<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">2999</id>
  <title>T3D2957</title>
  <common-name>Balsalazide</common-name>
  <description>Balsalazide is an anti-inflammatory drug used in the treatment of Inflammatory Bowel Disease. It is sold under the name "Colazal" in the US and "Colazide" in the UK.The chemical name is (E)-5-[[-4-(2-carboxyethyl) aminocarbonyl] phenyl]azo] -2-hydroxybenzoic acid. It is usually administered as the disodium salt.Balsalazide releases mesalazine, also known as 5-aminosalicylic acid, or 5-ASA, in the large intestine. Its advantage over that drug in the treatment of Ulcerative colitis is believed to be the delivery of the active agent past the small intestine to the large intestine, the active site of ulcerative colitis.</description>
  <cas>80573-04-2</cas>
  <pubchem-id>6335412</pubchem-id>
  <chemical-formula>C17H15N3O6</chemical-formula>
  <weight>357.096090</weight>
  <appearance>White powder.</appearance>
  <melting-point></melting-point>
  <boiling-point nil="true"/>
  <density nil="true"/>
  <solubility>Freely soluble as disodium salt</solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral. Low and variable, intact balsalazide is poorly absorbed systemically.</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>The mechanism of action of 5-aminosalicylic acid is unknown, but appears exert its anti-inflammatory effects locally (in the GI tract) rather than systemically. Mucosal production of arachidonic acid metabolites, both through the cyclooxygenase pathways (catalyzes the formation of prostaglandin precursors from arachidonic acid), and through the lipoxygenase pathways (catalyzes the formation of leukotrienes and hydroxyeicosatetraenoic acids from arachidonic acid and its metabolites), is increased in patients with chronic inflammatory bowel disease. Therefore, it is possible that 5-aminosalicylic acid diminishes inflammation by blocking production of arachidonic acid metabolites in the colon through both the inhibition of cyclooxygenase and lipoxygenase.</mechanism-of-toxicity>
  <metabolism>Cleaved in the colon via bacterial azoreduction to 5-aminosalicylic acid (5&amp;ndash;ASA) and 4-aminobenzoyl-beta-alanine, the inactive carrier moiety.Route of Elimination: The products of the azoreduction of this compound, 5-ASA and 4-aminobenzoyl-beta-alanine, and their N-acetylated metabolites have been identified in plasma, urine and feces. Following single-dose administration of 2.25 g COLAZAL (three 750 mg capsules) under fasting conditions in healthy subjects, mean urinary recovery of balsalazide, 5-ASA, and N-Ac-5-ASA was 0.20%, 0.22% and 10.2%, respectively.Half Life: Half-life could not be determined.</metabolism>
  <toxicity nil="true"/>
  <lethaldose nil="true"/>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Used in the treatment of inflammatory bowel disease. [Wikipedia]</use-source>
  <min-risk-level nil="true"/>
  <health-effects></health-effects>
  <symptoms>Symptoms include headache, abdominal pain, upset stomach, dry mouth, yellowing of the skin or eyes, bloating or swelling of the stomach, and fever, sore throat, or flu-like symptoms. (L1870)</symptoms>
  <treatment>If an overdose occurs with Balsalazide, treatment should be supportive, with particular attention to correction of electrolyte abnormalities. (L1712)</treatment>
  <created-at type="dateTime">2009-07-21T20:28:10Z</created-at>
  <updated-at type="dateTime">2026-05-14T16:55:52Z</updated-at>
  <interacting-proteins nil="true"/>
  <wikipedia>Balsalazide</wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id>267413</chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id nil="true"/>
  <stitch-id>Balsalazide</stitch-id>
  <drugbank-id>DB01014</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>OC(=O)CCNC(=O)C1=CC=C(C=C1)\N=N\C1=CC=C(O)C(=C1)C(O)=O</moldb-smiles>
  <moldb-formula>C17H15N3O6</moldb-formula>
  <moldb-inchi>InChI=1S/C17H15N3O6/c21-14-6-5-12(9-13(14)17(25)26)20-19-11-3-1-10(2-4-11)16(24)18-8-7-15(22)23/h1-6,9,21H,7-8H2,(H,18,24)(H,22,23)(H,25,26)/b20-19+</moldb-inchi>
  <moldb-inchikey>IPOKCKJONYRRHP-FMQUCBEESA-N</moldb-inchikey>
  <moldb-average-mass type="decimal">357.3175</moldb-average-mass>
  <moldb-mono-mass type="decimal">357.096085227</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Solid</state>
  <logp>1.3</logp>
  <hmdb-id>HMDB15149</hmdb-id>
  <chembl-id>CHEMBL102265</chembl-id>
  <chemspider-id>10662422</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;Eckardt C. G. Wolf, Nageib Mohamed, Bhaskar Reddy Guntoori, &amp;#8220;Safe process for the preparation of balsalazide.&amp;#8221; U.S. Patent US07271253, issued September 18, 2007.&lt;/p&gt;</synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM002320</chemdb-id>
  <dsstox-id>DTXSID7040653</dsstox-id>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id>NS00038077</susdat-id>
  <iupac>5-[(1E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]-2-hydroxybenzoic acid</iupac>
  <moldb-polar-surface-area>148.65</moldb-polar-surface-area>
  <moldb-refractivity>94.37320000000001</moldb-refractivity>
  <moldb-polarizability>35.98486676626132</moldb-polarizability>
  <moldb-rotatable-bond-count>7</moldb-rotatable-bond-count>
  <moldb-acceptor-count>8</moldb-acceptor-count>
  <moldb-donor-count>4</moldb-donor-count>
  <moldb-pka-strongest-acidic>3.0649272543262662</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-0.03339614995957785</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-2</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>3.37</moldb-alogps-logp>
  <moldb-alogps-logs>-3.76</moldb-alogps-logs>
  <moldb-alogps-solubility>6.21e-02 g/l</moldb-alogps-solubility>
</compound>
