DrugBank: Sulfoxone (DB01145)

targets (1)

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Adesulfone Sodium
Aldesulfone Sodium
Sodium Aldesulphone
Sodium Sulfoxone
Sulfoxone Sodium

Salts

Not Available

Brand names

Name	Company
Aldapsone
Diamidin
Diason
Diasone
Diasone Sodium
Diasone Sodium Enterab
Diazon
Novotrone

Brand mixtures

Not Available

Categories

Anti-Infectives
Anti-Bacterial Agents
Sulfonamides

CAS number

144-75-2

Weight

Average: 404.482
Monoisotopic: 404.017048324

Chemical Formula

C₁₄H₁₆N₂O₆S₃

InChI Key

InChIKey=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)

Plain Text

IUPAC Name

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

SMILES

OS(=O)CNC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(NCS(O)=O)C=C1

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Benzene and Derivatives
Anilines

Substructures

Hydroxy Compounds
Sulfonyls
Benzene and Derivatives
Sulfinic Acids and Derivatives
Sulfones
Aromatic compounds
Anilines
Sulfoxides

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.

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

Pharmacoeconomics

Manufacturers

Abbott laboratories pharmaceutical products div

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
logP	-2.8	Not Available

Predicted Properties

Property	Value	Source
water solubility	2.63e+00 g/l	ALOGPS
logP	1.38	ALOGPS
logP	-1	ChemAxon
logS	-2.2	ALOGPS
pKa (strongest acidic)	-1.5	ChemAxon
pKa (strongest basic)	-0.056	ChemAxon
physiological charge	-2	ChemAxon
hydrogen acceptor count	8	ChemAxon
hydrogen donor count	4	ChemAxon
polar surface area	132.8	ChemAxon
rotatable bond count	8	ChemAxon
refractivity	96.95	ChemAxon
polarizability	38.81	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
PubChem Compound	5351
PubChem Substance	46507392
ChemSpider	5158
Therapeutic Targets Database	DAP001192
PharmGKB	PA164776911

ATC Codes

Not Available

AHFS Codes

8:12:20

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (36.6 KB)

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Dihydropteroate synthetase Pharmacological action: yes Actions: inhibitor Organism class: parasitic UniProt ID: Q27738 Protein Sequence: FASTA Gene Sequence: FASTA References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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 Takahashi T: [Mutations of drug target molecules in Pneumocystis jirovecii isolates and future investigations] Nippon Ishinkin Gakkai Zasshi. 2009;50(2):67-73. Pubmed

Targets

1. Dihydropteroate synthetase

Pharmacological action: yes
Actions: inhibitor
Organism class: parasitic
UniProt ID: Q27738 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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
Takahashi T: [Mutations of drug target molecules in Pneumocystis jirovecii isolates and future investigations] Nippon Ishinkin Gakkai Zasshi. 2009;50(2):67-73. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19