<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">4789</id>
  <title>T3D4734</title>
  <common-name>Salmeterol</common-name>
  <description>Salmeterol is a long-acting beta2-adrenergic receptor agonist drug that is currently prescribed for the treatment of asthma and chronic obstructive pulmonary disease COPD.</description>
  <cas>89365-50-4</cas>
  <pubchem-id>5152</pubchem-id>
  <chemical-formula>C25H37NO4</chemical-formula>
  <weight nil="true"/>
  <appearance>White powder.</appearance>
  <melting-point>75.5-76.5°C</melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>Sparingly soluble</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Because of the small therapeutic dose, systemic levels of salmeterol are low or undetectable after inhalation of recommended doses.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Salmeterol's long, lipophilic side chain binds to exosites near beta(2)-receptors in the lungs and on bronchiolar smooth muscle, allowing the active portion of the molecule to remain at the receptor site, continually binding and releasing. Beta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.</mechanism-of-toxicity>
  <metabolism>Hepatic, metabolized by hydroxylation via CYP3A4Half Life: 5.5 hours</metabolism>
  <toxicity>By the oral route, no deaths occurred in rats at 1,000 mg/kg (approximately 81,000 times the maximum recommended daily inhalation dose in adults and approximately 38,000 times the maximum recommended daily inhalation dose in children on a mg/m&lt;sup&gt;2&lt;/sup&gt; basis).</toxicity>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>For the treatment of asthma and chronic obstructive pulmonary disease (COPD).</use-source>
  <min-risk-level nil="true"/>
  <health-effects nil="true"/>
  <symptoms>Symptoms of overdose include angina (chest pain), dizziness, dry mouth, fatigue, flu-like symptoms, headache, heart irregularities, high or low blood pressure, high blood sugar, insomnia, muscle cramps, nausea, nervousness, rapid heartbeat, seizures, and tremor.</symptoms>
  <treatment nil="true"/>
  <created-at type="dateTime">2014-09-11T05:13:58Z</created-at>
  <updated-at type="dateTime">2026-03-31T19:02:27Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Salmeterol</wikipedia>
  <uniprot-id nil="true"/>
  <kegg-compound-id>C07241</kegg-compound-id>
  <omim-id nil="true"/>
  <chebi-id nil="true"/>
  <biocyc-id nil="true"/>
  <ctd-id nil="true"/>
  <stitch-id nil="true"/>
  <drugbank-id>DB00938</drugbank-id>
  <pdb-id nil="true"/>
  <actor-id nil="true"/>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins nil="true"/>
  <moldb-smiles>OCC1=C(O)C=CC(=C1)C(O)CNCCCCCCOCCCCC1=CC=CC=C1</moldb-smiles>
  <moldb-formula>C25H37NO4</moldb-formula>
  <moldb-inchi>InChI=1S/C25H37NO4/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2</moldb-inchi>
  <moldb-inchikey>GIIZNNXWQWCKIB-UHFFFAOYSA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">415.5656</moldb-average-mass>
  <moldb-mono-mass type="decimal">415.272258677</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>4.2</logp>
  <hmdb-id nil="true"/>
  <chembl-id>CHEMBL1263</chembl-id>
  <chemspider-id>4968</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;Panayiotis Procopiou, &amp;#8220;Novel process for preparing salmeterol.&amp;#8221; U.S. Patent US20030162840, issued August 28, 2003.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM003691</chemdb-id>
  <dsstox-id>DTXSID6023571</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00010340</susdat-id>
  <iupac>4-(1-hydroxy-2-{[6-(4-phenylbutoxy)hexyl]amino}ethyl)-2-(hydroxymethyl)phenol</iupac>
</compound>
