Sulfamethoxazole (also known as RP 2145; trade names: Rufol; Salimol ), a sulfonamide bacteriostatic antibiotic, is widely used for bacterial infections such as urinary tract infections, bronchitis, and prostatitis and is effective against both gram negative and positive bacteria such as Listeria monocytogenes and E. coli. Common side effects include nausea, vomiting, loss of appetite, and a rash. It is a sulfonamide and bacteriostatic.
Physicochemical Properties
| Molecular Formula | C10H11N3O3S |
| Molecular Weight | 253.2776 |
| Exact Mass | 253.052 |
| Elemental Analysis | C, 47.42; H, 4.38; N, 16.59; O, 18.95; S, 12.66 |
| CAS # | 723-46-6 |
| Related CAS # | Sulfamethoxazole-d4;1020719-86-1;Sulfamethoxazole-13C6;1196157-90-0;Sulfamethoxazole sodium;4563-84-2 |
| Appearance | White to off-white solid powder |
| Density | 1.5±0.1 g/cm3 |
| Boiling Point | 482.1±55.0 °C at 760 mmHg |
| Melting Point | 166 °C |
| Flash Point | 245.4±31.5 °C |
| Vapour Pressure | 0.0±1.2 mmHg at 25°C |
| Index of Refraction | 1.641 |
| LogP | 0.89 |
| SMILES | S(C1C([H])=C([H])C(=C([H])C=1[H])N([H])[H])(N([H])C1C([H])=C(C([H])([H])[H])ON=1)(=O)=O |
| InChi Key | JLKIGFTWXXRPMT-UHFFFAOYSA-N |
| InChi Code | 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) |
| Chemical Name | 4-amino-N-(5-methylisoxazol-3-yl)benzenesulfonamide |
| Synonyms | RP-2145; RP2145; RP 2145; trade names: Rufol; Salimol |
| HS Tariff Code | 2934.99.4400 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | Antibacterial |
| ln Vitro | Para-aminobenzoic acid (PABA) has structural analogs and competitive antagonists in the form of sulfonamides. They prevent bacteria from using PABA normally to synthesis folic acid, a crucial metabolite for DNA synthesis. ? Most of the time, the effects are bacteriostatic. Humans cannot synthesize folic acid; instead, they must consume it through diet. This enables the selective toxicity against human cells to bacterial cells, or any other cell that depends on folic acid synthesis. Mutations in the enzymes responsible for folic acid synthesis lead to bacterial resistance to sulfamethoxazole by preventing the drug from binding to it. |
| References |
[1]. Aquatic environmental risk assessment for human use of the old antibiotic sulfamethoxazole in Europe. Environ Toxicol Chem. 2016 Apr;35(4):767-79. [2]. Transcriptional profile of the human pathogenic fungus Paracoccidioides lutzii in response to sulfamethoxazole. Med Mycol. 2015;53(5):477-492. |
Solubility Data
| Solubility (In Vitro) |
DMSO : 51~100 mg/mL ( 201.35~394.82 mM ) Ethanol : ~23 mg/mL H2O: ~0.1 mg/mL (~0.39 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.87 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (9.87 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (9.87 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9482 mL | 19.7410 mL | 39.4820 mL | |
| 5 mM | 0.7896 mL | 3.9482 mL | 7.8964 mL | |
| 10 mM | 0.3948 mL | 1.9741 mL | 3.9482 mL |