Sulfamethoxazole Systematic (IUPAC) name 4-amino-N-(5-methylisoxazol-3-yl)-benzenesulfonamide Clinical data AHFS/Drugs.com Pregnancy cat. C (Australia, United States) Legal status Prescription Only (S4) (AU) ℞-only Routes Oral, IV Pharmacokinetic data Protein binding 70% Metabolism Hepatic acetylation and glucuronidation Half-life 10 hours Excretion Renal Identifiers CAS number ATC code J01 QJ01 PubChem DrugBank ChemSpider UNII KEGG ChEBI ChEMBL Chemical data Formula C10H11N3O3S Mol. mass 253.279 g/mol SMILES & Physical data Melt. point 169 °C (336 °F) (what is this?)
It is most often used as part of a synergistic combination with trimethoprim in a 5:1 ratio in co-trimoxazole (abbreviated SMZ-TMP and SMX-TMP, or TMP-SMZ and TMP-SMX), also known under trade names such as Bactrim, Septrin, or Septra; in Eastern Europe it is marketed as Biseptol. Its primary activity is against susceptible forms of Streptococcus, Staphylococcus aureus (including MRSA), Escherichia coli, Haemophilus influenzae, and oral anaerobes. It is commonly used to treat urinary tract infections. In addition it can be used as an alternative to amoxicillin-based antibiotics to treat sinusitis. It can also be used to treat toxoplasmosis and it is the drug of choice for Pneumocystis pneumonia, which affects primarily patients with HIV.
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. 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 is caused by mutations in the enzymes involved in folic acid synthesis that prevent the drug from binding to it.
A TMP-SMZ (also TMP-SMX or TMP-Sulfa) disk is a combination of trimethoprim and sulfamethoxazole that acts synergistically for bactericidal action. A bacterial culture impregnated with a trimethoprim and sulfamethoxazole disk may be used to help identify an organism as Gardnerella vaginalis; it is sensitive to the TMP-SMZ disk.
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. Sulfamethoxazole is also a Stevens–Johnson syndrome (SJS) inducing substance.
Sulfamethoxazole can also cause nausea, severe stomach, or abdomen pains. Headaches commonly occur when taking sulfamethoxazole. Muscle pains sometimes occur when taking this medicine. If symptoms persist, one should contact his/her physician. If trouble breathing or swelling of the face, mouth, or tongue occurs, one should discontinue the medicine and get emergency medical help. These are often symptoms of a severe allergic reaction.
Sulfamethoxazole/trimethoprim can lead to a megaloblastic anemia in some patients because it is a folate antagonist.
- ^ Ma, M.; Cheng, Y.; Xu, Z.; Xu, P.; Qu, H.; Fang, Y.; Xu, T.; Wen, L. (2007). "Evaluation of polyamidoamine (PAMAM) dendrimers as drug carriers of anti-bacterial drugs using sulfamethoxazole (SMZ) as a model drug". European journal of medicinal chemistry 42 (1): 93–8. doi:10.1016/j.ejmech.2006.07.015. PMID 17095123.
- ^ Garg, S.K.; Ghosh, S.S.; Mathur, V.S. (1986). "Comparative pharmacokinetic study of four different sulfonamides in combination with trimethoprim in human volunteers". International journal of clinical pharmacology, therapy, and toxicology 24 (1): 23–5. PMID 3485584.
- ^ SMZ in Abstract of "Rat model of concurrent Pneumocystis carinii (Pc), Toxoplasma gondii (Tg), and Mycobacterium avium complex (MAC) infections for assessment of multiple prophylaxis" at ncbi.nlm.nih.gov
- ^ SMZ-TMP in Abstract of "Cutaneous hypersensitivity to sulfamethoxazole-trimethoprim (SMZ TMP) in HIV infected patients" at nlm.nih.gov
- ^ BIAM, "Sulfamethoxazole"
- ^ PubChem, "Sulfamethoxazole - Substance Summary"
- ^ ChemDB, "Sulfamethoxazole"
- ^ Sulfamethazole in "Clinical Diabetes: Case Study: A 90-Year-Old Man With Confusion and Night Sweats", and "Chronic Granulomatous Disease"
- ^ Martindale, The extra pharmacopoeia, 30th ed, p. 208
- ^ USMLE World Step1, Qbank Pharmacology, 2009, Q106
- BIAM. "Sulfamethoxazole" (in French), Banque d'Informations Automatisée sur les Médicaments (drugs database), last updated December 21, 2000
- ChemDB. "Sulfamethoxazole", ChemDB, National Institute of Allergy and Infectious Diseases (NIAID), National Institutes of Health (NIH)
- PubChem. "Sulfamethoxazole - Substance Summary", PubChem, National Center for Biotechnology Information (NCBI), National Library of Medicine (NLM), National Institutes of Health (NIH)
- Sulfamethoxazole in the ChemIDplus database
Antibacterials: nucleic acid inhibitors (J01E, J01M) Antifolates
DNA and RNA synthesis)Sulfonamides
DNA replication)1st g.2nd g.3rd g.4th g.Vet.Related (DG)
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sulfamethoxazole — noun Etymology: sulfa + methyl + oxazole, a compound C3H3NO (from International Scientific Vocabulary ox + azole) Date: 1960 an antibacterial sulfonamide C10H11N3O3S used alone or in combination with trimethoprim (as in the treatment of urinary… … New Collegiate Dictionary
sulfamethoxazole — /sul feuh meth ok seuh zohl /, n. Pharm. an antimicrobial substance, C10H11N3O3S, used against a variety of susceptible Gram positive and Gram negative organisms, as in the treatment of certain urinary tract infections and skin infections. [1955… … Universalium
sulfamethoxazole — noun A particular kind of antibiotic, an antibacterial sulfonamide … Wiktionary
sulfamethoxazole — A sulfonamide related chemically to sulfisoxazole, with a similar antibacterial spectrum, but a slower rate of absorption from the gastrointestinal tract and urinary excretion. * * * sul·fa·meth·ox·a·zole or chiefly Brit sul·pha·meth·ox·a·zole… … Medical dictionary
sulfamethoxazole — sul·fa·meth·oxazole … English syllables
sulfamethoxazole — sulphamethoxazole; n.; see co trimoxazole, sulphonamide … The new mediacal dictionary
sulfamethoxazole — sul•fa•meth•ox•a•zole [[t]ˌsʌl fə mɛθˈɒk səˌzoʊl[/t]] n. pha an antimicrobial substance, C10H11N3O3used to treat urinary tract and skin infections • Etymology: 1955–60; sulfa (nilamide) +meth ( yl) +(is)oxazole … From formal English to slang
sulfamethoxazole — noun a sulfonamide (trade name Gantanol) used to treat infections (especially infections of the urinary tract) • Syn: ↑Gantanol • Hypernyms: ↑sulfa drug, ↑sulfa, ↑sulpha, ↑sulfonamide … Useful english dictionary
Trimethoprim/sulfamethoxazole — Combination of Trimethoprim Dihydrofolate reductase inhibitor (16.7%) Sulfamethoxazole Sulfonamide antibiotic (83.3%) … Wikipedia
trimethoprim-sulfamethoxazole — noun A combination of trimethoprim and sulfamethoxazole in the ratio of 1 to 5. Syn: TMP SMX, co trimoxazole … Wiktionary