Sulfameter is an antibacterial.
Sulfameter is a sulfonamide antibiotic used as a leprostatic agent and to treat urinary tract infections. It has been investigated as a potential therapy for chloroquine-resistant malaria during pregnancy.
ChEBI: A sulfonamide consisting of pyrimidine having a methoxy substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 2-position.
2-Amino-5-methoxy pyrimidine is obtained having a melting point of about
300°C by condensation of methoxymalonic acid ester with guanidine
carbonate in the presence of sodium ethylate. The resultant reaction product
is then converted to 2-amino-5-methoxy-4,6-dichloropyrimidine (melting point
216°C to 217°C) by heating this reaction product with phosphorus
oxychloride. The dichloro compound is then suspended in water with zinc dust
and is tested in the presence of caustic alkaline or carbonates to produce the
2-aminod-methoxy pyrimidine compound, melting point 80°C to 82°C,
(benzene).
12.6 g of 2-amino-5-methoxy pyrimidine, 26.4 g of carbethoxy-sulfanilic acid
chloride and 50 cc of dry pyridine are heated for 30 minutes with frequent
shaking to a temperature of 80°C. The reaction product is then mixed with 200
cc of water and with dilute hydrochloric acid (0.1 N) until the reaction is acid to
Congo Red indicator. A precipitate is formed which is then filtered under
suction, washed with distilled water, and dried at 150°C. A practically
quantitative yield is recovered of 2-(p-carbethoxyaminobenzene-sulfonamido)-
5-methoxypyrimidine, melting point 248°C to 250°C.To hydrolyze the sulfapyrimidine compound, the same is heated at 90°C with
200 cc of 2 N potassium hydroxide solution for about one hour until complete
solution is obtained. The resultant solution is then cooled to room temperature
(25°C) and acidified with acetic acid to precipitate the hydrolyzed product,
which is then recrystallized from dilute acetone admixed with animal charcoal.
Chemical structure: sulfonamide
Pharmaceutical Applications
2-Sulfanilamido-5-methoxypyrimidine. A long-acting compound
with activity similar to that of sulfadiazine. Binding to
plasma proteins is about 75%.
Sulfameter is a sulfonamide antibiotic. Sulfonamides block the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfonamides are competitive inhibitors of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid. Sulfameter is a dihydrofolate reductase (DHFR) inhibitor. Sulfonamides are active against Gram positive bacteria and Gram negative bacteria. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.
