SulfamethazineCAS# 57-68-1 |
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Quality Control & MSDS
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Chemical structure
3D structure
| Cas No. | 57-68-1 | SDF | Download SDF |
| PubChem ID | 5327 | Appearance | Powder |
| Formula | C12H14N4O2S | M.Wt | 278.33 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Synonyms | Sulfadimidine; Sulfadimerazine | ||
| Solubility | DMSO : ≥ 100 mg/mL (359.29 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide | ||
| SMILES | CC1=CC(=NC(=N1)NS(=O)(=O)C2=CC=C(C=C2)N)C | ||
| Standard InChIKey | ASWVTGNCAZCNNR-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16) | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Sulfamethazine is a sulfonamide antibacterial.
Target: Antibacterial
Sulfamethazine is an antibiotic used to treat bronchitis, prostatitis and urinary tract infections. Sulfamethazine blocks the synthesis of dihydrofolic acid by inhibiting dihydropteroate synthase. In addition, sulfamethazine is a structural analog and competitive antagonist of para-aminobenzoic acid (PABA) and can inhibit normal bacterial utilization of PABA for the synthesis of folic acid, which is an important metabolite in DNA synthesis [1, 2]. References: | |||||
Sulfamethazine Dilution Calculator
Sulfamethazine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.5929 mL | 17.9643 mL | 35.9286 mL | 71.8571 mL | 89.8214 mL |
| 5 mM | 0.7186 mL | 3.5929 mL | 7.1857 mL | 14.3714 mL | 17.9643 mL |
| 10 mM | 0.3593 mL | 1.7964 mL | 3.5929 mL | 7.1857 mL | 8.9821 mL |
| 50 mM | 0.0719 mL | 0.3593 mL | 0.7186 mL | 1.4371 mL | 1.7964 mL |
| 100 mM | 0.0359 mL | 0.1796 mL | 0.3593 mL | 0.7186 mL | 0.8982 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Sulfamethazine is a sulfonamide antibacterial.
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Environmental behavior of sulfadiazine, sulfamethazine, and their metabolites.[Pubmed:28258427]
Environ Sci Pollut Res Int. 2017 Apr;24(10):9802-9812.
Sulfonamides are one of the most frequently used antibiotics worldwide. Therefore, processes that determine their fate in the environment are of great interest. In the present work, biodegradation as biotic process and hydrolysis and photolysis as abiotic processes were investigated. In biodegradation experiments, it was found out that sulfonamides (sulfadiazine and Sulfamethazine) and their N (4)-acetylated metabolites were not readily biodegradable. The results showed that decrease of concentrations were in the range from 4% for sulfadiazine to 22% for N (4)-acetylSulfamethazine. Hydrolytic experiments examined at pH values normally found in the environment also showed their resistance. However, photolysis proved to be significant process for decreasing concentrations of sulfonamides and their metabolites in three various aqueous matrices (Milli-Q water, river water, and synthetic wastewater). In addition, influence of ubiquitous water constituents (Cl(-), NO3(-), SO4(2-), PO4(3-), and humic acids) was also investigated, showing their different impact on photolysis of investigated pharmaceuticals. The results showed that photolysis followed first-order kinetics in all cases. The obtained results are very important for assesing the environmental fate of sulfonamides and their metabolites in the aquatic environment.
Sulfate radical-based oxidation of antibiotics sulfamethazine, sulfapyridine, sulfadiazine, sulfadimethoxine, and sulfachloropyridazine: Formation of SO2 extrusion products and effects of natural organic matter.[Pubmed:28363182]
Sci Total Environ. 2017 Sep 1;593-594:704-712.
The widespread occurrence of sulfonamide antibiotics in the environment has raised great concerns about their potential to proliferate antibacterial resistance. Sulfate radical (SO4(*-)) based advanced oxidation processes (SR-AOPs) are promising in-situ chemical oxidation (ISCO) technologies for remediation of soil and groundwater contaminated by antibiotics. The present study reported that thermally activated persulfate oxidation of sulfonamides (SAs) bearing six-membered heterocyclic rings, e.g., Sulfamethazine (SMZ), sulfapyridine (SPD), sulfadiazine (SDZ), sulfadimethoxine (SDM), and sulfachloropyridazine (SCP), all produced SO2 extrusion products (SEPs), a phenomenon that is of potential importance, but not systematically studied. As an electrophilic oxidant, SO4(*-) tends to attack the aniline moiety, the reactive site of SAs, via electro-transfer mechanism. The resulting anilinyl radical cations are subjected to further intermolecular Smiles-type rearrangement to produce SEPs. Formation of SEPs is expected to occur in other SR-AOPs as well. The temperature-dependent evolution pattern of SEP of SMZ, 4-(2-imino-4,6-dimethylpyrimidin-1(2H)-yl)aniline, can be well fitted by kinetic modeling concerning sequential formation and transformation of intermediate product. The presence of natural organic matter (NOM) influenced the evolution patterns of 4-(2-imino-4,6-dimethylpyrimidin-1(2H)-yl)aniline significantly. Toxicological effects of SEPs on ecosystem and human health remain largely unknown, thus, further monitoring studies are highly desirable.
Pyridine and 3-methylpyridine solvates of the triple sulfa drug constitutent sulfamethazine.[Pubmed:28035096]
Acta Crystallogr C Struct Chem. 2017 Jan 1;73(Pt 1):9-12.
Sulfonamides display a wide variety of pharmacological activities. Sulfamethazine [abbreviated as SMZ; systematic name 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide], one of the constitutents of the triple sulfa drugs, has wide clinical use. Pharmaceutical solvates are crystalline solids of active pharmaceutical ingredients (APIs) incorporating one or more solvent molecules in the crystal lattice, and these have received special attention, as the solvent molecule can impart characteristic physicochemical properties to APIs and solvates, therefore playing a significant role in drug development. The ability of SMZ to form solvates has been investigated. Both pyridine and 3-methylpyridine form solvates with SMZ in 1:1 molar ratios. The pyridine monosolvate, C12H14N4O2S.C5H5N, crystallizes in the orthorhombic space group Pna21, with Z = 8 and two molecules per assymetric unit, whereas the 3-methylpyridine monosolvate, C12H14N4O2S.C6H7N, crystallizes in the orthorhombic space group P212121, with Z = 4. Crystal structure analysis reveals intramolecular N-H...N hydrogen bonds between the molecules of SMZ and the pyridine solvent molecules. The solvent molecules in both structures play an active part in strong intermolecular interactions, thereby contributing significantly to the stability of both structures. Three-dimensional hydrogen-bonding networks exist in both structures involving at least one sulfonyl O atom and the amine N atom. In the pyridine solvate, there is a short pi-pi interaction [centroid-centroid distance = 3.926 (3) A] involving the centroids of the pyridine rings of two solvent molecules and a weak intermolecular C-H...pi interaction also contributes to the stability of the crystal packing.
Uptake and translocation of sulfamethazine by alfalfa grown under hydroponic conditions.[Pubmed:28372746]
J Environ Sci (China). 2017 Mar;53:217-223.
Antibiotics are routinely used in intensive animal agriculture operations collectively known as Concentrated Animal Feed Operations (CAFO) which include dairy, poultry and swine farms. Wastewater generated by CAFOs often contains low levels of antibiotics and is typically managed in an anaerobic lagoon. The objective of this research is to investigate the uptake and fate of aqueous Sulfamethazine (SMN) antibiotic by alfalfa (Medicago sativa) grass grown under hydroponic conditions. Uptake studies were conducted using hydroponically grown alfalfa in a commercially available nutrient solution supplemented with 10mg/L of SMN antibiotic. Analysis of alfalfa sap, root zone, middle one-third, and top portion of the foliage showed varying uptake rate and translocation of SMN. The highest average amount of SMN (8.58mug/kg) was detected in the root zone, followed by the top portion (1.89mug/kg), middle one-third (1.30mug/kg), and sap (0.38mug/kg) samples, indicating a clear distribution of SMN within the sampled regions. The ultraviolet (UV) spectra of parent SMN and translocated SMN identified in different parts of the plant present the possibility of metabolization during the uptake process. Uptake of SMN using alfalfa grown under hydroponic conditions has potential as a promising remediation technology for removal of similar antibiotics from wastewater lagoons.
