Sulfamethazine
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04532 |
| CAS | 57-68-1 |
| Molecular Weight | 278.33 |
| Molecular Formula | C12H14N4O2S |
| Purity | >98% |
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Description
Sulfamethazine is a sulfonamide antibacterial agent that competitively inhibits dihydrospteric acid synthase, blocks the synthesis of folic acid and inhibits growth and proliferation. It can be used to treat pasteurosis, mastitis, urinary tract infections caused by sensitive bacteria in livestock, and can also be used for swine atrophic rhinitis, streptococcal disease, swine toxoplasmosis and coccidiosis.
Specification
| Related CAS | 1981-58-4 (sodium) |
| Synonyms | HSDB 4157; HSDB-4157; HSDB4157; Sulfadimidine; Intradine; Kelametazine; 4-Amino-N-(4,6-Dimethyl-2-pyrimidinyl)benzenesulfonamide; Azolmetazin; Diazil |
| Storage | Store at 2-8°C |
| IUPAC Name | 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide |
| Canonical SMILES | CC1=CC(=NC(=N1)NS(=O)(=O)C2=CC=C(C=C2)N)C |
| 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) |
| InChI Key | ASWVTGNCAZCNNR-UHFFFAOYSA-N |
| Source | Synthetic |
Properties
| Appearance | White to Off-white Solid |
| Application | Anti-infective agents |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 526.2°C at 760 mmHg |
| Melting Point | 197-200°C |
| Density | 1.392 g/cm3 |
| Solubility | Slightly soluble in DMSO, Methanol |
Reference Reading
1.Pyrite as a sustainable catalyst in electro-Fenton process for improving oxidation of sulfamethazine. Kinetics, mechanism and toxicity assessment.
Barhoumi N1, Oturan N2, Olvera-Vargas H2, Brillas E3, Gadri A4, Ammar S5, Oturan MA6. Water Res. 2016 May 1;94:52-61. doi: 10.1016/j.watres.2016.02.042. Epub 2016 Feb 18.
The degradation of 0.20 mM sulfamethazine (SMT) solutions was investigated by heterogeneous electro-Fenton (EF) process using pyrite as source of Fe(2+) (catalyst) and pH regulator in an undivided electrochemical cell equipped either with a Pt or a BDD anode and carbon-felt as cathode. Effect of pyrite concentration and applied current on the oxidative degradation kinetics and mineralization efficiency has been studied. The higher oxidation power of the process, named "Pyrite-EF″ using BDD anode was demonstrated. Pyrite-EF showed a better performance for the oxidation/mineralization of the drug SMT in comparison to the classic EF process: 95% and 87% TOC removal by Pyrite-EF with BDD and Pt anodes, respectively, versus 90% and 83% by classical EF with BDD and Pt anodes, respectively. The rate constant of the oxidation of SMT by OH was determined by the competition kinetics method and found to be 1.87 × 10(9) mol(-1) L s(-1). Based on the identified reaction intermediates by HPLC and GS-MS, as well as released SO4(2-), NH4(+) and NO3(-) ions, a plausible reaction pathway was proposed for the mineralization of SMT during Pyrite-EF process.
2.Effect of pH and soil structure on transport of sulfonamide antibiotics in agricultural soils.
Park JY1, Huwe B2. Environ Pollut. 2016 Mar 17;213:561-570. doi: 10.1016/j.envpol.2016.01.089. [Epub ahead of print]
We investigated the effect of solution pH and soil structure on transport of sulfonamide antibiotics (sulfamethoxazole, sulfadimethoxine and sulfamethazine) in combination with batch sorption tests and column experiments. Sorption isotherms properly conformed to Freundlich model, and sorption potential of the antibiotics is as follows; sulfadimethoxine > sulfamethoxazole > sulfamethazine. Decreasing pH values led to increased sorption potential of the antibiotics on soil material in pH range of 4.0-8.0. This likely resulted from abundance of neutral and positive-charged sulfonamides species at low pH, which electrostatically bind to sorption sites on soil surface. Due to destruction of macropore channels, lower hydraulic conductivities of mobile zone were estimated in the disturbed soil columns than in the undisturbed soil columns, and eventually led to lower mobility of the antibiotics in disturbed column. The results suggest that knowledge of soil structure and solution condition is required to predict fate and distribution of sulfonamide antibiotics in environmental matrix.
3.Transport of Three Antimicrobials in Runoff from Windrows of Composting Beef Cattle Manure.
Sura S, Degenhardt D, Cessna AJ, Larney FJ, Olson AF, McAllister TA. J Environ Qual. 2016 Mar;45(2):494-502. doi: 10.2134/jeq2015.05.0254.
Rain runoff from windrowed or stockpiled manure may contain antimicrobials with the potential to contaminate surface and ground water. To quantify the concentration of antimicrobials transported in runoff from windrowed manure, antimicrobials were administered continuously in feed to beef cattle () as follows: 44 mg of chlortetracycline kg feed (dry weight), a 1:1 mixture of 44 mg of chlortetracycline and 44 mg sulfamethazine kg feed, and 11 mg of tylosin kg feed. Cattle in a fourth treatment group received no antimicrobials (control). Manure from the cattle was used to construct two windrows per treatment. On Days 2 and 21 of composting, a portable Guelph Rainfall Simulator II was used to apply deionized water at an intensity of 127 mm h to each windrow, and the runoff was collected. Manure samples were collected before rain simulations on Days 2 and 21 of composting for antimicrobial analysis. On Day 2, average concentrations of chlortetracycline, sulfamethazine, and tylosin in manure were 2580, 450, and 120 μg kg, respectively, with maximum concentrations in runoff of 2740, 3600, and 4930 μg L, respectively.
4.Dissipation of Antimicrobials in Feedlot Manure Compost after Oral Administration versus Fortification after Excretion.
Amarakoon ID, Zvomuya F, Sura S, Larney FJ, Cessna AJ, Xu S, McAllister TA. J Environ Qual. 2016 Mar;45(2):503-10. doi: 10.2134/jeq2015.07.0408.
Fortification of manure with antimicrobials is one approach to studying their dissipation. However, fortified antimicrobials may not accurately model dissipation that occurs after antimicrobials have been administered to livestock in feed and excreted in manure. This study examined the dissipation of antimicrobials excreted in manure versus those added directly to manure (fortified). Steers were fed a diet containing (kg feed) (i) 44 mg chlortetracycline, (ii) 44 mg each of chlortetracycline and sulfamethazine, (iii) 11 mg tylosin, and (iv) no antimicrobials (control). Fortified antimicrobial treatments were prepared by adding antimicrobials to control manure. Manure was composted for 30 d, sampled every 2 to 3 d, and analyzed for antimicrobials and compost properties. Antimicrobial dissipation followed first-order kinetics. The dissipation rate constant was significantly greater (based on 95% confidence limit) for excreted (0.29-0.54 d) than for fortified chlortetracycline (0.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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