Stability and degradation pattern of cefpirome (HR 810) in aqueous solution.

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Abstract
The stability and degradation pathways of a new semi-synthetic cephalosporin, 1[[(6R, 7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-5H-1-pyrindinium hydroxide, inner salt, 72-(Z)-(O-methyloxime) sulfate (cefpirome sulfate, HR 810), were studied. Cefpiromen in various buffer solutions was allowed to stand at 40.degree.C and its degradation patterns were investigated by higher performance liquid chromatography. Cefpirome was stable in the region of pH 4-7 and slightly unstable beyond this range. In aqueous solution from the neutral to alkaline regions, the produced degradation products were: 1-[[(6R,7S)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-2-carboxy-8-oxo-5-thia-1-azabicyclco[4.2.0]oct-2-en-3-yl]methyl]-6,7-dihydro-5H-1-pyrindinium hydroxide, inner salt, 72-(Z)-(O-methyloxime) (epi-cefpirome); 1-[[(6R,7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-3-en-3-yl]methyl]-6,7-dihydro-5H-1-pyrindinium hydroxide, inner salt, 72-(Z)-(O-methyloxime) (.DELTA.2-cefpirome); 2-[[(2-amino-4-thiazolyl)((Z)-methoxyimino)acetyl]amino]acetaldehye; and 6,7-dihydro-5H-1-pyrindine. On the other hand, 1-[[(6R,7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-2-carboxy-8-oxo-5-thia-1-azabicyclo[4.2.0)oct-2-en-3-yl]methyl]-6,7-dihydro-5H-1-pyrindinium hydroxide, inner salt, 72-(E)-(O-methyloxime) (anti-cefpirome), 2-[[(2-amino-4-thiazolyl)-((Z)-methoxyimino)-acetyl]aminomethyl]-1,2,5,7-tetrahydro-7-oxo-4H-furo[3,4-d]-[1,3]thiazine, and 6,7-dihydro-5H-1-pyrindine were produced in strongly acidic solution or under irradiation by artificial sunlight.

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