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CAS 80-23-9

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3-amino-4-hydroxy-N-methylbenzenesulfonamide

Description:
3-Amino-4-hydroxy-N-methylbenzenesulfonamide, commonly known as sulfamethoxazole, is a sulfonamide antibiotic that exhibits bacteriostatic properties by inhibiting bacterial folic acid synthesis. This compound features a sulfonamide group, which is essential for its antimicrobial activity, and contains both amino and hydroxy functional groups that contribute to its solubility and reactivity. It is typically a white to off-white crystalline powder, soluble in water and organic solvents, making it suitable for various pharmaceutical formulations. The compound is often used in combination with trimethoprim to enhance its efficacy against a broad spectrum of bacterial infections. Its mechanism of action involves competitive inhibition of the enzyme dihydropteroate synthase, which is crucial in the bacterial synthesis of folate. Additionally, sulfamethoxazole has a relatively low toxicity profile, but it can cause allergic reactions in some individuals. It is important to note that while effective, the use of this antibiotic should be guided by susceptibility testing to prevent the development of resistance.
Formula:C7H10N2O3S
InChI:InChI=1/C7H10N2O3S/c1-9-13(11,12)5-2-3-7(10)6(8)4-5/h2-4,9-10H,8H2,1H3
InChI key:InChIKey=NFNLMGYLSDEJKS-UHFFFAOYSA-N
SMILES:S(NC)(=O)(=O)C1=CC(N)=C(O)C=C1
Synonyms:
  • 1-Phenol-4-sulfonamide, 2-amino-N-methyl-
  • 2-Amino-4-(methylsulfamoyl)phenol
  • 2-Amino-N-methyl-1-phenol-4-sulfonamide
  • 2-Aminophenol-4-Sulfonmethylamide
  • 2-Aminophenol-4-Sulfonmethylaminde
  • 2-Aminophenol-4-sulfomethylamide
  • 2-Aminophenol-4-sulfonic acid methylamide
  • 2-Aminophenol-N-methyl-4-sulfoamide
  • 3-Amino-4-Hydroxy-N-Methyl-Benzenesulfonamide
  • 3-Amino-4-hydroxy-N-methylbenzene-1-sulfonamide
  • See more synonyms
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