Enterohepatic circulation of 2,4-dinitrobenzaldehyde, a mutagenic metabolite of 2,4-dinitrotoluene, in male Wistar rat.
1. The major biliary metabolite of 2,4-dinitrotoluene (2,4-DNT) in male Wistar rat was 2,4-dinitrobenzyl alcohol glucuronide and the minor metabolites were 2,4-dinitrobenzyl alcohol, 2,4-dinitrobenzaldehyde, 2-acetylamino-4-nitrotoluene, 4-amino-2-nitro(2-amino-4-nitro)benzyl alcohol sulphate, 2,4-dinitrobenzoic acid, 2,4-diacetylaminobenzoic acid and 2-amino-4-nitrobenzoic acid. 2. 2,4-Dinitrobenzyl alcohol, 2,4-dinitrobenzaldehyde, 2,4-dinitrobenzyl alcohol glucuronide and 4-amino-2-nitro(2-amino-4-nitro)benzyl sulphate were excreted in the bile of male Wistar rat dosed with 2,4-dinitrobenzyl alcohol. 3. 2,4-Dinitrobenzaldehyde, 2,4-dinitrobenzyl alcohol, 2,4-dinitrobenzyl glucuronide, 4-amino-2-nitro(2-amino-4-nitro)benzyl alcohol sulphate and 2,4-diacetylaminobenzoic acid were excreted in the bile of male Wistar rat dosed with 2,4-dinitrobenzaldehyde. 4. These results indicate that the common biliary metabolites of 2,4-DNT, 2,4-dinitrobenzyl alcohol and 2,4-dinitrobenzaldehyde are 2,4-dinitrobenzyl alcohol and its glucuronide, and 2,4-dinitrobenzaldehyde, and suggest the enterohepatic circulation of 2,4-dinitrobenzaldehyde in the metabolism of 2,4-DNT.
Sayama
M
M
Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Japan.
Mori
M
M
Ishida
M
M
Okumura
K
K
Kozuka
H
H
D000818:Animals; D001547:Benzaldehydes / Q000378:metabolism*; D001592:Benzyl Alcohols / Q000378:metabolism; D001646:Bile / Q000378:metabolism; D001711:Biotransformation; D002851:Chromatography, High Pressure Liquid; D004136:Dinitrobenzenes / Q000378:metabolism*; D004764:Enterohepatic Circulation; D006868:Hydrolysis; D008297:Male; D009578:Nitrobenzenes / Q000378:metabolism*; D010659:Phenylhydrazines; D051381:Rats; D011919:Rats, Inbred Strains
D001547:Benzaldehydes; D001592:Benzyl Alcohols; D004136:Dinitrobenzenes; D009578:Nitrobenzenes; D010659:Phenylhydrazines; C030299:phenylhydrazine; C016403:2,4-dinitrotoluene; C053732:2,4-dinitrobenzaldehyde