Metabolic fate of N-butyl-N-(4-hydroxybutyl)nitrosamine in the rat.

Abstract

The metabolic fate of N-butyl-N-(4-hydroxybutyl)nitrosamine (BBN) was studied in the rat, to investigate the possibility of a relationship between urinary metabolites and organotropic carcinogenicity to the urinary bladder of this N-nitrosamine. The principal urinary metabolite of BBN was identified as N-butyl-N-(3-carboxypropyl)nitrosamine (BCPN). Several minor metabolites characterized were transformation products of BCPN formed by beta-oxidation according to the Knoop mechanism, i.e., N-butyl-N-(2-hydroxy-3-carboxy-propyl)nitrosamine, N-butyl-N-(carboxymethyl)nitrosamine and N-butyl-N-(2-oxopropyl)nitrosamine; glucuronic acid conjugates of BBN and BCPN were also detected. No BBN was detected in the urine. A possible correlation of the urinary excretion of BCPN with selective induction of bladder tumors by BBN in rats is discussed in relation to the carcinogenic action of BCPN.

• Authors: E Suzuki, M Okada
• Journal: Gan (Gan) Vol. 71 Issue 6 Pg. 856-62 (Dec 1980) ISSN: 0016-450X [Print] Japan
• PMID: 7274630 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Nitrosamines
• Butylhydroxybutylnitrosamine

Topics

• Animals
• Biotransformation
• Butylhydroxybutylnitrosamine (isolation & purification, metabolism)
• Chromatography, Thin Layer
• Hydrolysis
• Male
• Methylation
• Neoplasms, Experimental (chemically induced)
• Nitrosamines (metabolism)
• Rats
• Urinary Bladder Neoplasms (chemically induced)