Sulfadiazine
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Sulfadiazine
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CAS No:
68-35-9
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Formula:
C10H10N4O2S
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Chemical Name:
Sulfadiazine
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Synonyms:
Benzenesulfonamide,4-amino-N-2-pyrimidinyl-;Sulfanilamide,N1-2-pyrimidinyl-;Sulfanilamide,N1-2(1H)-pyrimidinylidene-;4-Amino-N-2-pyrimidinylbenzenesulfonamide;RP 2616;Adiazine;Coco-Diazine;Cremodiazine;Debenal;Diazin;Di-Azo-Mul;Diazyl;Eskadiazine;Honey diazine;Lipo-Diazine;Lipo-Levazine;Microsulfon;Neazine;Pyrimal;N1-2-Pyrimidylsulfanilamide;SDA;Spofadrizine;Sterazine;Sulfadiazine;2-Sulfanilamidopyrimidine;2-Sulfanilylaminopyrimidine;Sulfazine;Sulphadiazine;Sulfapyrimidine;Theradiazine;A 306;Sulfazin (Russian pharmaceutical);Sulfazin;Sulfadiazin;Adiazin;Pirimal;Sulfapirimidin;N1-2-Pyrimidinylsulfanilamide;Liquadiazine;Sanodiazine;SN 112;Deltazina;Piridisir;Diazolone;Diazovit;2-(4-Aminobenzenesulfonamido)pyrimidine;Sulphadiazine E;Sulfadiazina Reig Jofre;Sulfolex;NSC 35600;2-(4-Aminobenzenesulfonylamino)pyrimidine;4-Amino-N-(2-pyrimidyl)benzenesulfonamide;2-(p-Aminobenzenesulfonamido)pyrimidin;4-[[(Pyrimidin-2-yl)amino]sulfonyl]aniline;141582-64-1
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CAS No:
Description
Sulfadiazine is a sulfonamide antibiotic.Target: AntibacterialSulfadiazine eliminates bacteria that cause infections by stopping the production of folate inside the bacterial cell, and is commonly used to treat urinary tract infections (UTIs). In combination, sulfadiazine and pyrimethamine, can be used to treat toxoplasmosis, a disease caused by Toxoplasma gondii. From Wikipedia.The ulcers who treated with silver sulfadiazine cream responded rapidly, with one-third showing bacterial leve
Solid
Sulfadiazine is a sulfonamide consisting of pyrimidine with a 4-aminobenzenesulfonamido group at the 2-position. It has a role as an antimicrobial agent, an antiinfective agent, a coccidiostat, an antiprotozoal drug, an EC 2.5.1.15 (dihydropteroate synthase) inhibitor, an EC 1.1.1.153 [sepiapterin reductase (L-erythro-7,8-dihydrobiopterin forming)] inhibitor, a xenobiotic, an environmental contaminant and a drug allergen. It is a member of pyrimidines, a sulfonamide, a substituted aniline and a sulfonamide antibiotic. It derives from a sulfanilamide. It is a conjugate acid of a sulfadiazinate.|One of the short-acting sulfonamides used in combination with pyrimethamine to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections.|Sulfadiazine is a Sulfonamide Antibacterial.|Sulfadiazine is a sulfonamide antibacterial agent used in the therapy of mild-to-moderate infections due to sensitive organisms. Sulfadiazine, like other sulfonamides, is a well known cause of clinically apparent, idiosyncratic liver injury.|Sulfadiazine is a synthetic pyrimidinyl sulfonamide derivative, short-acting bacteriostatic Sulfadiazine inhibits bacterial folic acid synthesis by competing with para amino benzoic acid. It is used in combination with pyrimethamine to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections. (NCI04)|One of the short-acting SULFONAMIDES used in combination with PYRIMETHAMINE to treat toxoplasmosis in patients with acquired immunodeficiency syndrome and in newborns with congenital infections.
Sulfadiazine Basic Attributes
250.27700
250.28
200-685-8
0N7609K889
757324|35600
DTXSID7044130
C29468
J01EC02|D - Dermatologicals|J - Antiinfectives for systemic use
2935009090
Characteristics
106.35000
-0.1
Solid
1.52 g/cm3
255.5 °C (decomp)
512.6ºC at 760 mmHg
263.8ºC
1.679
67.13mg/L(25 ºC)
0-6ºC
LD50 oral in mouse: 1500mg/kg
6.36None
6.36
150.9 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|148.7 Ų [M+H]+ [CCS Type: TW]|153.9 Ų [M+H]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|163 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with Waters Major Mix]|155.43 Ų [M-H]-
Safety Information
III
6.1(b)
UN 3249
3
R22
26-36
WP1925000
Xn; Xi
P261-P280-P284-P304 + P340-P305 + P351 + P338-P342 + P311
H302-H315-H317-H319-H334-H335
|Danger|H302 (99.4%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P273, P280, P285, P301+P312, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 170 companies from 21 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
Oral LD50 in mouse is 1500 mg/kg.
Sulfadiazine, like other sulfonamides, causes a characteristic idiosyncratic liver injury which has features of drug-allergy or hypersensitivity. The typical onset is sudden development of fever and rash followed by jaundice within a few days or weeks of starting the medication. The pattern of injury is typically mixed, although fatal cases are often hepatocellular and prolonged cholestatic cases have also been described. Eosinophilia or atypical lymphocytosis are also common and the clinical pattern can be considered a part of DRESS syndrome (drug rash with eosinophilia and systemic symptoms). Cases of Stevens Johnson syndrome due to sulfadiazine have also been described. Sulfonamides such as sulfadiazine have been linked to many cases of acute liver failure and as a class, the sulfonamides still rank in the top 5 to 10 causes of drug induced, idiosyncratic fulminant hepatic failure. However, most cases of sulfonamide induced liver injury resolve rapidly, usually within 2 to 4 weeks unless cholestasis is severe. Onset of injury is more rapid with rechallenge and can appear within a day or reexposure. Patients with hepatic injury due to sulfadiazine may have a history of previous exposure to the drug without injury. Sulfonamides such as sulfadiazine can also cause mild and transient ALT elevations that do not progress to jaundice or more severe liver injury either alone or as a part of a generalized hypersensitivity reaction. Sulfonamides have also been linked to hepatic granulomas.
Drug Information
For the treatment of rheumatic fever and meningococcal meningitis
Sulfadiazine is a sulfonamide antibacterial agent used in the therapy of mild-to-moderate infections due to sensitive organisms. Sulfadiazine, like other sulfonamides, is a well known cause of clinically apparent, idiosyncratic liver injury.
Antiinfective Agents
Sulfadiazine has known transformation products that include N4-Acetylsulfadiazine.
Sulfadiazine is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.
Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)|Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Agents useful in the treatment or prevention of COCCIDIOSIS in man or animals. (See all compounds classified as Coccidiostats.)
Sulfadiazine is excreted largely in the urine.
Sulfadiazine has known human metabolites that include Sulfadiazine hydroxylamine.
Sulfadiazine is a competitive inhibitor of the bacterial enzyme dihydropteroate synthetase. This enzyme is needed for the proper processing of para-aminobenzoic acid (PABA) which is essential for folic acid synthesis. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Sulfadiazine
Sulfadiazine Use and Manufacturing
A mixing 8.6 g NH4Cl and 23. lg (NH4) 2C03 in a certain ratio, Adding activated carbon catalyst, Then add 32g of dicyandiamide heated to melt at 150 ° C for 30min; B To join the above Rong melt liquid 80g p-aminosulfonamide, 70g sodium carbonate continue to melt financial, in 25min heated to 150 ° C, to maintain 30min; C To the mixture obtained in step B, 400 ml of boiling water was added and the mixture was stirred well. The resulting suspension was cooled to 40 ° C and filtered to obtain crude sulfanilamide. To the flask, 93 g of a 25percent methanol solution of sodium methoxide, 33 g of crude sulfanilamide, Stirring to join malondialdehyde 13. 5g, heating to 65 ° C, reaction 2h, Complete ring condensation reaction, recovery of methanol after sulfadiazine crude. Add 200ml of water to the crude, heating, saturated with hydrogen peroxide to adjust the pH to 9. 5, after the whole solution, add 20g of activated carbon, heat decolorization at 80 ° C. Filtration, the filtrate added ‰ 5g ammonium chloride, with 10percent acetic acid to adjust the pH to 5.2. Precipitation crystal, cold after filtration, washing, drying Of the sulfadiazine quality, yield 89percent, purity of 98.0percent.
Antibacterial.
Benzenesulfonamide, 4-amino-N-2-pyrimidinyl-: ACTIVE
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals -> Animal Drugs -> Approved in Taiwan|Pharmaceuticals -> Antiinfectives for systemic use -> Antibacterials for systemic use -> Sulfonamides and trimethoprims -> Intermediate-acting sulfonamides -> Antibiotics
Computed Properties
Molecular Weight:250.28
XLogP3:-0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:250.05244675
Monoisotopic Mass:250.05244675
Topological Polar Surface Area:106
Heavy Atom Count:17
Complexity:327
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Price Analysis
Drug Function and Efficacy
It acts on dihydrofolate synthase, interfering with the first step in the synthesis of folic acid, and has a synergistic antibacterial effect when used in combination with trimethoprim.
Registered Holders
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ANDHRA ORGANICS LTD
Active
United States
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China Resources Double-Crane Pharmaceutical Co., Ltd.
Active
China
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Shanghai Liuhetang Biotechnology Xiangcheng Pharmaceutical Co., Ltd.
Active
China
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