N-(4-aminobenzenesulfonyl)acetamide hydrate sodium

• ChemBase ID: 155424
• Molecular Formular: C8H12N2NaO4S
• Molecular Mass: 255.24665
• Monoisotopic Mass: 255.04154716
• SMILES: CC(=O)NS(=O)(=O)c1ccc(cc1)N.O.[Na]
• Canonical SMILES: CC(=O)NS(=O)(=O)c1ccc(cc1)N.O.[Na]
• InChI: InChI=1S/C8H10N2O3S.Na.H2O/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8;;/h2-5H,9H2,1H3,(H,10,11);;1H2
• InChIKey: UPEPDWDCUMJQBS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-aminobenzenesulfonyl)acetamide hydrate sodium
• IUPAC Traditional name: sulfacetamide hydrate sodium
• Synonyms: N-(p-Aminobenzenesulfonyl)acetamide; Sulfacetamide sodium salt

Database IDs

• CAS Number: 6209-17-2
• MDL Number: MFCD00007885
• PubChem SID: 162249562; 24899806
• PubChem CID: 16219986

CALCULATED PROPERTIES

• Acid pKa: 4.2999835
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.0395306
• LogD (pH = 7.4): -1.2013199
• Log P: -0.26104107
• Molar Refractivity: 52.4822 cm^3
• Polarizability: 20.56703 Å^3
• Polar Surface Area: 89.26 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Linear Formula: C8H9N2O3SNa

DETAILS

Sigma Aldrich - S8647

Application
Sulfacetamide is an antibiotic that is used to treat skin infections and urinary tract infections1. Sulfacetamide is used to study the treatment of acne and seborrheic dermatitis. It is used to study neonatal chlamydial conjunctivitis and meningococcal conjunctivitis.
Biochem/physiol Actions
Sulfacetamide is a sulfonamide antibiotic that blocks the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase. Sulfacetamide is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), which is required for bacterial synthesis of folic acid1. It is active against Gram positive bacteria, Gram negative bacteria and Chlamydia. Mode of resistance is via the alteration of dihydropteroate synthase or alternative pathway for folic acid synthesis.