Cefuroxime Axetil (Ceftin^®): A Brief Review

Abstract

KEY WORDS cefuroxime axetil; antimicrobial; uncomplicated gonorrhea efuroxime axetil (Ceftin(R), Glaxo Wellcome, Research Triangle Park, NC) is the oral prodrug formulation of the injectable antibiotic cefuroxime sodium. It has essentially the same antibacterial activity as its parent moiety, making cefuroxime the only second-generation cephalosporin with both an intravenous and oral formulation. STRUCTURE AND DERIVATION Cefuroxime axetil is the 1-acetoxyethyl ester of cefuroxime. The axetil salt renders the molecule more lipophilic, thus allowing enhanced oral absorption. Once cefuroxime axetil reaches the intestinal mucosa and portal blood flow it rapidly undergoes de-esterification to yield the active parent compound cefuroxime. MECHANISM OF ACTION Cefuroxime axetil is a second-generation cephalosporin that contains the classic [3-1actam ring struc

Molecular Structure of Cefuroxime Axetil Complexes with α-, β-, γ-, and 2-Hydroxypropyl-β-Cyclodextrins: Molecular Simulations and Raman Spectroscopic and Imaging Studies

“…In the pharmaceutical formulation studies, CDs have mostly been applied as complexing compounds to increase the water solubility and to improve the bioavailability and stability of poorly soluble drugs, for example, cephalosporins [24], including cefuroxime. Cefuroxime axetil (CA), an 1-acetoxyethyl ester of cefuroxime (prodrug), is a broad spectrum second-generation semisynthetic cephalosporin comprising a β-lactam ring [25], being effectively absorbed from the gastrointestinal tract due to its lipophilicity and subsequently de-esterified to cefuroxime [26]. The antibacterial activity of cefuroxime in vivo is the result of its capacity to bind target proteins located in the bacterial cell wall, which leads to the inhibition of cell wall synthesis, hence the bacteria lose their ability to divide and mature.…”

Preparation and evaluation of cefuroxime axetil gastro-retentive floating drug delivery system via hot melt extrusion technology

“…However, upon oral administration, CA is mainly absorbed in the proximal region of the GI tract and undergoes rapid hydrolysis to form cefuroxime in the presence of non-specific esterase enzymes in the intestinal mucosa and blood ( Figure 1A) (Sommers et al, 1984). Although the 1-acetoxyethyl ester group of CA increases lipophilicity of cefuroxime, de-esterification due to esterase enzymes prior to absorption in the intestinal fluids leads to low permeation across the intestinal mucosa (Barrett et al, 1997;Harding et al, 1984;Leder and Carson, 1997). CA is poorly soluble, and exhibits greater bioavailability in the presence of lipid-rich foods due to lower specificity of esterase enzymes toward CA in the intestine (Finn et al, 1987;Williams and Harding, 1984).…”