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Identification
Name Sulfacytine
Accession Number DB01298
Type small molecule
Groups approved
Description

Sulfacytine is a short-acting sulfonamide. 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.

Sulfacytine is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of of dihydrofolic acid by preventing the condensation of the pteridine with 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • 1-ethyl N4-sulfanilylcytosin
  • 1-ethyl-N-sulfanilylcytosine
  • N-sulfanilyl-l-ethylcytosine
  • Sulfacitina [inn-spanish]
  • Sulfacitinum [inn-latin]
Brand names
  • Renoquid
Brand name mixtures Not Available
Categories
  • Sulfonamides
  • Anti-Infective Agents, Urinary
CAS number 17784-12-2
Weight Average: 294.33
Monoisotopic: 294.078661024
Chemical Formula C12H14N4O3S
InChI Key InChIKey=SIBQAECNSSQUOD-UHFFFAOYSA-N
InChI
InChI=1S/C12H14N4O3S/c1-2-16-8-7-11(14-12(16)17)15-20(18,19)10-5-3-9(13)4-6-10/h3-8H,2,13H2,1H3,(H,14,15,17)
Plain Text
IUPAC Name
4-amino-N-(1-ethyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzene-1-sulfonamide
SMILES
CCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzenesulfonamides
  • Sulfanilamides
Substructures
  • Sulfonyls
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Benzenesulfonamides
  • Pyrimidines and Derivatives
  • Heterocyclic compounds
  • Aromatic compounds
  • Sulfanilamides
  • Sulfonamides
  • Cyanamides
  • Anilines
Pharmacology
Indication Used orally in the treatment of acute urinary tract infections.
Pharmacodynamics Sulfacytine is a short-acting sulfonamide. 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 Sulfacytine is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of of dihydrofolic acid by preventing the condensation of the pteridine with 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 Well absorbed following oral administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Bacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Glenwood inc
Packagers Not Available
Dosage forms
Form Route Strength
Tablet Oral
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 166.5 oC
Experimental Properties
Property Value Source
water solubility 1.75 mg/mL at 37 oC [MERCK INDEX (1996); pH 5] PhysProp
Predicted Properties
Property Value Source
water solubility 4.68e-01 g/l ALOGPS
logP 0.51 ALOGPS
logP 0.05 ChemAxon Molconvert
logS -2.80 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 2 ChemAxon Molconvert
polar surface area 104.86 ChemAxon Molconvert
rotatable bond count 3 ChemAxon Molconvert
refractivity 75.49 ChemAxon Molconvert
polarizability 29.43 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
PubChem Compound 5322 Link_out
PubChem Substance 46505483 Link_out
ChemSpider 5131 Link_out
Therapeutic Targets Database DAP001201 Link_out
PharmGKB PA451538 Link_out
Drug Product Database 0 Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Dihydropteroate synthase

Pharmacological action: yes
Actions: inhibitor

DHPS catalyzes the formation of the immediate precursor of folic acid. It is implicated in resistance to sulfonamide

Organism class: bacterial
UniProt ID: P0AC13 Link_out
Gene: folP
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Hughes J, Roberts LC, Coppridge AJ: Sulfacytine: a new sulfonamide. Double-blind comparison with sulfisoxazole in acute uncomplicated urinary tract infections. J Urol. 1975 Dec;114(6):912-4. Pubmed
Comments
Drug created on June 30, 2007 08:20 / Updated on November 10, 2010 13:47

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.