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Isomerization of ceftibuten in aqueous solution

N Hashimoto¹, K Hirano

¹Shionogi Research Laboratories, Shionogi & Co., Ltd., Sagisu, Fukushima-ku, Osaka 553, Japan.

Journal of Pharmaceutical Sciences

|September 2, 1998

Summary

The study investigated ceftibuten isomerization, finding that electron-withdrawing groups accelerate the reaction. Researchers identified three key dissociation constants (pKas) for ceftibuten, crucial for understanding its stability and behavior.

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Area of Science:

Medicinal Chemistry
Organic Chemistry
Physical Chemistry

Background:

Ceftibuten is a third-generation cephalosporin antibiotic.
Understanding its isomerization is vital for drug stability and formulation.
Previous studies have not fully elucidated the kinetic factors influencing ceftibuten isomerization.

Purpose of the Study:

To investigate the isomerization reactions of ceftibuten and related compounds in aqueous solution.
To determine the effect of substituents on the isomerization rate.
To kinetically identify the three proximal dissociation constants (pKas) of ceftibuten.

Main Methods:

Kinetic analysis of isomerization reactions across a range of pH conditions.
Comparison of isomerization rates between ceftibuten and structurally related compounds.
pH-rate profile analysis to determine dissociation constants.

Main Results:

Isomerization rate is influenced by substituents at the C7-side chain double bond.
Electron-withdrawing substituents increase the isomerization rate.
Three dissociation constants were identified: pKa 2.3 (4-carboxylic acid), pKa 3.2 (7-carboxylic acid), and pKa 4.5 (7-aminothiazole).

Conclusions:

The C7-side chain substituents significantly impact ceftibuten isomerization kinetics.
The dissociation of the 7-carboxylic acid and 7-aminothiazole groups influences isomerization in acidic conditions.
The identified pKas provide critical insights into ceftibuten's chemical behavior and stability.