      <substituent>Toluene</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>monothiocarbamic ester</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>4.87</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.75</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>5.46e-04 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>5.75</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>0.075</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>N-methyl-N-(3-methylphenyl)-1-(naphthalen-2-yloxy)methanethioamide</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>307.409</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>307.103084861</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CN(C(=S)OC1=CC2=CC=CC=C2C=C1)C1=CC=CC(C)=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C19H17NOS</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>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</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>FUSNMLFNXJSCDI-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>12.47</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>94.92</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>34.22</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>6158</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>171407</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>2016</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrTwoD</type>
      <spectrum_id>1951</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2436</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2437</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2438</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>245769</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>245770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>245771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>265713</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>265714</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>265715</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443770</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443771</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443772</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443773</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443774</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>443775</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>450813</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2231650</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2232563</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2234035</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2234920</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2237571</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2244192</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2245886</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2246380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2247923</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB05005</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id/>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
