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

J. Jensen; Claus Cornett; C. E. Olsen; J. Tjornelund; S. H. Hansen

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

J. Jensen, Claus Cornett, C. E. Olsen, J. Tjornelund, S. H. Hansen

31 Citations (Scopus)

Abstract

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.

Original language	English
Journal	International Journal of Pharmaceutics
Volume	88
Issue number	1-3
Pages (from-to)	177-187
Number of pages	11
ISSN	0378-5173
Publication status	Published - 1992

Cite this

@article{d2c8c175a19f4cc7a004851a6bb47bab,

title = "Identification of major degradation products of 5-aminosalicylic acid formed in aqueous solutions and in pharmaceuticals",

abstract = "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.",

keywords = "5-aminosalicylic acid mesalazine oxidative polymerization degradation product nmr structure determination inflammatory bowel-disease stability metabolites mechanism",

author = "J. Jensen and Claus Cornett and Olsen, {C. E.} and J. Tjornelund and Hansen, {S. H.}",

year = "1992",

language = "English",

volume = "88",

pages = "177--187",

journal = "International Journal of Pharmaceutics",

issn = "0378-5173",

publisher = "Elsevier",

number = "1-3",

}

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

SN - 0378-5173

VL - 88

SP - 177

EP - 187

JO - International Journal of Pharmaceutics

JF - International Journal of Pharmaceutics

IS - 1-3

ER -