Basic information
- CAS
144-75-2- Standard SMILES
O=S(O)CNc1ccc(S(=O)(=O)c2ccc(NCS(=O)O)cc2)cc1- InChIKey
NEDPPCHNEOMTJV-UHFFFAOYSA-N- Molecular formula
- C14H16N2O6S3
- Average molar mass
- 404.5 g/mol
- Monoisotopic mass
- 404.01704923
Overview
Aldesulfone is a sulfonamide.
Names & identifiers
- Preferred name
- Sulfoxone
- IUPAC
- [4-[4-(sulfinomethylamino)phenyl]sulfonylanilino]methanesulfinic acid
- English name
- sulfoxone
- Molecular formula
- C14H16N2O6S3
- Molecular weight
- 404.48
Names & synonyms
Show more names
Database identifiers
- CAS
144-75-2、144-76-3- PubChem CID
- 5351
- DTXSID
DTXSID80162594- ChEMBL
CHEMBL1570- ChEBI
CHEBI:135651- UNII
- 0G3C18OH4D
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 180 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 8
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 520
Experimental & physicochemical properties
Physicochemical properties
- Boiling point
- 857.3 · 857.3±75.0 °C(Predicted)
- Density
- 1.753 · 1.753±0.06 g/cm3(Predicted)
- pka
- 2.58 · 2.58±0.10(Predicted)
- FDA UNII
- 0 G3C18OH4D · 0G3C18OH4D
Chemistry & industry
Pharmacology
Pharmacodynamics
Sulfoxone is a sulfonamide antibiotic. 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 <i>p</i>-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.
Mechanism of Action
Sulfoxone is a competitive inhibitor of bacterial enzyme dihydropteroate synthetase. The normal substrate for the enzyme, para-aminobenzoic acid (PABA) cannot bind as usual. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Suppliers1 total
Additional notes
DefinitionChEBI: Aldesulfone is a sulfonamide.
Related reactions
Compound notes
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