Isomerization of ceftibuten in aqueous solution.

Abstract:

:The isomerization reactions of ceftibuten and ceftibuten-related compounds in aqueous solution were investigated to estimate the substitution effect on the isomerization reaction and identify the three proximal dissociation constants of ceftibuten kinetically from the pH-rate profiles. The isomerization reaction of ceftibuten-related compounds was influenced by the substituents near the double bond at the C7-side chain, and the electron-withdrawing substituent was found to increase the isomerization rate. Ceftibuten isomerized at the C7-side chain, and the isomerization rate was influenced by the dissociation of the C7-side chain carboxylic acid and aminothiazole in the acidic pH region. The dissociation constants of ceftibuten were assigned by comparing the isomerization rates of ceftibuten with its related compounds at various pH conditions, and the pKas 2.3, 3.2, and 4.5 were attributed to the 4-carboxylic acid, 7-carboxylic acid, and 7-aminothiazole, respectively.

journal_name

J Pharm Sci

authors

Hashimoto N,Hirano K

doi

10.1021/js980048z

subject

Has Abstract

pub_date

1998-09-01 00:00:00

pages

1091-6

issue

9

eissn

0022-3549

issn

1520-6017

pii

S0022-3549(15)50637-0

journal_volume

87

pub_type

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