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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:31:39 UTC
HMDB IDHMDB15149
Secondary Accession NumbersNone
Metabolite Identification
Common NameBalsalazide
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.
Structure
Thumb
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
Balsalazide disodiumHMDB
Chemical FormulaC17H15N3O6
Average Molecular Weight357.3175
Monoisotopic Molecular Weight357.096085227
IUPAC Name5-[(E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]-2-hydroxybenzoic acid
Traditional Namebalsalazide
CAS Registry Number80573-04-2
SMILES
OC(=O)CCNC(=O)C1=CC=C(C=C1)\N=N\C1=CC=C(O)C(=C1)C(O)=O
InChI Identifier
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+
InChI KeyInChIKey=IPOKCKJONYRRHP-FMQUCBEESA-N
Chemical Taxonomy
DescriptionThis compound 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 bezene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzobenzenes
Sub ClassNot Available
Direct ParentAzobenzenes
Alternative Parents
Substituents
  • Azobenzene
  • Beta amino acid or derivatives
  • Salicylic acid
  • Salicylic acid or derivatives
  • Hydroxybenzoic acid
  • Benzoic acid
  • Benzoic acid or derivatives
  • Benzamide
  • Benzoyl
  • Phenol
  • Benzenoid
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azo compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Ulcer Agents
  • Gastrointestinal Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.21e-02 g/LNot Available
LogP1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.062 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity94.37 m3·mol-1ChemAxon
Polarizability35.98 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01014
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01014
  • Not Applicable
details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01014
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10662422
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBalsalazide
NuGOwiki LinkHMDB15149
Metagene LinkHMDB15149
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID267413
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [19743890 ]
  2. Ragunath K, Williams JG: Review article: balsalazide therapy in ulcerative colitis. Aliment Pharmacol Ther. 2001 Oct;15(10):1549-54. [11563993 ]

Enzymes

General function:
Involved in metal ion binding
Specific function:
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name:
ALOX5
Uniprot ID:
P09917
Molecular weight:
77982.595
References
  1. 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. [19743890 ]
  2. Rask-Madsen J, Bukhave K, Laursen LS, Lauritsen K: 5-Lipoxygenase inhibitors for the treatment of inflammatory bowel disease. Agents Actions. 1992;Spec No:C37-46. [1359745 ]
General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. 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. [19743890 ]
  4. Stolfi C, Fina D, Caruso R, Caprioli F, Sarra M, Fantini MC, Rizzo A, Pallone F, Monteleone G: Cyclooxygenase-2-dependent and -independent inhibition of proliferation of colon cancer cells by 5-aminosalicylic acid. Biochem Pharmacol. 2008 Feb 1;75(3):668-76. Epub 2007 Sep 29. [17981262 ]
  5. Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [12950415 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. 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. [19743890 ]
  4. Allgayer H: Review article: mechanisms of action of mesalazine in preventing colorectal carcinoma in inflammatory bowel disease. Aliment Pharmacol Ther. 2003 Sep;18 Suppl 2:10-4. [12950415 ]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]
General function:
Involved in DNA binding
Specific function:
Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to a promoter element in the gene for acyl-CoA oxidase and activates its transcription. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis
Gene Name:
PPARG
Uniprot ID:
P37231
Molecular weight:
57619.6
References
  1. Tursi A: Balsalazide in treating colonic diseases. Expert Opin Drug Metab Toxicol. 2009 Dec;5(12):1555-63. [19708827 ]
  2. Iacucci M, de Silva S, Ghosh S: Mesalazine in inflammatory bowel disease: a trendy topic once again? Can J Gastroenterol. 2010 Feb;24(2):127-33. [20151072 ]
  3. Desreumaux P, Ghosh S: Review article: mode of action and delivery of 5-aminosalicylic acid - new evidence. Aliment Pharmacol Ther. 2006 Sep;24 Suppl 1:2-9. [16939423 ]
  4. Linard C, Gremy O, Benderitter M: Reduction of peroxisome proliferation-activated receptor gamma expression by gamma-irradiation as a mechanism contributing to inflammatory response in rat colon: modulation by the 5-aminosalicylic acid agonist. J Pharmacol Exp Ther. 2008 Mar;324(3):911-20. Epub 2007 Dec 12. [18077625 ]