<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2981</id>
  <title>T3D2939</title>
  <common-name>Naratriptan</common-name>
  <description>Naratriptan is only found in individuals that have used or taken this drug. It is a triptan drug used for the treatment of migraine headaches. It is a selective 5-hydroxytryptamine1 receptor subtype agonist.Three distinct pharmacological actions have been implicated in the antimigraine effect of the triptans: (1) stimulation of presynaptic 5-HT1D receptors, which serves to inhibit both dural vasodilation and inflammation; (2) direct inhibition of trigeminal nuclei cell excitability via 5-HT1B/1D receptor agonism in the brainstem and (3) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT1B receptor agonism.</description>
  <cas>121679-13-8</cas>
  <pubchem-id>4440</pubchem-id>
  <chemical-formula>C17H25N3O2S</chemical-formula>
  <weight>335.166750</weight>
  <appearance>White powder.</appearance>
  <melting-point>246°C (HCl salt)</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>35 mg/mL</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Well absorbed (74% oral biovaility), absorption is rapid with peak plasma concentrations after 2-5 hours. The rate of absorption is slower during a migraine attack.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Three distinct pharmacological actions have been implicated in the antimigraine effect of the triptans: (1) stimulation of presynaptic 5-HT1D receptors, which serves to inhibit both dural vasodilation and inflammation; (2) direct inhibition of trigeminal nuclei cell excitability via 5-HT1B/1D receptor agonism in the brainstem and (3) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT1B receptor agonism.</mechanism-of-toxicity>
  <metabolism>Primarily hepatic. &lt;i&gt;In vitro,&lt;/i&gt; naratriptan is metabolized by a wide range of cytochrome P450 isoenzymes into a number of inactive metabolites.Half Life: 5-8 hours</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the acute treatment of migraine attacks with or without aura in adults.</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Symptoms of overdose include light-headedness, loss of coordination, tension in the neck, and tiredness.</symptoms>
  <treatment>There is no specific antidote to naratriptan. Standard supportive treatment should be applied as required. If the patient presents with chest pain or other symptoms consistent with angina pectoris, ECG monitoring should be performed for evidence of ischemia. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:28:01Z</created-at>
  <updated-at type="dateTime">2014-12-24T20:25:53Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Naratriptan</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id>C07792</kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>7478</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Naratriptan</stitch-id>
  <drugbank-id>DB00952</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>CNS(=O)(=O)CCC1=CC2=C(NC=C2C2CCN(C)CC2)C=C1</moldb-smiles>
  <moldb-formula>C17H25N3O2S</moldb-formula>
  <moldb-inchi>InChI=1S/C17H25N3O2S/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14/h3-4,11-12,14,18-19H,5-10H2,1-2H3</moldb-inchi>
  <moldb-inchikey>InChIKey=AMKVXSZCKVJAGH-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">335.464</moldb-average-mass>
  <moldb-mono-mass type="decimal">335.166747749</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>1.6</logp>
  <hmdb-id>HMDB15087</hmdb-id>
  <chembl-id>CHEMBL1278</chembl-id>
  <chemspider-id>4287</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Dharmaraj Ramachandra Rao, Rajendra Narayanrao Kankan, Sandip Vasant Chikhalikar, Maruti Ghagare, &amp;#8220;Process for the synthesis of naratriptan.&amp;#8221; U.S. Patent US20120220778, issued August 30, 2012.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
</compound>
