Sulfamethazine

Sulfamethazine Basic information
Brand Name(s) in US
Product Name:Sulfamethazine
Synonyms:(p-Aminobenzolsulfonyl)-2-amino-4,6-dimethylpyrimidin;2-(4-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine;6-(4’-aminobenzol-sulfonamido)-2,4-dimethylpyrimidin;6-(4'-Aminobenzol-sulfonamido)-2,4-dimethylpyrimidin;A-502;Azolmetazin;Benzenesulfonamide, 4-amino-N-(4,6-dimethyl-2-pyrimidinyl)-;benzenesulfonamide,4-amino-N-(4,6-dimethyl-2-pyrimiidinyl)-
CAS:57-68-1
MF:C12H14N4O2S
MW:278.33
EINECS:200-346-4
Product Categories:Active Pharmaceutical Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Antibiotics for Research and Experimental Use;Biochemistry;Sulfonamides (Antibiotics for Research and Experimental Use);Pharmaceutical intermediate;Animal medication;SULFASURE;57-68-1
Mol File:57-68-1.mol
Sulfamethazine Structure
Sulfamethazine Chemical Properties
Melting point 197 °C
Boiling point 294°C (rough estimate)
density 1.2997 (rough estimate)
refractive index 1.6440 (estimate)
storage temp. 2-8°C
solubility acetone: soluble50mg/mL
form Crystalline Powder
pka7.4, 2.65(at 25℃)
color white to off-white
Water Solubility 150mg/100mL (29 ºC)
Merck 14,8905
BRN 261304
Stability:Stable, but light sensitive. Incompatible with strong oxidizing agents.
CAS DataBase Reference57-68-1(CAS DataBase Reference)
NIST Chemistry ReferenceSulfamethazine(57-68-1)
IARC3 (Vol. 79) 2001
EPA Substance Registry SystemSulfamethazine (57-68-1)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 23-24/25-36-26
WGK Germany 2
RTECS WO9275000
10
TSCA Yes
HS Code 29350090
Hazardous Substances Data57-68-1(Hazardous Substances Data)
ToxicityLD50 i.p. in mice: 1.06 g/kg (Bobranski)
MSDS Information
ProviderLanguage
2-(p-Aminobenzenesulfonamido)-4,6-dimethylpyrimidine English
SigmaAldrich English
ACROS English
ALFA English
Sulfamethazine Usage And Synthesis
Brand Name(s) in USBrand Name(s) in US
DescriptionSulfamethazine is an antibacterial sulfonamide. Like other sulfonamides, sulfamethazine is bacteriostatic, competitively inhibiting dihydropteroate synthase to block folate synthesis and inhibit growth and multiplication. Sulfamethazine is metabolized by cytochrome P450 isoforms and arylamine N-acetyltransferase 2 in a sex-dependent manner.
Chemical PropertiesWhite to Off-Solid
OriginatorCremomethazine,MSD,US,1947
UsesSulfamethazine is an antibacterial.This compound is a contaminant of emerging concern (CECs).
DefinitionChEBI: A sulfonamide consisting of pyrimidine with methyl substituents at the 4- and 6-positions and a 4-aminobenzenesulfonamido group at the 2-position.
Manufacturing ProcessA flask heated in an oil bath is filled with 600 ml water and 60 g (1 mol) glacial acetic acid (or an equivalent quantity of diluted acetic acid). While stirring 235 g (1.1 mols) anhydrous p-aminobenzenesulfonamidoguanidine (or an equivalent quantity of a nonanhydrous product) and 122 g (1 mol) sodium acetylacetonate 100% purity (or an equivalent quantity of product of a lower purity) are introduced into the flask while stirring.
The temperature of the reaction mixture is brought to 102°C to 103°C, the mixture is further stirred at this temperature during 24 hours. The pH value of the mixture, which should range between 5 and 6 is checked during the reaction.
On expiry of the reaction period heating is cut off, the mass being cooled or allowed to cool down to 60°C.
Filtering under suction is effected, the solids on the filter being washed with 100 ml water at 80°C.
After drying of the product on the filter 256 g of 2-paminobenzenesulfonamido- 4,6-dimethylpyrimidine, melting point 196°C to 197°C, purity 99.5% are obtained. The output is 92% of the theory calculated with respect to the sodium acetylacetonate employed.



Brand nameCalfspan Tablets [Veterinary] (Fort Dodge Animal Health); Sulka S Boluses [Veterinary] (Fort Dodge Animal Health); SulfaSURE SR Bolus [Veterinary] (Boehringer Ingelheim Animal Health);Crermomethazine;Deladine;Dimezathine;Hava-span;Intradin;Neotrizine;Rigesol;Rivodin;S-dimidine;Spanbolet;Sulka-s;Sulphamezathine;Sulphfmezatine;Superseptyl;Sustain iii;Tersulpha;Trisulfaminic;Trisulfaminie.
Therapeutic FunctionAntimicrobial
World Health Organization (WHO)Sulfadimidine, a sulfonamide anti-infective agent, was introduced in 1942 for the treatment of bacterial infections. The importance of sulfonamides has subsequently decreased as a result of increasing resistance and their replacement by antibiotics which are generally more active and less toxic. The sulfonamides are known to cause serious adverse effects such as renal toxicity, sometimes fatal exfoliative dermatitis and erythema multiforma and dangerous adverse reactions affecting blood formation such as agranulocytosis and haemolytic or aplastic anaemia. Sulfadimidine is still used in some countries as a injectable or oral antimicrobial for susceptible infections.
Antimicrobial activityThis drug is used for pneumococcal, staphylococcal, and streptococcal infections as well as for sepsis, gonorrhea, and other infectious diseases. Synonyms of this drug are sulfadiamezin and sulfadimidin.
General DescriptionSulfamethazine’splasma half-life is 7 hours. This compound is similar inchemical properties to sulfamerazine and sulfadiazine butdoes have greater water solubility than either. Its pKa is 7.2.Because it is more soluble in acid urine than sulfamerazineis, the possibility of kidney damage from use of the drug isdecreased. The human body appears to handle the drugunpredictably; hence, there is some disfavor to its use in thiscountry except in combination sulfa therapy (in trisulfapyrimidines,USP) and in veterinary medicine.
General DescriptionOdorless sticky, white or creamy-white crystalline powder. Slightly bitter taste. An antibacterial.
Air & Water ReactionsWater solubility increases rapidly with increasing pH [Merck]. Insoluble in water.
Reactivity ProfileSulfamethazine is sensitive to light and may also be sensitive to heat. The presence of oxygen and moisture may accelerate the effects of heat and light .
Fire HazardFlash point data for Sulfamethazine are not available; however, Sulfamethazine is probably combustible.
Pharmaceutical Applications2-Sulfanilamido-4,6-methylpyrimidine (syn: sulphamethazine, sulfamezathine). A water-soluble compound, unstable on exposure to light. It is usually administered by mouth and is a component of some triple sulfonamide combinations.
The spectrum is typical of the group, but sulfadimidine exhibits relatively low potency. It is well absorbed after oral administration. It is extensively metabolized, predominantly by acetylation. The mean plasma half-life (1.5–5 h) varies with acetylator status.
In addition to side effects common to the group, a serious interaction between ciclosporin (cyclosporin A) and sulfadimidine, leading to reduced ciclosporin levels, has been reported.

Biochem/physiol ActionsSulfamethazine is an antimicrobial sulfur drug that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfamethazine is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid. It induces CYP3A4 expression and is acetylated by N-acetyltransferase. It exhibits sex dependent pharmacokinetics, metabolized by the male specific isoform CYP2C11. Sulfamethazine is bacteriostatic.
Safety ProfileModerately toxic by intravenous and intraperitoneal routes. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental tumorigenic data. When heated to decomposition it emits very toxic fumes of SOx and NOx.
SynthesisSulfamethazine, N1 -(4,6-dimethyl-2-pyrimidinyl)sulfanilamide (33.1.13), is also synthesized in the aforementioned manner by reacting 4-acetylaminobenzenesulfonyl chloride with 2-amino-4,6-dimethylpyrimidine, which is in turn synthesized by condensing acetylacetone with guanidine followed by hydrolysis of the acetylamino group using a base.
Purification MethodsCrystallise it from dioxane or aqueous dioxane. [Caldwell et al. J Am Chem Soc 63 2188 1941, Roblin et al. J Am Chem Soc 64 567 1942, Beilstein 25 III/IV 2215.]
SULFAMETHAZINE EIA N-(4,6-DIMETHYL-2-PYRIMIDINYL)-4-NITROBENZENESULFONAMIDE Dacthal N-Acetyl Sulfamethazine-d4 AURORA 480 SULFABROMOMETHAZINE (PHENYL-13C6) SULFAMETHAZINE-N4-ACETYL N-[4-(4,6-DIMETHYL-PYRIMIDIN-2-YLSULFAMOYL)-PHENYL]-PHTHALAMIC ACID SULPHADIMIDINE SODIUM Sulfadimethoxine sodium salt Sulfamethazine-D4 SULFAMETHAZINE ANTI-SULFAMETHAZINE (AMINE LINK),ANTI-SULFAMETHAZINE SULFAMETHAZINE (SM2) SODIUM SULFAMETHAZINE (PHENYL-13C6) Dimethyl sebacate sulfamethazine-n4-acetyl SULFADIMIDINE-D4

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