Stability, bactericidal activity, vitamin B6 activity and gastrointestinal absorption of benzoic acid esters of pyridoxine.

alpha 4-O-Benzoyl-pyridoxine (PN-4'MB) and alpha 5-O-benzoyl-pyridoxine (PN-5'MB) were hydrolyzed in 10% aqueous solution of acetone at pH 1-4. They were hydrolyzed obeying apparent first-order kinetics. In the pH range of 1-7, PN-4'MB was hydrolyzed 10 times faster than PN-5'-MB. At pH 7-12, an interconversion between the two derivatives was observed. They were bactericidal against Escherichia coli and Bacillus subtilis and prevented severe convulsions induced in mouse by 4'-methoxypyridoxine, a potent antagonist of vitamin B6. PN-4'MB was hydrolyzed with the homogenate of rat liver more easily than PN-5'MB. The metabolite of PN-MBs in man was identified as 4'-pyridoxic acid, i.e., a principal metabolite of PN, using high-performance liquid chromatography. The amount of urinary excretion of 4'-pyridoxic acid in 10 hr after oral administration of PN-4'MB or PN-5'MB was as large as that of PN.