Nalidixic acid has a bactericidal or bacteriostaic effect depending on the sensitivity of the microorganism and the concentration. It is effective with respect to Gram-negative microorganisms, such as colon bacillus, salmonella, shigella, proteus, and Fridlender's bacillus. It is used for pyeolonephritis, cystitis, urethritis, prostatitis, and gastrointestinal tract infections. Synonyms of this drug are negram, nevigramon, uralgin, urogram, vintron, and many others.
Oxolinic acid: Oxolinic acid, 5-ethyl-5,8-dihydro-8-oxo-1-dioxolo[4,5-g]-quinolin-7-carboxylic acid (33.2.9), is basically synthesized by the same synthetic scheme as nalidixic acid, although it uses 3,4-methylendioxyanyline (33.2.6) as the starting aromatic amine component, and not the 2-amino-6-methylpyridine used to make nalidixic acid. This compound is obtained by hydrogenation to 3,4-methylendioxy-1-nitrobenzene (33.2.5), which is in turn synthesized by nitrating 1,2-methylendioxybenzene with nitric acid. The resulting 3,4-methylendioxyaniline (33.2.6) is then reacted with ethoxymethylenmalonic ester to make the substitution product (33.2.7), which when heated cyclizes to ethyl ester of 4-hydroxy-6,7-methylendioxyquinolin-3-carboxylic acid (33.2.8). Hydrolyzis of this with a base in dimethylformamide and direct treating of the obtained product with ethyl iodide gives the desired oxolinic acid [65-67].
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