Cemandil sodium salt

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Cephalosporin antibacterial.

ChEBI: A cephalosporin prodrug having (R)-O-formylmandelamido and N-methylthiotetrazole side-groups.

Cefamandole nafate has a formylated D-mandelic amide moiety at C-7. The formate ester is cleaved rapidly in the host to release the more active cefamandole. The esterification also apparently overcomes the instability of cefamandole when it is stored in dry form. This agent has increased activity against Haemophil us influenzae and some Gram-negative bacilli as compared with the first-generation cephalosporins. Loss of the 5-thio-l-methyl-l-H-tetrazole moiety (referred to sometimes by the acronym MT T) from C-3 is associated with prothrombin deficiency and bleeding problems as well as with an Antabuse-like acute alcohol intolerance. On the other hand, this grouping enhances potency and prevents metabolism by deacetylation. Like the other second-generation cephalosporins, cefamandole is more active against Gram-negative bacteria. The principle clinical use is for lower respiratory tract, skin and skin structures, and bone and joint infections as well as septicemia and urinary tract infections when the organisms are sensitive.

The D-mandeloyl moiety of Cemandil sodium salt appears toconfer resistance to a few β-lactamases, since some β-lactamase–producing, Gram-negative bacteria (particularlyEnterobacteriaceae) that show resistance to cefazolin andother first-generation cephalosporins are sensitive tocefamandole. Additionally, it is active against some ampicillin-resistant strains of Neisseria and Haemophilus spp.Although resistance to β-lactamases may be a factor in determiningthe sensitivity of individual bacterial strains tocefamandole, an early study indicated that other factors,such as permeability and intrinsic activity, are frequentlymore important. The L-mandeloyl isomer is significantlyless active than the D-isomer.