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Identification
NameSulfoxone
Accession NumberDB01145  (APRD00704)
TypeSmall Molecule
GroupsApproved
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.

Structure
Thumb
Synonyms
SynonymLanguageCode
SulfoxoneNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Sulfoxone Sodium
Thumb
  • InChI Key: AZBNFLZFSZDPQF-UHFFFAOYSA-L
  • Monoisotopic Mass: 447.98093761
  • Average Mass: 448.445
DBSALT000408
Categories
CAS number144-75-2
WeightAverage: 404.482
Monoisotopic: 404.017048324
Chemical FormulaC14H16N2O6S3
InChI KeyNEDPPCHNEOMTJV-UHFFFAOYSA-N
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)
IUPAC Name
[(4-{4-[(sulfinomethyl)amino]benzenesulfonyl}phenyl)amino]methanesulfinic acid
SMILES
OS(=O)CNC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(NCS(O)=O)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylalkylamines. These are organic amines where the amine group is secondary and linked on one end to a phenyl group and on the other end, to an alkyl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassAralkylamines
Direct ParentPhenylalkylamines
Alternative Parents
Substituents
  • Phenylalkylamine
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Monocyclic benzene moiety
  • Sulfonyl
  • Sulfone
  • Sulfinic acid
  • Alkanesulfinic acid
  • Alkanesulfinic acid or derivatives
  • Sulfinic acid derivative
  • Secondary amine
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the treatment of leprosy and dermatitis herpetiformis
PharmacodynamicsSulfoxone 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.
Mechanism of actionSulfoxone 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.
AbsorptionRapidly absorbed.
Volume of distributionNot Available
Protein binding69%
Metabolism

Hepatic.

Route of eliminationNot Available
Half life3-8 hours
ClearanceNot Available
ToxicityOral, rat LD50: 7000 mg/kg
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9883
Blood Brain Barrier+0.7283
Caco-2 permeable-0.6186
P-glycoprotein substrateNon-substrate0.724
P-glycoprotein inhibitor INon-inhibitor0.8534
P-glycoprotein inhibitor IINon-inhibitor0.934
Renal organic cation transporterNon-inhibitor0.8985
CYP450 2C9 substrateNon-substrate0.7599
CYP450 2D6 substrateNon-substrate0.7661
CYP450 3A4 substrateNon-substrate0.6898
CYP450 1A2 substrateNon-inhibitor0.8389
CYP450 2C9 substrateNon-inhibitor0.6923
CYP450 2D6 substrateNon-inhibitor0.8693
CYP450 2C19 substrateNon-inhibitor0.64
CYP450 3A4 substrateNon-inhibitor0.7928
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.606
Ames testNon AMES toxic0.7668
CarcinogenicityCarcinogens 0.707
BiodegradationNot ready biodegradable0.9742
Rat acute toxicity2.1606 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9366
hERG inhibition (predictor II)Non-inhibitor0.7591
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP-2.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.63 mg/mLALOGPS
logP1.38ALOGPS
logP-1ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)-1.5ChemAxon
pKa (Strongest Basic)-0.056ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.8 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity96.95 m3·mol-1ChemAxon
Polarizability38.81 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS Codes
  • 8:12:20
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (36.6 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Dihydropteroate synthetase

Kind: protein

Organism: Plasmodium falciparum

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Dihydropteroate synthetase Q27738 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Katz SI: “Sulfoxone (Diasone) sodium for dermatitis herpetiformis” by Cornbleet, December 1951. Commentary: Sulfoxone (Diasone) in the treatment of dermatitis herpetiformis. Arch Dermatol. 1982 Oct;118(10):805-12. Pubmed
  4. Takahashi T: [Mutations of drug target molecules in Pneumocystis jirovecii isolates and future investigations] Nippon Ishinkin Gakkai Zasshi. 2009;50(2):67-73. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13