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<compound>
  <id type="integer">2996</id>
  <title>T3D2954</title>
  <common-name>Frovatriptan</common-name>
  <description>Frovatriptan is an exogenous organic compound with the formula C14H17N3O and an average molecular weight of 243.30 g/mol. It exists as a solid at room temperature. Frovatriptan belongs to the carbazoles, a subclass of indoles and derivatives within the organic compounds. This compound is recorded as being found in or released from five sources, including analgesics within healthcare, pharmaceuticals and veterinary products, household cleaning and consumer products such as other smoking requisites and non electric simulated smoking devices, and electrical and electronic equipment including television systems and electric hearing aids. The recorded exposure route is oral.

Frovatriptan targets the 5-hydroxytryptamine receptor 1B (HTR1B) and 5-hydroxytryptamine receptor 1D (HTR1D). Three distinct pharmacological actions are implicated in the antimigraine effect of triptans: the stimulation of presynaptic 5-HT1D receptors, which inhibits dural inflammation and vasodilation; direct inhibition of trigeminal nuclei cell excitability through 5-HT1B/1D receptor agonism in the brainstem; and vasoconstriction of pial, cerebral, dural, or meningeal vessels resulting from vascular 5-HT1B receptor agonism.</description>
  <cas>158747-02-5</cas>
  <pubchem-id>77992</pubchem-id>
  <chemical-formula>C14H17N3O</chemical-formula>
  <weight>243.137160</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>Soluble</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Frovatriptan is rapidly absorbed from the duodenum, but has low oral bioavailability.</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-HT&lt;sub&gt;1D&lt;/sub&gt; receptors, which serves to inhibit both dural vasodilation and inflammation; (2) direct inhibition of trigeminal nuclei cell excitability via 5-HT&lt;sub&gt;1B/1D&lt;/sub&gt; receptor agonism in the brainstem and (3) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT&lt;sub&gt;1B&lt;/sub&gt; receptor agonism.</mechanism-of-toxicity>
  <metabolism>In vitro, cytochrome P450 1A2 appears to be the principal enzyme involved in the metabolism of frovatriptan to several metabolites including hydroxylated frovatriptan, N-acetyl desmethyl frovatriptan, hydroxylated N-acetyl desmethyl frovatriptan and desmethyl frovatriptan, and several other minor metabolites. Desmethyl frovatriptan has lower affinity for 5-HT&lt;sub&gt;1B/1D&lt;/sub&gt; receptors compared to the parent compound. The N-acetyl desmethyl metabolite has no significant affinity for 5-HT receptors. The activity of the other metabolites is unknown.Route of Elimination: Radiolabeled compounds excreted in urine were unchanged frovatriptan, hydroxylated frovatriptan, N-acetyl desmethyl frovatriptan, hydroxylated N-acetyl desmethyl frovatriptan and desmethyl frovatriptan, together with several other minor metabolites. Less than 10% of frovatriptan was excreted in urine after an oral dose.Half Life: 26 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>There is no direct experience of any patient taking an overdose of Frovatriptan. The maximum single dose of frovatriptan given to male and female patients with migraine was 40 mg (16 times the clinical dose) and the maximum single dose given to healthy male subjects was 100 mg (40 times the clinical dose) without significant adverse events.</symptoms>
  <treatment>As with other 5-HT1 receptor agonists, there is no specific antidote for frovatriptan. The elimination half-life of frovatriptan is 26 hours, therefore if overdose occurs, the patient should be monitored closely for at least 48 hours and be given any necessary symptomatic treatment. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:28:08Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:55:21Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Frovatriptan</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>350328</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Frovatriptan</stitch-id>
  <drugbank-id>DB00998</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>CN[C@@H]1CCC2=C(C1)C1=C(N2)C=CC(=C1)C(N)=O</moldb-smiles>
  <moldb-formula>C14H17N3O</moldb-formula>
  <moldb-inchi>InChI=1S/C14H17N3O/c1-16-9-3-5-13-11(7-9)10-6-8(14(15)18)2-4-12(10)17-13/h2,4,6,9,16-17H,3,5,7H2,1H3,(H2,15,18)/t9-/m1/s1</moldb-inchi>
  <moldb-inchikey>XPSQPHWEGNHMSK-SECBINFHSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">243.3043</moldb-average-mass>
  <moldb-mono-mass type="decimal">243.137162181</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>0.9</logp>
  <hmdb-id>HMDB15133</hmdb-id>
  <chembl-id>CHEMBL1279</chembl-id>
  <chemspider-id>70378</chemspider-id>
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  <biodb-id nil="true"/>
  <synthesis-reference>&lt;p&gt;Samir Naik, Anthony Crasto, Narendra Joshi, Sachin Srivastava, &amp;#8220;Amorphous frovatriptan succinate and process for the preparation thereof.&amp;#8221; U.S. Patent US20070299123, issued December 27, 2007.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002317</chemdb-id>
  <dsstox-id>DTXSID0023080</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00007851</susdat-id>
  <iupac>(3R)-3-(methylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamide</iupac>
  <moldb-polar-surface-area>70.91</moldb-polar-surface-area>
  <moldb-refractivity>71.8382</moldb-refractivity>
  <moldb-polarizability>27.552154348371012</moldb-polarizability>
  <moldb-rotatable-bond-count>2</moldb-rotatable-bond-count>
  <moldb-acceptor-count>2</moldb-acceptor-count>
  <moldb-donor-count>3</moldb-donor-count>
  <moldb-pka-strongest-acidic>14.5361936626193</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>10.421212164263157</moldb-pka-strongest-basic>
  <moldb-physiological-charge>1</moldb-physiological-charge>
  <moldb-number-of-rings>3</moldb-number-of-rings>
  <moldb-alogps-logp>1.20</moldb-alogps-logp>
  <moldb-alogps-logs>-3.30</moldb-alogps-logs>
  <moldb-alogps-solubility>1.23e-01 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organoheterocyclic compounds</superklass>
  <klass>Indoles and derivatives</klass>
  <subklass>Carbazoles</subklass>
  <paper-count type="integer">248</paper-count>
  <sync-id>CED0010031</sync-id>
  <structure-inchikey>XPSQPHWEGNHMSK-SECBINFHSA-N</structure-inchikey>
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  <structure-indexed-at type="dateTime">2026-09-19T04:00:40Z</structure-indexed-at>
</compound>
