Uses
Carbadox has been used to suppress aldosterone production, to study the spread of shiga toxin-producing Escherichia coli (STEC) strains, and to compare different antimicrobial activities. Carbadox is a quinoxaline-di-N-oxide antibiotic that is generally used in feed to swine to prevent dysentery and improve feed efficiency. It inhibits bacteria by intercalation and induction of mutations in bacterial genome.
Manufacturing Process
A solution of methylcarbazate (48.0 mg) in methanol (250 ml) is added all at
once at room temperature to a well stirred solution of 2-formylquinoxaline-
1,4-dioxide (100 g) in methanol (2.5 liters). Two drops of concentrated
hydrochloric acid are added. The mixture is stirred for 3 hours then filtered to remove the yellow crystalline product. The crystals of (2-
quinoxalinylmethylene)hydrazinecarboxylic acid methyl ester are washed with
methanol then air dried; M.P. 234.5-236°C (dec.). Yield=121.8 g. The product
is purified by refluxing in chloroform for 2 hours, followed by filtration and air
drying; M.P. 239.5-240°C (dec.).
The ultraviolet absorption spectrum (water) exhibits maxima at 236, 251,
303, 366 and 373 nm with extinction coefficients of 11,000, 10,900, 36,400,
16,100 and 16,200, respectively.
