Sulfamethoxazole
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Sulfamethoxazole
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| Systematic (IUPAC) name | |
| 4-amino-N-(5-methylisoxazol-3-yl)-benzenesulfonamide | |
| Identifiers | |
| CAS number | 723-46-6 |
| ATC code | J01EC01 |
| PubChem | 5329 |
| DrugBank | APRD00076 |
| Chemical data | |
| Formula | C10H11N3O3S |
| Mol. weight | 253.279 g/mol |
| SMILES | CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N |
| Physical data | |
| Melt. point | 3 °C (37 °F) |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Protein binding | 70% |
| Metabolism | Hepatic acetylation and glucuronidation |
| Half life | 10 hours |
| Excretion | Renal |
| Therapeutic considerations | |
| Pregnancy cat. | |
| Legal status |
℞-only |
| Routes | Oral |
Sulfamethoxazole is a sulfonamide bacteriostatic antibiotic. It is most often used as part of a synergistic combination with trimethoprim in a 5:1 ratio in co-trimoxazole, which is also known as Bactrim or Septrin. It can be used as an alternative to amoxicillin-based antibiotics to treat sinusitis.
[edit] Mechanism of action
Sulfonamides are structural analogs and competitive antagonists of para-aminobenzoic acid (PABA). They inhibit normal bacterial utilization of PABA for the synthesis of folic acid, an important metabolite in DNA synthesis.[1] The effects seen are usually bacteriostatic in nature. Folic acid is not synthesized in humans, but is instead a dietary requirement. This allows for the selective toxicity to bacterial cells (or any cell dependent on synthesizing folic acid) over human cells.
[edit] References
- ^ Martindale, The extra pharmacopoeia, 30th ed, p. 208
[edit] See also
| Sulfonamides (J01E) edit | ||
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Mafenide, Prontosil, Sulfacetamide, Sulfamethizole, Sulfamethoxazole (with Trimethoprim in Co-trimoxazole), Sulfanilimide, Sulfasalazine, Sulfisoxazole |
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