JBC, Vol. 251, Issue 6, 1646-1652, Mar, 1976
In vivo metabolism of 4'-deoxypyridoxine in rat and man
S. P. Coburn and J. D. Mahuren
In rats 80 to 95% of 4'-deoxypyridoxine administered intraperitoneally,
intravenously, intramuscularly, or subcutaneously was excreted in the urine
within 7.5 hours. Orally administered deoxypyridoxine was also rapidly
eliminated. Over one-half of the excreted material appeared as
deoxypyridoxine-3-(hydrogen sulfate) and the remainder as unchanged
deoxypyridoxine. Tissue concentrations of deoxypyridoxine 5'phosphate were
comparable to those of pyridoxal 5'phosphate. In normal men about 50% of a
single oral dose (3 to 7.5 mg/kg of body weight) appeared in the urine
within 6 hours. 4'Deoxy-5-pyridoxic acid accounted for 50 to 100% of the
excreted material. The remainder was unchanged deoxypyridoxine. No
deoxypyridoxine-3-(hydrogen sulfate) was detected in human urine and no
4'-deoxy-5-pyridoxic acid was found in rat urine. Deoxypyridoxine
5'-phosphate was not detected in the urine of either species. The
complexity of deoxypyridoxine metabolism indicated by these data suggests
the use of caution in extrapolating data obtained with deoxypyridoxine to
B6 metabolism in the absence of deoxypyridoxine, and particularly in
extrapolating results from the rat to man. Synthesis for
4'-deoxypyridoxine-3-(ethyl carbonate), 4'-deoxypyridoxine 5'-acetate,
4'-deoxy-3-0-(2-sulfoethyl)-pyridoxine, and the metabolites are presented.
These synthesis were facilitated by using ethylchloroformate conjugates and
N-methylpiperazine hydrolysis to block and unblock the phenol group.
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