Another simpler way of the synthesis of cefuroxime is by direct acylation of 7-amino-3-aminocarbonyloxymethyl-3-cefem-4-carboxylic acid (184.108.40.206), which is isolated from the cultural fluid of Streptomyces lactamdurans, using syn-2-methoxyamino-2-(2-furyl)acetic acid chloride, which is synthesized by reacting the corresponding acid with phosphorous pentachloride [110,111].
Cefuroxime acts bactericidally. It has a narrow spectrum of antimicrobial action. It is resistant to beta-lactamase action. It is highly active with respect to Gram-negative microorganisms (intestinal and hemophilial bacilli, salmonella, shigella, enterobacteria, and gonococci). It is also active with respect to Gram-positive microorganisms (staphylococci, streptococci). It is inactive with respect to various types of Pseudomonas, most strains of enterococci, many strains of Enterobacter cloacae, methylcillin-resistant staphylococci, and L. monocytogenes.
It is used for bacterial infections caused by microorganisms that are sensitive to the drug. These may be abdominal and gynecological infections, sepsis, meningitis, endocarditis, infections of the urinary and respiratory tracts, bones, joints, skin, and soft tissues. It is widely used for pneumonia as well as bacterial meningitis in children, and for post-operational infectious complications. Synonyms of this drug are ceftin, zinacef, curoxim, kefox, and many others.
Cefamandole: Cefamandole, 7-D-mandelamido-3-[[(1-methyl-1H-tetrazol-5-yl)thio] methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (220.127.116.11), is synthesized from 7-aminocephalosporanic acid.
Protecting free amino group in 7-aminocephalosporanic acid by formylation with formic acid in the presence of acetic anhydride produces 7-formamidocephalosporanic acid (18.104.22.168). The acetoxy group of this compound is replaced by a reaction with 1-methyl-1,2,3,4-tetrazol-5-thiol, after which the N-formyl protection is removed by hydrochloric acid, giving 7-amino-3-(1-methyl-1,2,3,4-tetrazol-5-yl)-thiomethyl-3-cefem-4-carboxylic acid (22.214.171.124). Reacting this with a mixed anhydride synthesized from mandelic acid and phosgene gives the desired cefamandole (126.96.36.199) [112-119].
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