Sulfamethoxazole
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| Category | Antibiotics |
| Catalog number | BBF-03935 |
| CAS | 723-46-6 |
| Molecular Weight | 253.28 |
| Molecular Formula | C10H11N3O3S |
| Purity | >98% |
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Description
Sulfamethoxazole is a sulfonamide bacteriostatic antibiotic with an IC50 of 2.7 μM. It is effective against both gram-negative and -positive bacteria. It is used for urinary tract infections, respiratory system infections, intestinal infections, biliary tract infections and local soft tissue or wound infections caused by sensitive bacteria.
Specification
| Synonyms | RP-2145; RP2145; RP 2145; Rufol; Salimol |
| Storage | Store at 2-8°C |
| IUPAC Name | 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide |
| Canonical SMILES | CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N |
| InChI | InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13) |
| InChI Key | JLKIGFTWXXRPMT-UHFFFAOYSA-N |
| Source | Synthetic |
Properties
| Appearance | White to Off-white Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 482.1°C at 760 mmHg |
| Melting Point | 168-172°C |
| Flash Point | 245.4ºC |
| Density | 1.462 g/cm3 |
| Solubility | Soluble in Acetone |
| LogP | 3.10100 |
Reference Reading
1.Fate of sulfamethoxazole, its main metabolite N-ac-sulfamethoxazole and ciprofloxacin in agricultural soils amended or not by organic waste products.
Andriamalala A;Vieublé-Gonod L;Dumeny V;Cambier P Chemosphere. 2018 Jan;191:607-615. doi: 10.1016/j.chemosphere.2017.10.093. Epub 2017 Oct 16.
Spreading organic waste products (OWP) issued from sewage sludge or manures into soil may disseminate antibiotics with unknown risks for human health and environment. Our objectives were to compare the fate of two sulfonamides, sulfamethoxazole (SMX) and its metabolite N-acetyl-sulfamethoxazole (N-ac-SMX), and one fluoroquinolone, ciprofloxacin (CIP), in an unamended soil, and two soils regularly amended since 1998 with a sewage sludge and green waste compost and with farmyard manure respectively. Incubations of soil spiked with ;14;C labelled SMX or N-ac-SMX (0.02 mg kg;-1;) or CIP (0.15 mg kg;-1;) allowed a quantification of radiolabeled molecules in the mineralized, easily, hardly and non-extractable fractions after 3 and 156 days. Nature of ;14;C molecules was also analyzed by HPLC in extractable fractions after 3 and 156 days. SMX and N-ac-SMX dissipation was fast and due to i) mineralization (∼10% of recovered ;14;C after 156 days) or incomplete degradation (production of metabolites), ii) adsorption, even if both sulfonamides present low Kd (<3 L kg;-1;) and iii) formation of non-extractable residues (NER), representing more than 50% of recovered radioactivity. N-ac-SMX was more mineralized than SMX, and formed more progressively NER, after a step of deacetylation.
2.Toxicity of the micropollutants Bisphenol A, Ciprofloxacin, Metoprolol and Sulfamethoxazole in water samples before and after the oxidative treatment.
Richard J;Boergers A;Vom Eyser C;Bester K;Tuerk J Int J Hyg Environ Health. 2014 Apr-May;217(4-5):506-14. doi: 10.1016/j.ijheh.2013.09.007. Epub 2013 Oct 9.
The amount of organic micropollutants detected in surface waters increases steadily. Common waste water treatment plants are not built to remove these substances. Thus there is a need for new technologies. A promising technology is the use of advanced oxidation processes through which organic micropollutants can be removed from waste water. However, the formation of oxidation by-products is likely and needs to be investigated since the by-products not only differ from their parent compounds in regard to their chemical and physical properties but they can also differ in toxicity. Therefore this study was designed to combine chemical and toxicological analyses of the advanced oxidation (O3 [5mg/L] or UV/H2O2 [Hg-LP lamp; 15W; 1g/L H2O2]) of waste water treatment plant effluents and pure water. Effluent samples from conventional activated sludge waste water treatment (mechanical treatment, activated sludge basin, and primary as well as secondary treatment steps) and high-purity deionized water (pure water) were spiked with Bisphenol A, Ciprofloxacin, Metoprolol or Sulfamethoxazole and treated with O3 or UV/H2O2. For the toxicological analyses mammalian cells (CHO-9, T47D) were exposed to the water samples for 24h and were tested for cytotoxicity (MTT Test), genotoxicity (Alkaline Comet Assay) and estrogenicity (ER Calux(®)).
3.Antibiofilm effect of antimicrobials used in the therapy of mycobacteriosis.
Flores VD;Siqueira FD;Mizdal CR;Bonez PC;Agertt VA;Stefanello ST;Rossi GG;Campos MM Microb Pathog. 2016 Oct;99:229-235. doi: 10.1016/j.micpath.2016.08.017. Epub 2016 Aug 20.
Rapidly growing mycobacteria (RGM) are opportunistic pathogens found in the environment. When in biofilms, mycobacteria is highly resistant to antibacterial treatments. The purpose of this study is to evaluate the antibiofilm activity of antimicrobials commonly used in therapy against mycobacteria. The antimicrobial susceptibility of Mycobacterium abscessus, Mycobacterium fortuitum and Mycobacterium massiliense was determined in planktonic and sessile populations. The antimicrobials amikacin, ciprofloxacin, clarithromycin, doxycycline, imipenem and sulfamethoxazole were tested. For each drug, it was evaluated the susceptibility of the pathogen, the ability to inhibit biofilm formation and the resistance of biofilms to antimicrobial activity. Results showed although, the antimicrobials tested are used as an alternative therapy for RGM, M. abscessus proved to be resistant to clarithromycin, beside that, M. massiliense showed a resistant profile to clarithromycin and sulfamethoxazole. Moreover, the inhibition of biofilm formation and its destruction have not been fully met. Considering that the biofilms are a known form of bacterial resistance, the failure of alternatives to inhibit or destroy biofilms can trigger the recurrence of infections.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
