ChemicalBook > Product Catalog > API > Synthetic Anti-infective Drugs > Sulfonamides and synergist > Sulfamerazine
Sulfamerazine Chemical Properties
- Melting point:234-238°C
- Boiling point:519.1±52.0 °C(Predicted)
- Density 1.3364 (rough estimate)
- refractive index 1.6440 (estimate)
- storage temp. 0-6°C
- pkapKa 2.29(H2O t = 24.0 I = 0.5 (NaCl)) (Uncertain)
- form neat
- Water Solubility 202mg/L(20 ºC)
- Merck 14,8913
- BRN 249133
- CAS DataBase Reference127-79-7(CAS DataBase Reference)
- NIST Chemistry ReferenceSulfamerazine(127-79-7)
- EPA Substance Registry SystemBenzenesulfonamide, 4-amino-N-(4-methyl-2-pyrimidinyl)- (127-79-7)
Sulfamerazine Usage And Synthesis
- Chemical PropertiesWhite Solid
- DefinitionChEBI: A sulfonamide consisting of pyrimidine with a methyl substituent at the 4-position and a 4-aminobenzenesulfonamido group at the 2-position.
- Manufacturing ProcessTo a well agitated solution of 6.95 grams of 2-amino-6-methyl pyrimidine in
40 cc of pyridine, 15 grams of p-acetylaminobenzenesulfonyl chloride are
added in small portions over a 30 minute period. The reaction mixture is then
heated on a steam bath for 30 minutes, the free pyridine being then removed
under reduced pressure and the residue mixed with cold water, and the latter
mixture is vigorously stirred. The solid reaction product is removed by
filtration and washed with cold water.
There is obtained a yield of 14 grams of crude 2-(pacetylaminobenzenesulfonamido)- 6-methyl pyrimidine, which on recrystallization from alcohol and water melts at 238° to 239°C. The crude product is hydrolyzed by suspending it in 400 cc of 2 N hydrochloric acid and warming until solution is complete. The solution is neutralized with sodium carbonate and the precipitated 2-(sulfanilamido)-6-methyl pyrimidine is removed by filtration. The latter on recrystallization from alcohol and water shows a melting point of 225° to 226°C.
- Therapeutic FunctionAntibacterial
- Antimicrobial activityLike all examined sulfanilamides, this drug is effective in treating infections caused by streptococci, gonococci, pneumococci, staphylococci, and also colon bacillus. Synonyms of this drug are dosulfin, polagin, romezin, and others.
- Pharmaceutical Applications2-Sulfonamido-4-methylpyrimidine. A component of some triple sulfa combinations. Plasma half-life is c. 24 h and protein binding c. 75%. It is less active than sulfadiazine.
- Safety ProfileModerately toxic by intravenous and subcutaneous routes. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of NO, and SOx,.
- Chemical SynthesisSulfamerazine, N1
-(4-methyl-2-pyrimidinyl)sulfanilamide (33.1.12), is
also synthesized in the manner described above, which is by reacting 4-acetylaminobenzenesulfonyl chloride with 2-amino-4-methylpyrimidine (33.1.10), which is in turn synthesized by the traditional scheme of synthesizing derivatives of pyrimidine. Acetoacetic
ester is condensed with guanidine to give 4-methyl-2-aminopyrimidin-6-one (33.1.8).
Reacting this with phosphorous oxychloride gives 4-methyl-2-amino-6-chloropyrimidine
(33.1.9). The chlorine atom at C6 of the pyrimidine ring is then removed by reduction with
hydrogen using a palladium on carbon catalyst. The resulting 4-methyl-2-aminopyrimidine (33.1.10) is then reacted with 4-acetylaminobenzenesulfonyl chloride to make an
acetanilide derivative (33.1.11), the subsequent hydrolysis of which with base leads to the
formation of the desired sulfamerazine.
- METSULFURON METHYL 2,2-DIMETHYL-5-(((4-(((4-METHYLPYRIMIDIN-2-YL)AMINO)SULFONYL)PHENYL)AMINO)METHYLENE)-1,3-DIOXANE-4,6-DIONE Silver sulfadiazine Thiophanate-methyl Parathion-methyl Sulfamerazine SULPHADIMIDINE SODIUM Tribenuron methyl Sulfadimethoxine Pirimiphos-methyl SULFAMERAZINE SODIUM(SM1-NA)(NDC:56631-1715),SODIUM SULFAMERAZINE,sulfamerazine sodium,SULFAMERAZINE, SODIUM SALT MONOHYDRATE,SULFAMERAZINE SODIUM SALT Sulfamethazine Sulfadiazine Sulfameter Methyl salicylate Methyl Kresoxim-methyl Methyl acetate
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