4-amino-N-(1-ethyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzene-1-sulfonamide

• ChemBase ID: 1150
• Molecular Formular: C12H14N4O3S
• Molecular Mass: 294.32956
• Monoisotopic Mass: 294.07866133
• SMILES: S(=O)(=O)(Nc1nc(=O)n(CC)cc1)c1ccc(N)cc1
• Canonical SMILES: CCn1ccc(nc1=O)NS(=O)(=O)c1ccc(cc1)N
• InChI: InChI=1S/C12H14N4O3S/c1-2-16-8-7-11(14-12(16)17)15-20(18,19)10-5-3-9(13)4-6-10/h3-8H,2,13H2,1H3,(H,14,15,17)
• InChIKey: SIBQAECNSSQUOD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-N-(1-ethyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzene-1-sulfonamide
• IUPAC Traditional name: sulfacytine
• Brand Name: Renoquid
• Synonyms: 1-ethyl N4-sulfanilylcytosin; 1-ethyl-N-sulfanilylcytosine; N-sulfanilyl-l-ethylcytosine; Sulfacitina [inn-spanish]; Sulfacitinum [inn-latin]; Sulfacytine

Database IDs

• CAS Number: 17784-12-2
• PubChem SID: 160964613; 46505483
• PubChem CID: 5322

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.5525875
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.054794375
• LogD (pH = 7.4): 0.05472528
• Log P: 0.054998476
• Molar Refractivity: 75.488 cm^3
• Polarizability: 28.825743 Å^3
• Polar Surface Area: 104.86 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.51
• LOG S: -2.8
• Solubility (Water): 4.68e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1.75 mg/mL at 37 oC [MERCK INDEX (1996); pH 5]

DETAILS

DrugBank - DB01298

• Drug Groups: approved
• Description: Sulfacytine is a short-acting sulfonamide. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections.; ; Sulfacytine is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
• Indication: Used orally in the treatment of acute urinary tract infections.
• Pharmacology: Sulfacytine is a short-acting sulfonamide. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.
• Affected Organisms: Bacteria
• Absorption: Well absorbed following oral administration.