Sulfoxone

HCID 5351

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

sulfoxoneAldesulfoneAldesulphone144-76-3aldesulfon sodium0G3C18OH4DDTXSID80162594Methanesulfinic acid, (sulfonylbis(4,1-phenyleneimino))bis-((4-((4-((sulfinomethyl)amino)benzene)sulfonyl)phenyl)amino)methanesulfinic acid{[4-({4-[(sulfinomethyl)amino]benzene}sulfonyl)phenyl]amino}methanesulfinic acidRefChem:889709DTXCID50196725
Show more names
Sulfoxone (Aldesulfone)NEDPPCHNEOMTJV-UHFFFAOYSA-NMethanesulfinic acid, 1,1'-[sulfonylbis(4,1-phenyleneimino)]bis-[[4-[4-(sulfinomethylamino)phenyl]sulfonylphenyl]amino]methanesulfinic acid
1,1'-(Sulfonylbis(4,1-phenyleneimino))bis(methanesulfinic acid)Sodium sulfoxoneSodium aldesulphoneDiasoneAldesulfon[4-[4-(sulfinomethylamino)phenyl]sulfonylanilino]methanesulfinic acid((sulfonylbis(4,1-phenylene))bis(azanediyl))dimethanesulfinic acidUNII-0G3C18OH4D

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

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP-2.8
Solubility2.63e+00 g/L
Physical DescriptionSolid

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

Protein Binding69%
Pharmacodynamics · 1 item

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 · 1 item

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.

Biological Half-Life3-8 hours
Metabolism/MetabolitesHepatic.
Absorption, Distribution and ExcretionRapidly absorbed.

Suppliers1 total

湖北扬信医药科技有限公司0714-3999001 19171453112 · [email protected]

Additional notes

DefinitionChEBI: Aldesulfone is a sulfonamide.

Related reactions

2 records

Compound notes

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