[(4-{4-[(sulfinomethyl)amino]benzenesulfonyl}phenyl)amino]methanesulfinic acid

• ChemBase ID: 1016
• Molecular Formular: C14H16N2O6S3
• Molecular Mass: 404.48164
• Monoisotopic Mass: 404.01704924
• SMILES: S(=O)(=O)(c1ccc(NCS(=O)O)cc1)c1ccc(NCS(=O)O)cc1
• Canonical SMILES: OS(=O)CNc1ccc(cc1)S(=O)(=O)c1ccc(cc1)NCS(=O)O
• InChI: InChI=1S/C14H16N2O6S3/c17-23(18)9-15-11-1-5-13(6-2-11)25(21,22)14-7-3-12(4-8-14)16-10-24(19)20/h1-8,15-16H,9-10H2,(H,17,18)(H,19,20)
• InChIKey: NEDPPCHNEOMTJV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(4-{4-[(sulfinomethyl)amino]benzenesulfonyl}phenyl)amino]methanesulfinic acid
• IUPAC Traditional name: [(4-{4-[(sulfinomethyl)amino]benzenesulfonyl}phenyl)amino]methanesulfinic acid
• Brand Name: Aldapsone; DDF; Diamidin; Diason; Diasone; Diasone Sodium; Diasone Sodium Enterab; Diazon; Novotrone
• Synonyms: Sulfoxone Sodium; Sodium Sulfoxone; Sodium Aldesulphone; Aldesulfone Sodium; Adesulfone Sodium; Sulfoxone

Database IDs

• CAS Number: 144-75-2
• PubChem SID: 160964479; 46507392
• PubChem CID: 5351

CALCULATED PROPERTIES

JChem

• LogD (pH = 7.4): -3.257101
• Log P: -1.0329583
• Molar Refractivity: 96.9524 cm^3
• Polarizability: 38.591267 Å^3
• Polar Surface Area: 132.8 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true
• Acid pKa: -1.4567201
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.2571752

ALOGPS 2.1

• Log P: 1.38
• LOG S: -2.19
• Solubility (Water): 2.63e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -2.8

DETAILS

DrugBank - DB01145

• Drug Groups: approved
• Description: Sulfoxone is a water-soluble sulfone used as an antileprosy drug. It has been used with limited success in the treatment of dermatitis herpetiformis.
• Indication: For the treatment of leprosy and dermatitis herpetiformis
• Pharmacology: 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 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.
• Toxicity: Oral, rat LD₅₀: 7000 mg/kg
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Hepatic.
• Absorption: Rapidly absorbed.
• Half Life: 3-8 hours
• Protein Binding: 69%