NEW METABOLITES OF THE DRUG 5-AMINOSALICYLIC ACID .2. N-FORMYL-5-AMINOSALICYLIC ACID

J. Tjornelund; S. H. Hansen; Claus Cornett

NEW METABOLITES OF THE DRUG 5-AMINOSALICYLIC ACID .2. N-FORMYL-5-AMINOSALICYLIC ACID

J. Tjornelund, S. H. Hansen, Claus Cornett

13 Citationer (Scopus)

Abstract

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.

Originalsprog	Udefineret/Ukendt
Tidsskrift	Xenobiotica
Vol/bind	21
Udgave nummer	5
Sider (fra-til)	605-612
Antal sider	8
ISSN	0049-8254
Status	Udgivet - 1991

Emneord

4-formylaminoantipyrine biotransformation 1-nitropyrene aminopyrine invivo rat

Citationsformater

@article{afa60896ed704295b78f393fb2c2455b,

title = "NEW METABOLITES OF THE DRUG 5-AMINOSALICYLIC ACID .2. N-FORMYL-5-AMINOSALICYLIC ACID",

abstract = "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.",

keywords = "4-formylaminoantipyrine biotransformation 1-nitropyrene aminopyrine invivo rat",

author = "J. Tjornelund and Hansen, {S. H.} and Claus Cornett",

year = "1991",

language = "Udefineret/Ukendt",

volume = "21",

pages = "605--612",

journal = "Xenobiotica",

issn = "0049-8254",

publisher = "Taylor & Francis",

number = "5",

}

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

SN - 0049-8254

VL - 21

SP - 605

EP - 612

JO - Xenobiotica

JF - Xenobiotica

IS - 5

ER -