Structure via PubChem · Public domain (PubChem)
sulfamethoxazole
Sign in to saveAlso known as Ro-42130, Urobak, SMZ, Sinomin, Gantanol, Gantanol-Ds, SMX, Gantanol (tn)
Sulfamethoxazole (SMZ or SMX) is an antibiotic. It is used for bacterial infections such as urinary tract infections, bronchitis, and prostatitis and is effective against both gram negative and positive bacteria such as Escherichia coli and Listeria monocytogenes.
Chemical data
- Formula
- C10H11N3O3S
- Molecular weight
- 253.28 g/mol
- IUPAC name
- 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
- SMILES
- CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
- InChIKey
- JLKIGFTWXXRPMT-UHFFFAOYSA-N
- XLogP
- 0.9
- Polar surface area
- 107 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Research
27,277 papersvia PubMed
Wikidata facts
- Mass
- 253.052
- Has use
- medication
Show 8 more facts
- Commons category
- Sulfamethoxazole
- chemical formula
- C₁₀H₁₁N₃O₃S
- canonical SMILES
- CC1=CC(=NO1)NS(=O)(=O)C2=CC=C(C=C2)N
- defined daily dose
- 2
- MCN code
- 2935.90.25
- subject has role
- antibiotic
- has characteristic
- bitterness
- significant drug interaction
- glimepiride
via Wikidata · CC0
~5 min read
Encyclopedic overview
6 sectionsContents
- Side effects
- Mechanism of action
- Pharmacokinetics
- See also
- Notes
- External links
Sulfamethoxazole (SMZ or SMX) is an antibiotic. It is used for bacterial infections such as urinary tract infections, bronchitis, and prostatitis and is effective against both gram negative and positive bacteria such as Escherichia coli and Listeria monocytogenes.
Common side effects include nausea, vomiting, loss of appetite, and skin rashes. It is a sulfonamide and bacteriostatic. It resembles a component of folic acid. It prevents folic acid synthesis in the bacteria that must synthesize their own folic acid. Mammalian cells, and some bacteria, do not synthesize but require preformed folic acid (vitamin B9); they are therefore insensitive to sulfamethoxazole.
Excerpted from Wikipedia’s “sulfamethoxazole” article, available under the CC BY-SA 4.0 licence.