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Balsalazide

July 24, 2017
Common Name

Balsalazide 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 licerative colitis. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source (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 Formlia

C17H15N3O6 Average Molecliar Weight

357.3175 Monoisotopic Molecliar Weight

357.096085227 IUPAC Name

5-[(E)-2-{4-[(2-carboxyethyl)carbamoyl]phenyl}diazen-1-yl]-2-hydroxybenzoic acid Traditional Name

balsalazide CAS Registry Number

80573-04-2 SMILES

OC(=O)CCNC(=O)C1=CC=C(C=C1)N=NC1=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 Key

IPOKCKJONYRRHP-FMQUCBEESA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as azobenzenes. These are organonitrogen aromatic compounds that contain a central azo group, where each nitrogen atom is conjugated to a benzene ring. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Azobenzenes Direct Parent

Azobenzenes Alternative Parents

  • Beta amino acids and derivatives
  • Salicylic acids
  • Benzamides
  • Benzoic acids
  • Benzoyl derivatives
  • 1-hydroxy-2-unsubstituted benzenoids
  • Dicarboxylic acids and derivatives
  • Vinylogous acids
  • Secondary carboxylic acid amides
  • Azo compounds
  • Carboxylic acids
  • Propargyl-type 1,3-dipolar organic compounds
  • Carbonyl compounds
  • Organic oxides
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • 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

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • monohydroxybenzoic acid (CHEBI:267413 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Ulcer Agents
  • Gastrointestinal Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility6.21e-02 g/LNot Available LogP1.3Not Available

    Predicted Properties

    Property Value Source 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01014

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01014

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-3 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-1 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01014 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    10662422 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Balsalazide NuGOwiki Link

    HMDB15149 Metagene Link

    HMDB15149 METLIN ID

    Not Available PubChem Compound

    Not Available PDB ID

    Not Available ChEBI ID

    267413

    Product: THZ2

    References Synthesis Reference Not 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. doi: 10.1517/17425250903206996. [PubMed:19743890 ]
    2. Ragunath K, Williams JG: Review article: balsalazide therapy in ulcerative colitis. Aliment Pharmacol Ther. 2001 Oct;15(10):1549-54. [PubMed: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. doi: 10.1517/17425250903206996. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. doi: 10.1517/17425250903206996. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. doi: 10.1517/17425250903206996. [PubMed: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. [PubMed:12950415 ]
    5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed: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. doi: 10.1517/17425250903228842. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:18077625 ]

    PMID: 19150877

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