NEW METABOLITES OF THE DRUG 5-AMINOSALICYLIC ACID .2. N-FORMYL-5-AMINOSALICYLIC ACID
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NEW METABOLITES OF THE DRUG 5-AMINOSALICYLIC ACID .2. N-FORMYL-5-AMINOSALICYLIC ACID. / Tjornelund, J.; Hansen, S. H.; Cornett, Claus.
In: Xenobiotica, Vol. 21, No. 5, 1991, p. 605-612.Research output: Contribution to journal › Journal article › peer-review
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TY - JOUR
T1 - NEW METABOLITES OF THE DRUG 5-AMINOSALICYLIC ACID .2. N-FORMYL-5-AMINOSALICYLIC ACID
AU - Tjornelund, J.
AU - Hansen, S. H.
AU - Cornett, Claus
PY - 1991
Y1 - 1991
N2 - 1. A new metabolite of the drug 5-aminosalicylic acid (5-ASA) has been found in urine from pigs and in plasma of humans. The metabolite has been isolated from pig urine using an XAD-2 column and purified using preparative h.p.l.c. 2. The metabolite has been identified as N-formyl-5-ASA (5-formamidosalicylic acid) using H-1- and C-13-n.m.r. spectrometry and mass spectroscopy and the structure was confirmed by chemical synthesis. 3. N-Formyl-5-ASA is stable in human plasma and in potassium phosphate buffers between pH 3.0 and 9.0. It is hydrolysed below pH 3.0. 4. N-Formyl-5-ASA was readily formed in rat liver homogenate when 5-ASA and N-formyl-L-kynurenine were added. Thus N-formyl-5-ASA might be formed by the actions of formamidase in vivo. 5. N-Formyl-5-ASA has been found in human plasma from healthy volunteers dosed i.v. with 5-ASA (250 mg). N-beta-D-glucopyranosyl-5-ASA, N-acetyl-5-ASA and N-formyl-5-ASA were quantified in human plasma using a h.p.l.c. assay.
AB - 1. A new metabolite of the drug 5-aminosalicylic acid (5-ASA) has been found in urine from pigs and in plasma of humans. The metabolite has been isolated from pig urine using an XAD-2 column and purified using preparative h.p.l.c. 2. The metabolite has been identified as N-formyl-5-ASA (5-formamidosalicylic acid) using H-1- and C-13-n.m.r. spectrometry and mass spectroscopy and the structure was confirmed by chemical synthesis. 3. N-Formyl-5-ASA is stable in human plasma and in potassium phosphate buffers between pH 3.0 and 9.0. It is hydrolysed below pH 3.0. 4. N-Formyl-5-ASA was readily formed in rat liver homogenate when 5-ASA and N-formyl-L-kynurenine were added. Thus N-formyl-5-ASA might be formed by the actions of formamidase in vivo. 5. N-Formyl-5-ASA has been found in human plasma from healthy volunteers dosed i.v. with 5-ASA (250 mg). N-beta-D-glucopyranosyl-5-ASA, N-acetyl-5-ASA and N-formyl-5-ASA were quantified in human plasma using a h.p.l.c. assay.
KW - 4-formylaminoantipyrine biotransformation 1-nitropyrene aminopyrine invivo rat
M3 - Tidsskriftartikel
VL - 21
SP - 605
EP - 612
JO - Xenobiotica
JF - Xenobiotica
SN - 0049-8254
IS - 5
ER -
ID: 38062419