ChemicalBook > Product Catalog > API > Synthetic Anti-infective Drugs > Sulfonamides and synergist > Sulfamethazine
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)
Sulfamethazine Usage And Synthesis
- Brand Name(s) in USBrand Name(s) in US
- Chemical PropertiesWhite to Off-Solid
- 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
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.
- 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.
- Chemical 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 Preparation Products And Raw materials
- SULFAMETHAZINE SULFADIMIDINE-D4 N-Acetyl Sulfamethazine-d4 SULFAMETHAZINE (SM2) SODIUM ANTI-SULFAMETHAZINE (AMINE LINK),ANTI-SULFAMETHAZINE AURORA 480 N-(4,6-DIMETHYL-2-PYRIMIDINYL)-4-NITROBENZENESULFONAMIDE SULFABROMOMETHAZINE (PHENYL-13C6) SULFAMETHAZINE (PHENYL-13C6) sulfamethazine-n4-acetyl N-[4-(4,6-DIMETHYL-PYRIMIDIN-2-YLSULFAMOYL)-PHENYL]-PHTHALAMIC ACID Sulfadimethoxine sodium salt SULFAMETHAZINE SODIUM SALT Dimethyl sebacate Dacthal CHLORODIMETHYLVINYLSILANE 3-Aminobenzenesulfonamide Sulfamerazine
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