User:Bunny.Grp4/sandbox
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| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
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| Routes of administration | Oral, IV |
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| Protein binding | 70% |
| Metabolism | Hepatic acetylation and glucuronidation |
| Elimination half-life | 10 hours |
| Excretion | Renal |
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| Formula | C10H11N3O3S |
| Molar mass | 253.279 g/mol g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 169 °C (336 °F) |
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Sulfamethoxazole (abbreviated SMZ and SMX)[1][2][3], also known as Gantanol (trade name), is a sulfonamide bacteriostatic antibiotic introduced to the United States in 1961[4] that is discontinued.[5][6] It is now commonly used as part of a synergistic combination with trimethoprim (abbreviated SMZ-TMP and SMX-TMP,[7] or TMP-SMZ and TMP-SMX), also known under trade names such as Bactrim, Bactrim DS, Septra DS, or Sulfatrim.[8]
It was used for bacterial infections such as urinary tract infections, bronchitis, and prostatitis and is affective against both gram negative and positive bacteria such as Listeria monocytogenes and E. coli.[6]
Other names include: sulfamethalazole, sulfisomezole, MS 53, RO 4 2130[9][10] and sulfamethazole.[11]
Side effects[edit]
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.[citation needed]
Sulfamethoxazole can also cause nausea or severe stomach or abdominal pain. Headaches commonly occur when taking sulfamethoxazole. Muscle pain sometimes occurs when taking this medication. 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 medication and get emergency medical help. These are often symptoms of a severe allergic reaction (anaphylaxis).
Sulfamethoxazole/trimethoprim can lead to a megaloblastic anemia in some patients because it is a folate antagonist.[12]
Mechanism of action[edit]
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.[13] 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(combination of both is known as cotrimoxazole) 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.
See also[edit]
Notes[edit]
- ^ 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
- ^ Pharmaceutical Manufacturing Encyclopedia, 3rd Edition. William Andrew Publishing. 22 October 2013. ISBN 9780815518563.
- ^ "Sulfamethoxazole". Drugs@FDA. Retrieved 5 November 2015.
- ^ a b "Sulfamethoxazole". DrugBank. Retrieved 5 November 2015.
- ^ SMZ-TMP in Abstract of "Cutaneous hypersensitivity to sulfamethoxazole-trimethoprim (SMZ TMP) in HIV infected patients" at nlm.nih.gov
- ^ Williams, Eni. "sulfamethoxazole and trimethoprim, Bactrim, Septra". MedicineNet.com. Retrieved 5 November 2015.
- ^ PubChem. "Sulfamethoxazole - Substance Summary", PubChem, National Center for Biotechnology Information (NCBI), National Library of Medicine (NLM), National Institutes of Health (NIH)
- ^ ChemDB. "Sulfamethoxazole", ChemDB, National Institute of Allergy and Infectious Diseases (NIAID), National Institutes of Health (NIH)
- ^ Sulfamethazole in "Clinical Diabetes: Case Study: A 90-Year-Old Man With Confusion and Night Sweats", and "Chronic Granulomatous Disease"
- ^ USMLE World Step1, Qbank Pharmacology, 2009, Q106
- ^ Martindale, The extra pharmacopoeia, 30th ed, p. 208
External links[edit]
- Sulfamethoxazole in the ChemIDplus database
Category:Anilines Category:Aromatic amines Category:Isoxazoles Category:Sulfonamide antibiotics Category:Dihydropteroate synthetase inhibitors Category:Equine medications