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Sulfadiazine

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Sulfadiazine Chemical Properties
mp 253 °C (dec.)(lit.)
storage temp. 0-6°C
Merck 14,8903
CAS DataBase Reference68-35-9(CAS DataBase Reference)
NIST Chemistry ReferenceSulfadiazine(68-35-9)
EPA Substance Registry SystemBenzenesulfonamide, 4-amino-N-2-pyrimidinyl-(68-35-9)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38-42/43
Safety Statements 26-36
RIDADR 3249
WGK Germany 3
RTECS WP1925000
10
HazardClass 6.1(b)
PackingGroup III
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Sulfadiazine Usage And Synthesis
Sulfa drugsSulfadiazine is kind of commonly used sulfa-class anti-infection clinical drug in China. The molecular structure of sulfadiazine is similar as that of the amino benzoic acid (PABA), and can compete with PABA for acting on the dihydrofolate synthetase inside bacterial cells, thereby preventing the biosynthesis of folic acid (essential for bacteria) using PABA as the raw material and further reducing the amount of metabolically active folate, which is a indispensible material for bacterial synthesis of purines, thymidine and deoxyribonucleic acid (DNA) and thereby inhibiting the growth and reproduction of bacteria. Sulfadiazine hemolytic has inhibitory effect on various kinds of microorganisms including streptococcus, staphylococcus, meningococcus, pneumococcus, Neisseria gonorrhoeae, Escherichia coli, Shigella and other sensitive bacteria as well as Chlamydia trachomatis, actinomycetes, Plasmodium, Toxoplasma gondii and Star Nocardia. The advantages of sulfadiazine include the high effective blood concentration, low serum protein binding rate, and easy penetration into the cerebrospinal fluid. It is the first-choice of drug for the treatment of epidemic meningitis. However, in recent years, drug resistant strains of meningococcal against sulfadiazine have increased (20% according to domestic reports and 33% according to foreign reports of drugs resistant strains). For strain being resistant to the chemicals, we can apply penicillin treatment to kill them. The disadvantage of sulfadiazine is that it is more prone to get crystal precipitation in the urinary tract and therefore should be combined with sodium bicarbonate. Recent studies have showed that the half-life of it is 17 hours and thus belong to moderate-efficacy sulfa drugs with administration twice daily being enough. However, it is generally still use as a short-term type. It is clinically often applying sulfadiazine for treatment of epidemic cerebrospinal meningitis, upper respiratory tract infection, meningococcal meningitis, otitis media, carbuncle boils, puerperal fever, plague, local or systemic soft tissue infections, urinary tract infections and acute dysentery; it can still be used for the treatment of respiratory tract infections, intestinal infections, and typhoid.
Chemical PropertiesIt is White or white-like crystal or powder and is odorless and tasteless. It gradually becomes dark upon exposure to light. It is insoluble in water, soluble in boiling water (1:60), slightly soluble in ethanol and acetone and insoluble in chloroform and ether. It is easily soluble in dilute hydrochloric acid, sodium hydroxide solution or ammonia solution. Its melting point is 252 ~ 256 ℃ (decomposition occurs at the same time). Its sodium salt is a white crystalline powder and is odorless with slightly bitter taste. Its sodium salt gradually turns to brown color up exposure to light. When being subject to long-term storage in the moist air, it can slowly absorb carbon dioxide and precipitate out sulfadiazine. It is soluble in water, slightly soluble in ethanol, but insoluble in chloroform and ether. Its 10% aqueous solution has a pH of 9.5 to 10.5.
Silver sulfadiazineSulfadiazine silver is the silver salt of sulfadiazine. It is a topical sulfa drug for treating burn wound. It is white or white-like crystalline powder and is odorless with slightly bitter taste. It is perishable upon being exposed to light or heat. It is insoluble in water, ethanol, ether and chloroform. Its melting point is 252 ~ 258 ℃. It has the antibacterial effect of sulfadiazine as well as the convergence effect of silver. Upon taking effect, it releases silver ion and sulfadiazine with the former one binding to the DNA and RNA which further affects the formation of bacterial cell wall and leads to bacterial death while the latter one can inhibit the bacterial growth by preventing bacterial folate metabolism. It has a strong anti-bacterial effect on Pseudomonas aeruginosa with the effect being stronger than Mafenide while being without the disadvantage of easily causing acidosis of the Mafenide. It can be used for the prevention and control of P. aeruginosa and E. coli infection on the wound surface, especially suitable for preventing the infection of burn and scald wound. It can make the wound surface be dry, scab and promote early healing. It has a good efficacy in prevention of infection after burning; however, it has a poor efficacy on the existing infection.
Since 1967 when FOX began use it as a topical antibiotic, although drug resistant strains had reported or allergic reactions such as hemolysis, drug rash and neutropenia may also occur, it is still by far the most widely used type drug for external use with the best efficacy. Commonly used dosage includes 1% cream and 20% suspension. Upon using, you should change dressing once a day in which you should clean the old drug and re-coated new drug to ensure the efficacy. Silver sulfadizine is made from the reaction between sodium sulfadiazine and silver nitrate.
The above information is edited by the chemicalbook of Dai Xiongfeng.
Sodium sulfadiazineSulfadiazine sodium is the sodium salt sulfadiazine, briefly called SD-Na. It is white crystalline powder and is odorless with slightly bitter taste. Its color gradually changes upon exposure to daylight. Long-term placement in humid air causes the gradual absorption of carbon dioxide and the precipitation of sulfa. It is made through the reaction between sulfadiazine and sodium hydroxide. It can be used for the treatment of the infection caused by hemolytic streptococcus, pneumococcus, and meningococcus.
Pharmacological effectsSulfadiazine hemolytic has inhibitory effect on various kinds of microorganisms including streptococcus, staphylococcus, meningococcus, pneumococcus, Neisseria gonorrhoeae, Escherichia coli, Shigella and other sensitive bacteria as well as Chlamydia trachomatis, actinomycetes, Plasmodium, Toxoplasma gondii and Star Nocardia. The antibacterial activity of this product is similar as that of sulfasuccinamide. But in recent years, there are increased reports regarding the bacterial resistance to this product, especially in Streptococcus, Neisseria and Enterobacteriaceae. Sulfa-class belongs to broad-spectrum antibacterial agents. The molecular structure of sulfadiazine is similar as that of the amino benzoic acid (PABA), and can compete with PABA for acting on the dihydrofolate synthetase inside bacterial cells, thereby preventing the biosynthesis of folic acid (essential for bacteria) using PABA as the raw material and further reducing the amount of metabolically active folate, which is a indispensible material for bacterial synthesis of purines, thymidine and deoxyribonucleic acid (DNA) and thereby inhibiting the growth and reproduction of bacteria.
PharmacokineticsThis product can be easily absorbed after oral administration (more than 70% of the administrated drug can be absorbed), but with the absorption rate being relative slow. After a single oral dose of 2g, the plasma concentration reaches peak after 3 ~ 6 hours with the peak of free plasma concentration being about 30 ~ 60μg / ml. After drug absorption, it widely distributed in body tissue and pleural fluid, peritoneal fluid, synovial fluid, aqueous humor, saliva, sweat, urine and bile. The drug is easy to penetrate through the blood - brain barrier as well as being able to enter into the breast milk and penetrate through the placental barrier. When there is no meningeal inflammation, cerebrospinal fluid drug concentration is about 50% of the plasma concentration. While the value can be 50% to 80% when there is meningeal inflammation.
The drug has a low plasma protein binding rate which is around 38% to 48%. The elimination life for patients of normal renal function is about 10 hours while it can be as long as 34 hours for patients with kidney failure. Sulfadiazine drug is mainly deactivated in the liver through acetylation metabolism, followed by deactivation upon binding to the glucuronide in the liver. The drug is primarily excreted through glomerular filtration. Within 48 to 72 hours after administration of the drug, around 60% to 85% of administrated drug is excreted form urine. In addition, there is still a small amount of drugs being able to be discharged through feces, milk, and bile. Hemodialysis can partially clear the drug. However, peritoneal dialysis can’t effectively remove the drugs.
IndicationsSulfa drugs belong to broad-spectrum antibiotic. However, because of the resistance of many current clinical common pathogens to this class of drugs, it is only used for treating the infection caused by sensitive bacteria and other kinds of susceptible pathogens.
Sulfadiazine (not including the FDC of this drug together with trimethoprim) has its main indications as follows:
1. Used for prevention and treating the meningococcal meningitis caused by sensitive Meningococcal.
2. When being used in combination with trimethoprim, it can be used for treating the otitis media and other kinds of soft tissue infection caused sensitive Haemophilus influenzae, Streptococcus pneumoniae and other kinds of Streptococcus.
3. Used for treating disease related to star nocardia.
4. Used as the adjuvant drug assisting in the treatment of chloroquine-resistant falciparum malaria.
5. Used as the secondary-choice drug for treatment of Chlamydia trachomatis-induced urethritis and cervicitis.
6. Used as the secondary-choice drug for treatment of neonatal inclusion conjunctivitis caused by Chlamydia trachomatis.
Adverse reactions1. it can cause kidney damage. This product has a low acetylation ratio. This product and its acetylated compound has a low solubility in the urine and is easily subject to crystal precipitation upon a acidic urine, doing harm to the renal tubular as well as the epithelial cells of other urinary tract and causing crystallization of urine, hematuria, proteinuria, and even urine retention or uremia in severe cases.
2. hematopoietic system reactions include neutropenia, acute hemolytic anemia, aplastic anemia, and thrombocytopenia purpura.
3. gastrointestinal reactions include nausea and vomiting. Occasionally: jaundice, liver and spleen. For newborns, premature children, it can cause jaundice, and even kernicterus.
4. urinary system damage: As the prototype of sulfonamides and acesulfame are primarily subject to renal excretion and thus have higher concentrations in the urine. Upon acidic urine, its solubility decreases and can be crystallized and precipitated in renal tubules, renal pelvis, ureter or bladder, causing crystallization of urine, hematuria, proteinuria, dysuria, oliguria and even urine retention.
5. allergic reactions: commonly include rash, drug fever and even exfoliative dermatitis, erythema multiforme exudativum in severe cases. This often occurs during the 7 to 10 days after the medication. Photosensitive dermatitis has also been reported.
Production method1. Propargyl alcohol Method: take acetylene and formaldehyde to subject to catalytic acetylenation (Copper acetylide as the catalyst) in a pressurized (1.96 ~ 2.3MPa) to obtain propargyl alcohol, which is further subject to catalytic oxidation (2.36MPa) to obtain acraldehyde, which simultaneously has addition reaction together with diethylamine to generate diethylamino acrolein. Further go through condensation reaction with sulfa guanidine, acid precipitation, refining to obtain the finished product of sulfadiazine.
Reaction formula
2. vinyl ether method: through the addition reaction between acetylene and ethanol vapor under the catalysis of potassium hydroxide-calcium oxide which produces vinyl ether, which further has condensation reaction with dimethylformamide in the presence of phosphorus trichloride; further go through cyclization reaction with sulfaguanidine in the presence of sodium methoxide, then perform acid precipitation to get the finished product of sulfadiazine.
Reaction formula
ApplicationIt is excellent kinds of sulfa drugs with strong antibacterial activity, good efficacy, rapid absorption, slow excretion rate and high plasma concentration. It is clinically used for treating upper respiratory tract infection, Meningococcal meningitis, otitis media, boils carbuncle, puerperal fever, urinary tract infections and acute dysentery and so on.
It is a sulfa-type drug which is used for the treatment of infection caused by hemolytic streptococcus, pneumococcus, meningococcis, Neisseria gonorrhea, and E. coli.
It is a sulfa drug with antibacterial effect and convergence effect.
Chemical PropertiesWhite to slightly yellow crystalline pow
UsageAntibacterial.
UsageDMSO soluble potent immunosuppressant, neuroprotective neuroregenerative, in vitro T cell proliferation blocker. disrupts calcineurin-mediated signal transduction in T lymphocytes
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