Chemical Properties
White Solid
Originator
Madribon,Roche,US,1958
Definition
ChEBI: A sulfonamide consisting of pyrimidine having methoxy substituents at the 2- and 6-positions and a 4-aminobenzenesulfonamido group at the 4-position.
Manufacturing Process
1.4 g of 4-phenylsulfonyl-2,6-dimethoxypyrimidine and 4 g of sodium
sulfanilamide (both dried over potassium hydroxide) were very finely ground
and heated in an oil bath for 10 hours at 120°C (inside temperature). The
reaction mixture was taken up in 30 ml of water and treated with 3 ml of 2 N
sodium hydroxide solution. After standing for one hour at 0°C, the turbid
solution was filtered and the filtrate was made alkaline with sodium carbonate.
After again standing for one hour at 0°C, the precipitate was filtered off (1.9 g
of regenerated sulfanilamide) and the filtrate was neutralized with acetic acid,
whereupon crystallization resulted. The isolated crystals of 4-sulfanilamido-
2,6-dimethoxypyrimidine weighed 1.3 g (84% of theory), melting point 190°C
to 196°C.
Therapeutic Function
Antibacterial
Pharmaceutical Applications
2,4-Dimethoxy-6-sulfanilamido-1,3-diazine. A rapidly absorbed
compound with a long half-life (38–40 h) and a high degree of
protein binding (98%). Renal clearance is very slow, and daily
dosage maintains adequate plasma levels.
Veterinary Drugs and Treatments
Sulfadimethoxine injection and tablets are approved for use in dogs
and cats for respiratory, genitourinary, enteric and soft tissue infections
caused by susceptible organisms. Sulfadimethoxine is used in
the treatment of coccidiosis in dogs although not approved for this
indication.
In horses, sulfadimethoxine injection is approved for the treatment
of respiratory infections caused by Streptococcus equi.
In cattle, the drug is approved for treating shipping fever complex,
calf diphtheria, bacterial pneumonia and foot rot caused by
susceptible organisms.
In poultry, sulfadimethoxine is added to drinking water to treat
coccidiosis, fowl cholera, and infectious coryza.
