CAS 79-72-1
:5-Amino-2-methyl-N-phenylbenzenesulfonamide
Description:
5-Amino-2-methyl-N-phenylbenzenesulfonamide, commonly known as sulfamethoxazole, is a sulfonamide antibiotic characterized by its sulfonamide functional group, which is essential for its antibacterial activity. This compound features an amino group and a methyl group on the benzene ring, contributing to its solubility and biological activity. It is typically a white to off-white crystalline solid with moderate solubility in water, which enhances its bioavailability. The presence of the phenyl group increases its lipophilicity, allowing it to penetrate bacterial cell membranes effectively. Sulfamethoxazole works by inhibiting bacterial dihydropteroate synthase, an enzyme critical for folate synthesis, thereby disrupting nucleic acid synthesis in bacteria. It is often used in combination with trimethoprim to enhance its antibacterial efficacy. The compound is stable under normal conditions but may degrade under extreme pH or temperature. Safety data indicates that it can cause allergic reactions in some individuals, and its use should be monitored for potential side effects.
Formula:C13H14N2O2S
InChI:InChI=1S/C13H14N2O2S/c1-10-7-8-11(14)9-13(10)18(16,17)15-12-5-3-2-4-6-12/h2-9,15H,14H2,1H3
InChI key:InChIKey=HCAKHJQTCPZXPR-UHFFFAOYSA-N
SMILES:S(NC1=CC=CC=C1)(=O)(=O)C2=C(C)C=CC(N)=C2
Synonyms:- 5-Amino-o-toluenesulfonanilide
- 5-Amino-2-methyl-N-phenylbenzenesulfonamide
- Benzenesulfonamide, 5-amino-2-methyl-N-phenyl-
- 5-Amino-2-toluenesulfonanilide
- o-Toluenesulfonanilide, 5-amino-
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