Sulfamethoxazole
You don't need to be Editor-In-Chief to add or edit content to WikiDoc. You can begin to add to or edit text on this WikiDoc page by clicking on the edit button at the top of this page. Next enter or edit the information that you would like to appear here. Once you are done editing, scroll down and click the Save page button at the bottom of the page.
| Image:Sulfamethoxazole.png | |
| Sulfamethoxazole
| |
| Systematic (IUPAC) name | |
| 4-amino-N-(5-methylisoxazol-3-yl)-benzenesulfonamide | |
| Identifiers | |
| CAS number | |
| ATC code | J01 |
| PubChem | |
| DrugBank | |
| Chemical data | |
| Formula | C10H11N3O3S |
| Mol. mass | 253.279 g/mol |
| SMILES | & |
| 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 |
Prescription Only (S4)(AU) ℞-only |
| Routes | Oral |
|
WikiDoc Resources for Sulfamethoxazole | |
|
Articles | |
|---|---|
|
Most recent articles on Sulfamethoxazole Most cited articles on Sulfamethoxazole | |
|
Media | |
|
Powerpoint slides on Sulfamethoxazole | |
|
Evidence Based Medicine | |
|
Clinical Trials | |
|
Ongoing Trials on Sulfamethoxazole at Clinical Trials.gov Trial results on Sulfamethoxazole Clinical Trials on Sulfamethoxazole at Google
| |
|
Guidelines / Policies / Govt | |
|
US National Guidelines Clearinghouse on Sulfamethoxazole NICE Guidance on Sulfamethoxazole
| |
|
Books | |
|
News | |
|
Commentary | |
|
Definitions | |
|
Patient Resources / Community | |
|
Patient resources on Sulfamethoxazole Discussion groups on Sulfamethoxazole Patient Handouts on Sulfamethoxazole Directions to Hospitals Treating Sulfamethoxazole Risk calculators and risk factors for Sulfamethoxazole
| |
|
Healthcare Provider Resources | |
|
Causes & Risk Factors for Sulfamethoxazole | |
|
Continuing Medical Education (CME) | |
|
International | |
|
| |
|
Business | |
|
Experimental / Informatics | |
Please Take Over This Page and Apply to be Editor-In-Chief for this topic: There can be one or more than one Editor-In-Chief. You may also apply to be an Associate Editor-In-Chief of one of the subtopics below. Please mail us [1] to indicate your interest in serving either as an Editor-In-Chief of the entire topic or as an Associate Editor-In-Chief for a subtopic. Please be sure to attach your CV and or biographical sketch.
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, Septrin, or Septra (also abbreviated SMX/TMP). Its primary activity is against susceptible forms of Streptococcus, Staphylococcus aureus, Escherichia coli, Haemophilus influenzae, and oral anaerobes. It is commonly used to treat urinary tract infections. In addition can be used as an alternative to amoxicillin-based antibiotics to treat sinusitis.
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. Bacterial resistance to sulfamethoxazole are caused by mutations in the folic acid enzyme that prevents the drug from binding and blocking folic acid synthesis.
Side effects
The most common side effect of sulfamethoxazole/trimethoprim is gastrointestinal upset. Allergies to sulfa-based medications typically cause skin rashes, hives, or trouble breathing or swallowing and warrant immediate discontinuation of the medication and contact with doctor immediately. Sulfamethoxazole/trimethoprim is also known to increase blood concentrations of the drug warfarin (U.S. brand name: Coumadin) and can cause an unexpected increase in clotting time and uncontrolled bleeding. Neutropenia and thrombocytopenia also are rare adverse effects to be monitored if a patient is placed on long-term therapy.
References
- ↑ Martindale, The extra pharmacopoeia, 30th ed, p. 208
External links
- briandeer.com Side-effects information.
See also
Antibacterials for systemic use: sulfonamides (sulfa drugs) and trimethoprim (J01E) | |
|---|---|
| Trimethoprim and derivatives | Trimethoprim • Brodimoprim |
| Short-acting sulfonamides | Sulfaisodimidine • Sulfamethizole • Sulfadimidine • Sulfapyridine • Sulfafurazole • Sulfanilamide • Sulfathiazole • Sulfathiourea |
| Intermediate-acting sulfonamides | Sulfamethoxazole • Sulfadiazine • Sulfamoxole |
| Long-acting sulfonamides | Sulfadimethoxine • Sulfalene • Sulfametomidine • Sulfametoxydiazine • Sulfamethoxypyridazine • Sulfaperin • Sulfamerazine • Sulfaphenazole • Sulfamazon |
| Combinations | Sulfamethoxazole and trimethoprim |
| Other | Mafenide • Prontosil • Sulfacetamide • Sulfasalazine • Sulfisoxazole |
de:Sulfamethoxazol sk:Sulfametoxazol th:ซัลฟาเมโทซาโซล
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
