Cefuroxime

Therapeutics. Compounds containing the furan or tetrahydrofuran ring are biologically active and are present in a number of pharmaceutical products. Eurfurjdamine [617-89-0] is an intermediate in the diuretic, furosemide. Tetrahydrofurfurylamine [4795-29-3] may also have pharmaceutical applications. 5-(E)imethyiaininomethyi)furfuryi alcohol [15433-79-17 is an intermediate in the preparation of ranitidine, which is used for treating ulcers. 2-Acet5dfuran [1192-62-7] prepared from acetic anhydride and furan is an intermediate in the synthesis of cefuroxime, a penicillin derivative. 2-Euroic acid is prepared by the oxidation of furfural. Both furoic acid [88-14-2] and furoyl chloride [527-69-5] are used as pharmaceutical intermediates. 

Cefuroxime (35) is effective against community-acquired pneumonia in which ampicillin-resistant Haemophilus influence is the probable etiologic agent. Cefoxitin (23) is used to treat mixed aerobic—anaerobic infections including pelvic infections, intra-abdorninal infections, and nosocomial aspiration pneumonia. Cefonicid (31), because of its long half-life has been used in a once-a-day regimen to treat a variety of mild to moderate infections including community-acquired pneumonias, urinary tract infections, and infections of the skin and soft tissue (132,215). 

Cephalosporins first entered the marketplace in 1964, when cephalothin (27) and cephaloridine (51), which are both injectable, were launched. By the late 1970s, the injectable cephalosporins had become important therapeutic agents in the hospitals. Also in 1964 the first oral cephalosporin, cephaloglycin [3577-01 -3] C gH N OgS, was launched only to be displaced by the end of the year by cephalexin (12). For years cephalexin was the leading oral cephalosporin on the market. It has since been displaced by cefaclor (13). With the advent of the more -lactamase stable cephalosporins such as cefoxitin (23) and cefuroxime (35), and the more potent agents such as cefotaxime (36) and other third-generation compounds, cephalosporins now dominate the antibiotic market worldwide. 

Another important enzymatic process in the production of 7-ADCA, for use in the production of semi-synthetic cephalosporins, is the hydrolysis of 7-aminocephalosporanic add (7-ACA) by the enzyme acetyl esterase. This process, again using immobilisation techniques, is illustrated in Figure 6.16. Hie deacylated product can be used, for example, as an intermediate in the production of the important oral cephalosporin cefuroxime. We will return to cephalosporin antibiotics later in this chapter. 

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