<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2011-09-21 00:32:17 UTC</creation_date>
  <update_date>2015-07-21 06:57:47 UTC</update_date>
  <accession>FDB023604</accession>
  <name>Sumatriptan</name>
  <description>Oftentimes, serotonin levels in the brain become extremely erratic before the onset of a migraine. In an attempt to stabilize this, sumatriptan is administered to help aid in leveling the serotonin levels in the brain. Sumatriptan is structurally similar to serotonin, and is a 5-HT (5-HT1D) agonist, which is one of the receptors that serotonin binds to. The specific receptor subtype it activates is present in the cranial and basilar arteries. Activation of these receptors causes vasoconstriction of those dilated arteries. Sumatriptan is also shown to decrease the activity of the trigeminal nerve.; Sumatriptan is a triptan drug including a sulfonamide group structurally similar to serotonin, and is a 5-HT (5-HT1D) agonist, which is one of the receptors that serotonin binds to. 
Oftentimes, serotonin levels in the brain become extremely erratic before the onset of a migraine. In an attempt to stabilize this, sumatriptan is administered to help aid in leveling the serotonin levels in the brain.; A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of migraines.; Sumatriptan (Imitrex, Imigran,Imigran Recovery ) is a triptan drug including a sulfonamide group which was originally developed by Glaxo for the treatment of migraine headaches. [HMDB]</description>
  <synonyms>
    <synonym>(3-[2-(dimethylamino)Ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide</synonym>
    <synonym>(3-[2-(dimethylamino)Ethyl]-1H-indol-5-yl)-N-methylmethanesulphonamide</synonym>
    <synonym>1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide</synonym>
    <synonym>1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulphonamide</synonym>
    <synonym>3-(2-(dimethylamino)Ethyl)-N-methyl-1H-indole-5-methanesulfonamide</synonym>
    <synonym>3-(2-(dimethylamino)Ethyl)-N-methyl-1H-indole-5-methanesulphonamide</synonym>
    <synonym>3-[2-(dimethylamino)Ethyl]-N-methylindole-5-methanesulfonamide</synonym>
    <synonym>3-[2-(dimethylamino)Ethyl]-N-methylindole-5-methanesulphonamide</synonym>
    <synonym>Imigran</synonym>
    <synonym>Imigran Recovery</synonym>
    <synonym>Imitrex</synonym>
    <synonym>Sumatran</synonym>
    <synonym>Sumatriptan</synonym>
    <synonym>Sumatriptanum</synonym>
    <synonym>Sumax</synonym>
  </synonyms>
  <chemical_formula>C14H21N3O2S</chemical_formula>
  <average_molecular_weight>295.4</average_molecular_weight>
  <monisotopic_moleculate_weight>295.135447621</monisotopic_moleculate_weight>
  <iupac_name>1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide</iupac_name>
  <traditional_iupac>sumatriptan</traditional_iupac>
  <cas_registry_number>103628-46-2</cas_registry_number>
  <smiles>CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1</smiles>
  <inchi>InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3</inchi>
  <inchikey>KQKPFRSPSRPDEB-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.</description>
    <direct_parent>Tryptamines and derivatives</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organoheterocyclic compounds</super_class>
    <class>Indoles and derivatives</class>
    <sub_class>Tryptamines and derivatives</sub_class>
    <molecular_framework>Aromatic heteropolycyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>3-alkylindoles</alternative_parent>
      <alternative_parent>Aminosulfonyl compounds</alternative_parent>
      <alternative_parent>Aralkylamines</alternative_parent>
      <alternative_parent>Azacyclic compounds</alternative_parent>
      <alternative_parent>Benzenoids</alternative_parent>
      <alternative_parent>Heteroaromatic compounds</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organic sulfonamides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Organosulfonamides</alternative_parent>
      <alternative_parent>Substituted pyrroles</alternative_parent>
      <alternative_parent>Trialkylamines</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>3-alkylindole</substituent>
      <substituent>Amine</substituent>
      <substituent>Aminosulfonyl compound</substituent>
      <substituent>Aralkylamine</substituent>
      <substituent>Aromatic heteropolycyclic compound</substituent>
      <substituent>Azacycle</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Heteroaromatic compound</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Indole</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organic sulfonic acid amide</substituent>
      <substituent>Organic sulfonic acid or derivatives</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Organosulfonic acid amide</substituent>
      <substituent>Organosulfonic acid or derivatives</substituent>
      <substituent>Organosulfur compound</substituent>
      <substituent>Pyrrole</substituent>
      <substituent>Substituted pyrrole</substituent>
      <substituent>Sulfonyl</substituent>
      <substituent>Tertiary aliphatic amine</substituent>
      <substituent>Tertiary amine</substituent>
      <substituent>Tryptamine</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>sulfonamide</external_descriptor>
      <external_descriptor>tryptamines</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Solid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>1.17</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.37</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>1.27e-01 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>0.74</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>11.24</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>9.54</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>295.4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>295.135447621</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C14H21N3O2S</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>KQKPFRSPSRPDEB-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>65.2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>82.08</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>32.31</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>417</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>152288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107388</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107389</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>107390</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174360</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174361</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>174362</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374435</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>374826</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451096</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>451526</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2233568</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2235349</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2379255</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2379256</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2379257</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2556642</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2556643</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2556644</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB05037</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>10650</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce333b9fa0&gt;</reference>
    <reference>#&lt;Reference:0x000055ce333b9de8&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
    <enzyme>
      <name>5-hydroxytryptamine receptor 1B</name>
      <uniprot_id>P28222</uniprot_id>
      <uniprot_name/>
      <gene_name>HTR1B</gene_name>
    </enzyme>
    <enzyme>
      <name>5-hydroxytryptamine receptor 1D</name>
      <uniprot_id>P28221</uniprot_id>
      <uniprot_name/>
      <gene_name>HTR1D</gene_name>
    </enzyme>
    <enzyme>
      <name>5-hydroxytryptamine receptor 1F</name>
      <uniprot_id>P30939</uniprot_id>
      <uniprot_name/>
      <gene_name>HTR1F</gene_name>
    </enzyme>
    <enzyme>
      <name>Inhibitor of nuclear factor kappa-B kinase subunit beta</name>
      <uniprot_id>O14920</uniprot_id>
      <uniprot_name/>
      <gene_name>IKBKB</gene_name>
    </enzyme>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
