Sulfacytine (CHEM016881)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:46:18 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016881
Identification
Common NameSulfacytine
ClassSmall Molecule
DescriptionSulfacytine 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.
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
RenoquidKegg
SulphacytineGenerator
1-Ethyl N4-sulfanilylcytosinHMDB
1-Ethyl-N-sulfanilylcytosineHMDB
N-Sulfanilyl-L-ethylcytosineHMDB
N(1)-(1-Ethyl-1,2-dihydro-2-oxo-4-pyrimidinyl)sulfanilamideHMDB
Chemical FormulaC12H14N4O3S
Average Molecular Mass294.330 g/mol
Monoisotopic Mass294.079 g/mol
CAS Registry Number17784-12-2
IUPAC Name4-amino-N-(1-ethyl-2-oxo-1,2-dihydropyrimidin-4-yl)benzene-1-sulfonamide
Traditional Namesulfacytine
SMILESCCN1C=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC1=O
InChI IdentifierInChI=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)
InChI KeySIBQAECNSSQUOD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentAminobenzenesulfonamides
Alternative Parents
Substituents
  • Aminobenzenesulfonamide
  • Benzenesulfonyl group
  • Aniline or substituted anilines
  • Pyrimidone
  • Hydropyrimidine
  • Pyrimidine
  • Organosulfonic acid amide
  • Imidolactam
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP0.51ALOGPS
logP0.055ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)10.55ChemAxon
pKa (Strongest Basic)2.17ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area104.86 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity75.49 m³·mol⁻¹ChemAxon
Polarizability29.43 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0699-5970000000-fcf781e9c8d92fac41feSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0490000000-f5ef4a3fc969278d52f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-1930000000-cca50de9df755740762cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-0e0f88d63239781bb3ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0190000000-5678559deb4df7cd70e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zml-1590000000-f8b5e6818df98f145ac8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bf-9710000000-fe4bdffade8dc1239d0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052b-0790000000-858e661c23fea2a281efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0005-1950000000-8efb821459dc738d0bc6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9310000000-af522fa67546c379ca39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0290000000-14fefa164bb613784c58Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dm-0920000000-252f3b6dbf3bb165daceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-6900000000-bc74a22245fbb377bce2Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01298
HMDB IDHMDB0015412
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSulfacytine
Chemspider ID5131
ChEBI ID775007
PubChem Compound ID5322
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available