651-06-9 Usage
Description
Sulfameter, also known as a sulfonamide antibiotic, is a compound characterized by a pyrimidine structure with a methoxy substituent at the 5-position and a 4-aminobenzenesulfonamido group at the 2-position. It is a crystalline solid that possesses potent antibacterial properties, making it a valuable asset in the medical field.
Uses
Used in Pharmaceutical Industry:
Sulfameter is used as an antibacterial agent for the treatment of various bacterial infections. Its primary applications include its use as a leprostatic agent to combat leprosy and as a therapeutic option for urinary tract infections. The antibiotic nature of Sulfameter makes it a crucial component in the development and formulation of medications targeting bacterial pathogens.
Additionally, Sulfameter has been investigated for its potential use in treating chloroquine-resistant malaria during pregnancy, showcasing its versatility and importance in addressing various medical challenges.
Originator
Sulla,Robins,US,1968
Manufacturing Process
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.
Therapeutic Function
Antibacterial
Pharmaceutical Applications
2-Sulfanilamido-5-methoxypyrimidine. A long-acting compound
with activity similar to that of sulfadiazine. Binding to
plasma proteins is about 75%.
Biochem/physiol Actions
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.
Check Digit Verification of cas no
The CAS Registry Mumber 651-06-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,5 and 1 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 651-06:
(5*6)+(4*5)+(3*1)+(2*0)+(1*6)=59
59 % 10 = 9
So 651-06-9 is a valid CAS Registry Number.
InChI:InChI=1/C11H12N4O3S/c1-18-9-6-13-11(14-7-9)15-19(16,17)10-4-2-8(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)