2-hydroxy-5-[(E)-2-(4-{[(2H4)pyridin-2-yl]sulfamoyl}phenyl)diazen-1-yl]benzoic acid

• ChemBase ID: 177988
• Molecular Formular: C18H14N4O5S
• Molecular Mass: 398.39256
• Monoisotopic Mass: 398.06849057
• SMILES: c1(ccc(c(c1)C(=O)O)O)/N=N/c1ccc(cc1)S(=O)(=O)Nc1ncccc1
• Canonical SMILES: OC(=O)c1cc(/N=N/c2ccc(cc2)S(=O)(=O)Nc2ccccn2)ccc1O
• InChI: InChI=1S/C18H14N4O5S/c23-16-9-6-13(11-15(16)18(24)25)21-20-12-4-7-14(8-5-12)28(26,27)22-17-3-1-2-10-19-17/h1-11,23H,(H,19,22)(H,24,25)/b21-20+
• InChIKey: NCEXYHBECQHGNR-QZQOTICOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxy-5-[(E)-2-(4-{[(^2H₄)pyridin-2-yl]sulfamoyl}phenyl)diazen-1-yl]benzoic acid
• IUPAC Traditional name: 2-hydroxy-5-[(E)-2-(4-{[(^2H₄)pyridin-2-yl]sulfamoyl}phenyl)diazen-1-yl]benzoic acid
• Synonyms: 2-Hydroxy-5-[[4-[(2-pyridinylamino-d4)sulfonyl]phenyl]azo]benzoic Acid; 5-[[p-(2-Pyridylsulfamoyl-d4)phenyl]azo]salicylic Acid; 5-[p-(2-Pyridylsulfamyl-d4)phenylazo]salicylic Acid; Azopyrin-d4; Azopyrine-d4; Azulfidine-d4; Azulfidine EN-d4; Benzosulfa-d4; Colo-Pleon-d4; NSC 203730; Reupirin-d4; Salazopyridin-d4; Salazopyrin-d4; Salazopyrine-d4; Salazosulfapyridin-d4; Salazosulfapyridine-d4; Salicylazosulfapyridine-d4; Salisulf-d4; Sulfasalazin-d4; Sulphasalazine-d4; Sulfasalazine-d4

Database IDs

• CAS Number: 1346606-50-5
• PubChem SID: 164233898
• PubChem CID: 71752289

CALCULATED PROPERTIES

• Acid pKa: 3.2977388
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): 1.9754564
• LogD (pH = 7.4): 0.2490507
• Log P: 3.9374347
• Molar Refractivity: 104.6029 cm^3
• Polarizability: 38.571667 Å^3
• Polar Surface Area: 141.31 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S699089

Labelled Sulfasalazine (S699084). An anti-inflammatory (gastrointestinal). Sulfasalazine has been used in granulomatous colitis.

REFERENCES

• Schroder, H., et al.: Clin. Pharmacol. Ther.,13, 539 (1972)
• McDonnell, J.P., et al.: Anal. Profiles Drug Subs., 5, 515 (1972)
• Klotz, U., et al.: Clin. Pharmacokinet.,10, 285 (1972)