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Showing drug card for Sulfoxone (DB01145)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:24
Primary Accession Number DB01145
Secondary Accession Number
  • APRD00704
Name Sulfoxone
Drug Type
  • Approved
  • Small Molecule
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.
Synonyms
  1. Adesulfone Sodium
  2. Aldesulfone Sodium
  3. Sodium Aldesulphone
  4. Sodium Sulfoxone
  5. Sulfoxone Sodium
Brand Names
  1. Aldapsone
  2. DDF
  3. Diamidin
  4. Diason
  5. Diasone
  6. Diasone Sodium
  7. Diasone Sodium Enterab
  8. Diazon
  9. Novotrone
Brand Mixtures Not Available
Chemical IUPAC Name [[4-[4-(sulfinomethylamino)phenyl]sulfonylphenyl]amino]methanesulfinic acid
Chemical Formula C14H16N2O6S3
Chemical Structure Structure
CAS Registry Number 144-75-2
InChI Identifier InChI=1/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)/f/h17,19H
InChI Key NEDPPCHNEOMTJV-FQFUPTBWCJ
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 5351 Link Image
PubChem Substance 152108 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link Not Available
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 404.4820
Monoisotopic Molecular Weight 404.0170
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 2.63e+00 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity -2.8 Source: PhysProp
Predicted LogP 1.38 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.19 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES O[S@](=O)CNC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(NC[S@](O)=O)C=C1
Canonical SMILES OS(=O)CNC1=CC=C(C=C1)S(=O)(=O)C1=CC=C(NCS(O)=O)C=C1
Drug Category
  • Anti-Bacterial Agents
  • Anti-Infectives
ATC Codes Not Available
AHFS Codes Not Available
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.
Mechanism of Action Sulfoxone is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.
Absorption Rapidly absorbed.
Toxicity Oral, rat LD50: 7000 mg/kg
Protein Binding 69%
Biotransformation Hepatic.
Half Life 3-8 hours
Dosage Forms Not Available
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References Not Available
Organisms Affected
  • Enteric bacteria and other eubacteria
Targets
  1. Dihydroorotate dehydrogenase homolog, mitochondrial
Drug Target 1 [top]
Target 1 ID 674
Target 1 Name Dihydroorotate dehydrogenase homolog, mitochondrial
Target 1 Synonyms
  1. DHOdehase
  2. Dihydroorotate dehydrogenase homolog, mitochondrial precursor
  3. Dihydroorotate oxidase
  4. EC 1.3.3.1
Target 1 Gene Name Not Available
Target 1 Protein Sequence >Dihydroorotate dehydrogenase homolog, mitochondrial precursor 
MISKLKPQFMFLPKKHILSYCRKDVLNLFEQKFYYTSKRKESNNMKNESLLRLINYNRYY
NKIDSNNYYNGGKILSNDRQYIYSPLCEYKKKINDISSYVSVPFKINIRNLGTSNFVNNK
KDVLDNDYIYENIKKEKSKHKKIIFLLFVSLFGLYGFFESYNPEFFLYDIFLKFCLKYID
GEICHDLFLLLGKYNILPYDTSNDSIYACTNIKHLDFINPFGVAAGFDKNGVCIDSILKL
GFSFIEIGTITPRGQTGNAKPRIFRDVESRSIINSCGFNNMGCDKVTENLILFRKRQEED
KLLSKHIVGVSIGKNKDTVNIVDDLKYCINKIGRYADYIAINVSSPNTPGLRDNQEAGKL
KNIILSVKEEIDNLEKNNIMNDESTYNEDNKIVEKKNNFNKNNSHMMKDAKDNFLWFNTT
KKKPLVFVKLAPDLNQEQKKEIADVLLETNIDGMIISNTTTQINDIKSFENKKGGVSGAK
LKDISTKFICEMYNYTNKQIPIIASGGIFSGLDALEKIEAGASVCQLYSCLVFNGMKSAV
QIKRELNHLLYQRGYYNLKEAIGRKHSKS
Target 1 Number of Residues 578
Target 1 Molecular Weight 65559
Target 1 Theoretical pI 9.44
Target 1 GO Classification
Function
oxidoreductase activity, acting on the CH-CH group of donors, oxygen as acceptor
dihydroorotate oxidase activity
catalytic activity
oxidoreductase activity
oxidoreductase activity, acting on the CH-CH group of donors
dihydroorotate dehydrogenase activity
Process
physiological process
metabolism
cellular metabolism
nucleobase, nucleoside, nucleotide and nucleic acid metabolism
nucleobase metabolism
pyrimidine base metabolism
pyrimidine base biosynthesis
'de novo' pyrimidine base biosynthesis
Component
cell
membrane
Target 1 General Function Nucleotide transport and metabolism
Target 1 Specific Function Not Available
Target 1 Pathways
Name SMPDB Link KEGG Link
Pyrimidine metabolism SMP00046 Link Image map00240 Link Image
Target 1 Reactions
  • (S)-dihydroorotate + O2 = orotate + H2O2
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 143-162
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 46362265 Link Image
Target 1 UniProtKB/Swiss-Prot ID Q08210 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name PYRD_PLAF7 Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Mitochondrion
  • mitochondrial inner membrane (Probable)
Target 1 Gene Sequence >1710 bp 
ATGATCTCTAAATTGAAACCTCAATTTATGTTTTTACCAAAGAAACATATTTTAAGTTAT
TGTAGAAAGGATGTTTTAAATTTGTTTGAACAGAAGTTTTATTATACTAGCAAACGGAAA
GAAAGTAATAATATGAAGAATGAATCTTTATTAAGATTAATTAATTATAATAGATATTAT
AATAAGATAGATTCTAATAATTATTATAATGGTGGAAAAATATTAAGTAATGATAGGCAA
TATATATATTCACCATTATGTGAATATAAAAAGAAAATAAATGATATATCATCATATGTA
TCTGTACCTTTTAAGATTAATATAAGAAATTTAGGTACTTCCAATTTTGTAAATAATAAG
AAGGATGTACTTGATAATGATTATATTTATGAAAATATTAAAAAAGAAAAATCTAAGCAT
AAAAAAATAATATTTTTATTATTTGTTTCATTATTTGGATTATATGGTTTTTTTGAATCT
TATAATCCTGAATTTTTTTTATATGATATATTTTTAAAATTCTGTTTAAAATATATTGAT
GGTGAAATATGTCATGACCTTTTTTTATTACTAGGAAAATATAATATATTACCATATGAT
ACTAGTAATGATAGTATATATGCATGTACAAATATTAAACATCTTGATTTTATAAATCCA
TTCGGTGTTGCTGCAGGATTTGATAAAAACGGTGTATGTATAGATAGCATATTAAAATTA
GGGTTTTCGTTTATCGAAATTGGTACCATAACCCCAAGGGGCCAAACGGGTAATGCAAAA
CCACGTATTTTTAGAGACGTTGAATCTAGAAGTATTATAAATTCATGTGGCTTTAATAAT
ATGGGTTGTGACAAAGTTACAGAAAATTTAATACTTTTTCGTAAAAGACAAGAAGAAGAT
AAATTGTTAAGTAAACATATTGTAGGTGTCAGTATAGGTAAGAATAAAGATACTGTTAAT
ATTGTAGATGATCTAAAATATTGTATTAATAAAATAGGAAGATACGCTGATTATATAGCT
ATTAATGTAAGCTCCCCTAATACACCTGGGTTAAGAGATAATCAAGAAGCTGGGAAGTTA
AAAAATATAATTTTAAGTGTAAAAGAAGAAATAGATAATTTAGAAAAGAATAATATTATG
AATGATGAAAGTACTTATAATGAAGATAATAAAATAGTAGAAAAAAAAAATAATTTTAAT
AAAAATAATAGTCACATGATGAAAGATGCTAAGGATAACTTCTTATGGTTTAATACAACA
AAAAAGAAGCCCTTGGTTTTTGTTAAGTTAGCTCCAGATCTTAATCAAGAACAGAAAAAA
GAAATTGCTGATGTATTACTTGAAACTAATATAGATGGTATGATTATTTCTAATACTACG
ACACAAATAAATGACATAAAAAGTTTTGAAAATAAAAAAGGAGGTGTTAGCGGAGCAAAA
CTAAAAGATATATCTACAAAATTTATATGTGAAATGTATAATTATACAAATAAACAAATA
CCCATTATTGCATCAGGAGGGATATTTAGTGGATTGGATGCTTTAGAAAAAATTGAAGCA
GGTGCTTCAGTTTGTCAATTATATTCTTGTTTGGTTTTTAATGGTATGAAATCAGCTGTA
CAAATAAAAAGAGAATTGAATCACTTGCTATATCAAAGAGGATATTACAATTTAAAGGAG
GCCATTGGCCGAAAGCATAGCAAAAGTTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs Not Available
Target 1 General References
  1. Hall N, Pain A, Berriman M, Churcher C, Harris B, Harris D, Mungall K, Bowman S, Atkin R, Baker S, Barron A, Brooks K, Buckee CO, Burrows C, Cherevach I, Chillingworth C, Chillingworth T, Christodoulou Z, Clark L, Clark R, Corton C, Cronin A, Davies R, Davis P, Dear P, Dearden F, Doggett J, Feltwell T, Goble A, Goodhead I, Gwilliam R, Hamlin N, Hance Z, Harper D, Hauser H, Hornsby T, Holroyd S, Horrocks P, Humphray S, Jagels K, James KD, Johnson D, Kerhornou A, Knights A, Konfortov B, Kyes S, Larke N, Lawson D, Lennard N, Line A, Maddison M, McLean J, Mooney P, Moule S, Murphy L, Oliver K, Ormond D, Price C, Quail MA, Rabbinowitsch E, Rajandream MA, Rutter S, Rutherford KM, Sanders M, Simmonds M, Seeger K, Sharp S, Smith R, Squares R, Squares S, Stevens K, Taylor K, Tivey A, Unwin L, Whitehead S, Woodward J, Sulston JE, Craig A, Newbold C, Barrell BG: Sequence of Plasmodium falciparum chromosomes 1, 3-9 and 13. Nature. 2002 Oct 3;419(6906):527-31. [PubMed Link Image]
  2. LeBlanc SB, Wilson CM: The dihydroorotate dehydrogenase gene homologue of Plasmodium falciparum. Mol Biochem Parasitol. 1993 Aug;60(2):349-51. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.