Abstract
Ceftibuten, C15H14N4O6S2, with the systematic name (6R,7R)-7-{[(Z)-2-(2-amino-1,3-thia-zol-4-yl)-4-carb-oxy-but-2-eno-yl]amino}-8-oxo-5-thia-1-aza-bicyclo-[4.2.0]oct-2-ene-2-carb-oxy-lic acid, is a third generation, orally administered cephalosporin anti-biotic with broad anti-microbial activity and stability against extended spectrum β-lactamases. Ceftibuten can exist in various hydration states and to better understand the location of the water mol-ecules of crystallization and their effect on the structure, the crystal structures of anhydrous (I) and hydrated (II) ceftibuten were determined and both occur as zwitterions with proton transfer from the carboxyl-ate group adjacent to the β-lactam ring to the N atom of the thia-zole ring. The β-lactam ring in (I) is almost planar but the equivalent grouping in (II) is slightly buckled. In the extended structure of (I), O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. In (II), O-H⋯Oc, N-H⋯Oc, O-H⋯Ow, N-H⋯Ow and Ow-H⋯Ow (c = ceftibuten, w = water) hydrogen bonds link the components into a three-dimensional network. A large void space is present within the anhydrous crystal structure that can accommodate between two and three mol-ecules of water.
Highlights
Ceftibuten, originally marketed under the tradename Cedax in the USA, is a third-generation cephalosporin antibiotic with activity against a variety of bacterial strains and resistance to extended spectrum -lactamases (Wiseman & Balfour, 1994; Hamashima et al, 1990)
Ceftibuten can exist in various hydration states and to better understand the location of the water molecules of crystallization and their effect on the structure, the crystal structures of anhydrous (I) and hydrated (II) ceftibuten were determined and both occur as zwitterions with proton transfer from the carboxylate group adjacent to the -lactam ring to the N atom of the thiazole ring
In the extended structure of (I), O—HÁ Á ÁO and N—HÁ Á ÁO hydrogen bonds link the molecules into a three-dimensional network
Summary
Ceftibuten, originally marketed under the tradename Cedax in the USA, is a third-generation cephalosporin antibiotic with activity against a variety of bacterial strains and resistance to extended spectrum -lactamases (Wiseman & Balfour, 1994; Hamashima et al, 1990). Oral administration of ceftibuten is effective for treating urinary tract or respiratory tract infections, including many caused by -lactamase-expressing bacterial strains (Owens et al, 1997). Despite its withdrawal from the US market, because of its effectiveness and stability against -lactamases, renewed interest in ceftibuten for multidrug-resistant urinary tract infections (UTIs) has emerged, and studies are underway investigating oral administration of ceftibuten co-administered with a -lactamase inhibitor as an alternative to hospitalization for complicated UTIs (Veeraraghavan et al, 2021; Chatwin et al, 2021). Despite its long-time commercial availability, to our knowledge no crystal structures of ceftibuten have been previously reported. The structures of anhydrous ceftibuten (I) and hydrated ceftibuten (II) are reported
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