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Version 2.5
Creation Date 2007-06-30 14:20:24
Update Date 2009-02-19 16:03:47
Primary Accession Number DB01298
Secondary Accession Number Not Available
Name Sulfacytine
Drug Type
  • Approved
  • Small Molecule
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.
Synonyms
  1. 1-ethyl N4-sulfanilylcytosin
  2. 1-ethyl-N-sulfanilylcytosine
  3. N-sulfanilyl-l-ethylcytosine
  4. Sulfacitina [inn-spanish]
  5. Sulfacitinum [inn-latin]
Brand Names
  1. Renoquid
Brand Mixtures Not Available
Chemical IUPAC Name 4-amino-N-(1-ethyl-2-oxopyrimidin-4-yl)benzenesulfonamide
Chemical Formula C12H14N4O3S
Chemical Structure Structure
CAS Registry Number 17784-12-2
InChI Identifier InChI=1/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)/f/h15H
InChI Key SIBQAECNSSQUOD-YAQRNVERCY
KEGG Drug Not Available
KEGG Compound Not Available
PubChem Compound 5322 Link Image
PubChem Substance 10349273 Link Image
ChEBI ID Not Available
PharmGKB ID PA451538 Link Image
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) Not Available
Synthesis Reference Not Available
Average Molecular Weight 294.3300
Monoisotopic Molecular Weight 294.0787
State Solid
Melting Point 166.5 oC
Experimental Water Solubility 1.75 mg/mL at 37 oC [MERCK INDEX (1996); pH 5] Source: PhysProp
Predicted Water Solubility 4.68e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP 0.51 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.80 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 CCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O
Canonical SMILES CCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O
Drug Category
  • Anti-Infective Agents, Urinary
  • Sulfonamides
ATC Codes Not Available
AHFS Codes Not Available
Indication Used orally in the treatment of acute urinary tract infections.
Pharmacology 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.
Toxicity Not Available
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms
Form Route
Tablet Oral
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References Not Available
Organisms Affected
  • Bacteria
Targets
  1. Dihydropteroate synthase
Drug Target 1 [top]
Target 1 ID 891
Target 1 Name Dihydropteroate synthase
Target 1 Synonyms
  1. DHPS
  2. Dihydropteroate pyrophosphorylase
  3. EC 2.5.1.15
Target 1 Gene Name folP
Target 1 Protein Sequence >Dihydropteroate synthase 
MKLFAQGTSLDLSHPHVMGILNVTPDSFSDGGTHNSLIDAVKHANLMINAGATIIDVGGE
STRPGAAEVSVEEELQRVIPVVEAIAQRFEVWISVDTSKPEVIRESAKVGAHIINDIRSL
SEPGALEAAAETGLPVCLMHMQGNPKTMQEAPKYDDVFAEVNRYFIEQIARCEQAGIAKE
KLLLDPGFGFGKNLSHNYSLLARLAEFHHFNLPLLVGMSRKSMIGQLLNVGPSERLSGSL
ACAVIAAMQGAHIIRVHDVKETVEAMRVVEATLSAKENKRYE
Target 1 Number of Residues 286
Target 1 Molecular Weight 30616
Target 1 Theoretical pI 5.95
Target 1 GO Classification
Function
transferase activity, transferring alkyl or aryl (other than methyl) groups
catalytic activity
transferase activity
transferase activity, transferring alkyl or aryl (other than methyl) groups
dihydropteroate synthase activity
Process
physiological process
metabolism
cellular metabolism
aromatic compound metabolism
folic acid and derivative metabolism
folic acid and derivative biosynthesis
Component
Not Available
Target 1 General Function Coenzyme transport and metabolism
Target 1 Specific Function DHPS catalyzes the formation of the immediate precursor of folic acid. It is implicated in resistance to sulfonamide
Target 1 Pathways
Name SMPDB Link KEGG Link
Folate biosynthesis map00790 Link Image
Target 1 Reactions
  • (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate + 4-aminobenzoate = diphosphate + 7,8-dihydropteroate
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 41273 Link Image
Target 1 UniProtKB/Swiss-Prot ID P0AC13 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name DHPS_ECOLI Link Image
Target 1 PDB ID 1AJZ Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location Not Available
Target 1 Gene Sequence >849 bp 
ATGAAACTTTTTGCCCAGGGTACTTCACTGGACCTTAGCCATCCTCACGTAATGGGGATC
CTCAACGTCACGCCTGATTCCTTTTCGGATGGTGGCACGCATAACTCGCTGATAGATGCG
GTGAAACATGCGAATCTGATGATCAACGCTGGCGCGACGATCATTGACGTTGGTGGCGAG
TCCACGCGCCCAGGGGCGGCGGAAGTTAGCGTTGAAGAAGAGTTGCAACGTGTTATTCCT
GTGGTTGAGGCAATTGCTCAACGCTTCGAAGTCTGGATCTCAGTCGATACATCCAAACCA
GAAGTCATCCGTGAGTCAGCGAAAGTTGGCGCTCACATTATTAATGATATCCGCTCCCTT
TCCGAACCTGGCGCTCTGGAGGCGGCTGCAGAAACCGGTTTACCGGTTTGTCTGATGCAT
ATGCAGGGAAATCCAAAAACCATGCAGGAAGCTCCGAAGTATGACGATGTCTTTGCAGAA
GTGAATCGCTACTTTATTGAGCAAATAGCACGTTGCGAGCAGGCGGGTATCGCAAAAGAG
AAATTGTTGCTCGACCCCGGATTCGGTTTCGGTAAAAATCTCTCCCATAACTATTCATTA
CTGGCGCGCCTGGCTGAATTTCACCATTTCAACCTGCCGCTGTTGGTGGGTATGTCACGA
AAATCGATGATTGGGCAGCTGCTGAACGTGGGGCCGTCCGAGCGCCTGAGCGGTAGTCTG
GCCTGTGCGGTCATTGCCGCAATGCAAGGCGCGCACATCATTCGTGTTCATGACGTCAAA
GAAACCGTAGAAGCGATGCGGGTGGTGGAAGCCACTCTGTCTGCAAAGGAAAACAAACGC
TATGAGTAA
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 SNPJam Report Link Image
Target 1 General References
  1. Dallas WS, Gowen JE, Ray PH, Cox MJ, Dev IK: Cloning, sequencing, and enhanced expression of the dihydropteroate synthase gene of Escherichia coli MC4100. J Bacteriol. 1992 Sep;174(18):5961-70. [PubMed Link Image]
  2. Talarico TL, Dev IK, Dallas WS, Ferone R, Ray PH: Purification and partial characterization of 7,8-dihydro-6-hydroxymethylpterin-pyrophosphokinase and 7,8-dihydropteroate synthase from Escherichia coli MC4100. J Bacteriol. 1991 Nov;173(21):7029-32. [PubMed Link Image]
  3. Swedberg G, Fermer C, Skold O: Point mutations in the dihydropteroate synthase gene causing sulfonamide resistance. Adv Exp Med Biol. 1993;338:555-8. [PubMed Link Image]
  4. Achari A, Somers DO, Champness JN, Bryant PK, Rosemond J, Stammers DK: Crystal structure of the anti-bacterial sulfonamide drug target dihydropteroate synthase. Nat Struct Biol. 1997 Jun;4(6):490-7. [PubMed Link Image]
  5. Blattner FR, Plunkett G 3rd, Bloch CA, Perna NT, Burland V, Riley M, Collado-Vides J, Glasner JD, Rode CK, Mayhew GF, Gregor J, Davis NW, Kirkpatrick HA, Goeden MA, Rose DJ, Mau B, Shao Y: The complete genome sequence of Escherichia coli K-12. Science. 1997 Sep 5;277(5331):1453-74. [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.