Sulfamethoxazole: Difference between revisions
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'''Sulfamethoxazole''' is a [[Sulfonamide (medicine)|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]]. | '''Sulfamethoxazole''' is a [[Sulfonamide (medicine)|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]]. | ||
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Revision as of 16:23, 20 August 2012
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| Pregnancy category | |
| Routes of administration | Oral |
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| Pharmacokinetic data | |
| Protein binding | 70% |
| Metabolism | Hepatic acetylation and glucuronidation |
| Elimination half-life | 10 hours |
| Excretion | Renal |
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| E number | {{#property:P628}} |
| ECHA InfoCard | {{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value). |
| Chemical and physical data | |
| Formula | C10H11N3O3S |
| Molar mass | 253.279 g/mol |
| 3D model (JSmol) | |
| Melting point | 3 °C (37.4 °F) |
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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]
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
Template:SulfonamideAntiBiotics
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