Balsalazide (CHEM002320)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2009-07-21 20:28:10 UTC
Update Date2026-05-14 16:55:52 UTC
Accession NumberCHEM002320
Identification
Common NameBalsalazide
ClassSmall Molecule
DescriptionBalsalazide 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Anti-Inflammatory Agent, Non-Steroidal
  • Anti-Ulcer Agent
  • Drug
  • Ester
  • Gastrointestinal Agent
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e)-5-((4-(((2-Carboxyethyl)amino)carbonyl)phenyl)azo)-2-hydroxybenzoic acidChEBI
(e)-5-({p-[(2-carboxyethyl)carbamoyl]phenyl}azo)-2-salicylic acidChEBI
3-(2-{4-[(2-carboxyethyl)carbamoyl]phenyl}hydrazinylidene)-6-oxocyclohexa-1,4-diene-1-carboxylic acidChEBI
5-[4-(2-Carboxy-ethylcarbamoyl)-phenylazo]-2-hydroxy-benzoic acidChEBI
BalsalazidaChEBI
BalsalazidoChEBI
BalsalazidumChEBI
(e)-5-((4-(((2-Carboxyethyl)amino)carbonyl)phenyl)azo)-2-hydroxybenzoateGenerator
(e)-5-({p-[(2-carboxyethyl)carbamoyl]phenyl}azo)-2-salicylateGenerator
3-(2-{4-[(2-carboxyethyl)carbamoyl]phenyl}hydrazinylidene)-6-oxocyclohexa-1,4-diene-1-carboxylateGenerator
5-[4-(2-Carboxy-ethylcarbamoyl)-phenylazo]-2-hydroxy-benzoateGenerator
Balsalazide disodiumHMDB
Chemical FormulaC17H15N3O6
Average Molecular Mass357.318 g/mol
Monoisotopic Mass357.096 g/mol
CAS Registry Number80573-04-2
IUPAC Name5-[(1E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]-2-hydroxybenzoic acid
Traditional Namebalsalazide
SMILESOC(=O)CCNC(=O)C1=CC=C(C=C1)\N=N\C1=CC=C(O)C(=C1)C(O)=O
InChI IdentifierInChI=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+
InChI KeyIPOKCKJONYRRHP-FMQUCBEESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzobenzenes
Sub ClassNot Available
Direct ParentAzobenzenes
Alternative Parents
Substituents
  • Azobenzene
  • Beta amino acid or derivatives
  • Hydroxybenzoic acid
  • Salicylic acid or derivatives
  • Salicylic acid
  • Benzoic acid
  • Benzoic acid or derivatives
  • Benzamide
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Azo compound
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityFreely soluble as disodium salt
Predicted Properties
PropertyValueSource
Water Solubility0.062 g/LALOGPS
logP3.37ALOGPS
logP3.17ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.06ChemAxon
pKa (Strongest Basic)-0.033ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area148.65 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity94.37 m³·mol⁻¹ChemAxon
Polarizability35.98 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ldi-1393000000-af92622c6ce32e802a99Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-052f-2239460000-dd6d65f067d80197bd6eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05mo-1359000000-5ac19318b9222056db99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01b9-4194000000-a389ca20ea5f71b14f1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00or-9460000000-058a3d277554ae6ad3a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0r00-0859000000-0815df00a696a3bf2ef9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0cdl-1596000000-f30b936242fc2a51a3bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-1920000000-ab19fc8210a3b9bf159aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-938e67d0a29d75e91560Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0297-0094000000-71c0a9165a9dbb26d8edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvi-0590000000-6f84da2d9032ab43467dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0019000000-5cde35cdf9191a2d0721Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-0092000000-e9ef5ce26a4f3979c212Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-2290000000-1ff988f1dc562e4db92fSpectrum
Toxicity Profile
Route of ExposureOral. Low and variable, intact balsalazide is poorly absorbed systemically.
Mechanism of ToxicityThe 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.
MetabolismCleaved in the colon via bacterial azoreduction to 5-aminosalicylic acid (5–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.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed in the treatment of inflammatory bowel disease. [Wikipedia]
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms 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. (5)
TreatmentIf an overdose occurs with Balsalazide, treatment should be supportive, with particular attention to correction of electrolyte abnormalities. (4)
Concentrations
Not Available
DrugBank IDDB01014
HMDB IDHMDB0015149
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkBalsalazide
Chemspider ID10662422
ChEBI ID267413
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Eckardt C. G. Wolf, Nageib Mohamed, Bhaskar Reddy Guntoori, “Safe process for the preparation of balsalazide.” U.S. Patent US07271253, issued September 18, 2007.

MSDSNot Available
General References
1. Ragunath K, Williams JG: Review article: balsalazide therapy in ulcerative colitis. Aliment Pharmacol Ther. 2001 Oct;15(10):1549-54.
2. Wiggins JB, Rajapakse R: Balsalazide: a novel 5-aminosalicylate prodrug for the treatment of active ulcerative colitis. Expert Opin Drug Metab Toxicol. 2009 Oct;5(10):1279-84. doi: 10.1517/17425250903206996.