Identification

Name
Sulfoxone
Accession Number
DB01145  (APRD00704)
Type
Small Molecule
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.

Structure
Thumb
Synonyms
  • Aldesulfone
  • Aldesulphone
Product Ingredients
IngredientUNIICASInChI Key
Sulfoxone sodium57OWB0Q221144-75-2AZBNFLZFSZDPQF-UHFFFAOYSA-L
Categories
UNII
0G3C18OH4D
CAS number
144-76-3
Weight
Average: 404.482
Monoisotopic: 404.017048324
Chemical Formula
C14H16N2O6S3
InChI Key
NEDPPCHNEOMTJV-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

Pharmacology

Indication

For the treatment of leprosy and dermatitis herpetiformis

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 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 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.

TargetActionsOrganism
ADihydropteroate synthetase
inhibitor
Plasmodium falciparum
Absorption

Rapidly absorbed.

Volume of distribution
Not Available
Protein binding

69%

Metabolism

Hepatic.

Route of elimination
Not Available
Half life

3-8 hours

Clearance
Not Available
Toxicity

Oral, rat LD50: 7000 mg/kg

Affected organisms
  • Enteric bacteria and other eubacteria
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015276
PubChem Compound
5351
PubChem Substance
46507392
ChemSpider
5158
ChEBI
135651
ChEMBL
CHEMBL1570
Therapeutic Targets Database
DAP001192
PharmGKB
PA164776911
Wikipedia
Sulfoxone
ATC Codes
J04BA03 — Aldesulfone sodium
MSDS
Download (36.6 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 inhibitorNon-inhibitor0.6923
CYP450 2D6 inhibitorNon-inhibitor0.8693
CYP450 2C19 inhibitorNon-inhibitor0.64
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonyl compounds
Direct Parent
Benzenesulfonyl compounds
Alternative Parents
Phenylalkylamines / Secondary alkylarylamines / Sulfones / Sulfinic acids / Alkanesulfinic acids / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Benzenesulfonyl group / Phenylalkylamine / Secondary aliphatic/aromatic amine / Sulfinic acid / Sulfone / Sulfonyl / Alkanesulfinic acid / Alkanesulfinic acid or derivatives / Sulfinic acid derivative / Secondary amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Plasmodium falciparum
Pharmacological action
Yes
Actions
Inhibitor
General Function
Dihydropteroate synthase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q27738
Uniprot Name
Dihydropteroate synthetase
Molecular Weight
43370.845 Da
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:17139284]
  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:17016423]
  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:6753759]
  4. Takahashi T: [Mutations of drug target molecules in Pneumocystis jirovecii isolates and future investigations]. Nihon Ishinkin Gakkai Zasshi. 2009;50(2):67-73. [PubMed:19430180]

Drug created on June 13, 2005 07:24 / Updated on October 01, 2018 16:26