disodium 5-(2-{4-[(2-carboxylatoethyl)carbamoyl]phenyl}diazen-1-yl)-2-hydroxybenzoate hydrate

• ChemBase ID: 154786
• Molecular Formular: C17H15N3Na2O7
• Molecular Mass: 419.29644
• Monoisotopic Mass: 419.0705384
• SMILES: c1cc(ccc1C(=O)NCCC(=O)[O-])/N=N/c1ccc(c(c1)C(=O)[O-])O.O.[Na+].[Na+]
• Canonical SMILES: [O-]C(=O)CCNC(=O)c1ccc(cc1)/N=N/c1ccc(c(c1)C(=O)[O-])O.O.[Na+].[Na+]
• InChI: InChI=1S/C17H15N3O6.2Na.H2O/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);;;1H2/q;2*+1;/p-2
• InChIKey: ZZZXQZHSFPVNCR-UHFFFAOYSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium 5-(2-{4-[(2-carboxylatoethyl)carbamoyl]phenyl}diazen-1-yl)-2-hydroxybenzoate hydrate
• IUPAC Traditional name: disodium 5-(2-{4-[(2-carboxylatoethyl)carbamoyl]phenyl}diazen-1-yl)-2-hydroxybenzoate hydrate
• Synonyms: 5-[4-(2-Carboxyethylcarbamoyl)phenylazo]salicylic acid disodium salt hydrate; Balsalazide disodium salt hydrate

Database IDs

• CAS Number: 213594-60-6(anhydrous)
• MDL Number: MFCD18632541
• PubChem SID: 162248924
• PubChem CID: 57086142

CALCULATED PROPERTIES

• Acid pKa: 3.0649273
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.0041051
• LogD (pH = 7.4): -3.6215541
• Log P: 3.1724694
• Molar Refractivity: 116.0474 cm^3
• Polarizability: 33.316666 Å^3
• Polar Surface Area: 154.31 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: nwg
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99% (HPLC)
• Empirical Formula (Hill Notation): C17H13N3Na2O6 · xH2O

DETAILS

Sigma Aldrich - B5438

Biochem/physiol Actions
Balsalazide has antioxidative and anti-inflammatory properties. It inhibits superoxide production and was found to scavenge hypochlorite radicals.1 Balsalazide was shown to inhibit lipid peroxidation in rat intestinal mucosa.2 It was also shown to inhibit azoxymethane-induced colon carcinogenesis.3 In vivo, basalazide is cleaved through azoreduction to produce 4-aminobenzoyl-β-alanine, an inert carrier moiety, and 5-aminosalicylic acid (5-ASA).