TY - JOUR

T1 - Identification of major degradation products of 5-aminosalicylic acid formed in aqueous solutions and in pharmaceuticals

AU - Jensen, J.

AU - Cornett, Claus

AU - Olsen, C. E.

AU - Tjornelund, J.

AU - Hansen, S. H.

PY - 1992

Y1 - 1992

N2 - The formation of four major degradation products of 5-aminosalicylic acid (5-ASA) in buffered solutions at pH 7.0 was demonstrated by gradient HPLC analysis. The isolation and structural elucidation of the resulting degradation products showed that the degradation of 5-ASA led to the formation of polymeric species by oxidative self-coupling of 5-ASA moieties. These results indicate that the degradation of 5-ASA follows the same mechanism as observed for the autooxidation of 4-aminophenol and 1,4-phenylenediamine. Some of the identified degradation products were found in 5-ASA-containing pharmaceuticals, which had not been stored as prescribed, but in diffuse daylight for up to 2 years.

AB - The formation of four major degradation products of 5-aminosalicylic acid (5-ASA) in buffered solutions at pH 7.0 was demonstrated by gradient HPLC analysis. The isolation and structural elucidation of the resulting degradation products showed that the degradation of 5-ASA led to the formation of polymeric species by oxidative self-coupling of 5-ASA moieties. These results indicate that the degradation of 5-ASA follows the same mechanism as observed for the autooxidation of 4-aminophenol and 1,4-phenylenediamine. Some of the identified degradation products were found in 5-ASA-containing pharmaceuticals, which had not been stored as prescribed, but in diffuse daylight for up to 2 years.

KW - 5-aminosalicylic acid mesalazine oxidative polymerization degradation product nmr structure determination inflammatory bowel-disease stability metabolites mechanism

M3 - Journal article

VL - 88

SP - 177

EP - 187

JO - International Journal of Pharmaceutics

JF - International Journal of Pharmaceutics

SN - 0378-5173

IS - 1-3

ER -