Sulfamethizole (CHEM016887)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:46:28 UTC
Update Date2016-11-09 01:15:29 UTC
Accession NumberCHEM016887
Identification
Common NameSulfamethizole
ClassSmall Molecule
DescriptionA sulfonamide consisting of a 1,3,4-thiadiazole nucleus with a methyl substituent at C-5 and a 4-aminobenzenesulfonamido group at C-2.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • Suspected Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
RufolChEBI
SulfamethizolChEBI
SulfamethizolumChEBI
SulfamethylthiadiazoleChEBI
SulfametizolChEBI
SulphamethazoleChEBI
SulphamethiozoleChEBI
ThiosulfilKegg
SulphamethizolGenerator
SulphamethizolumGenerator
SulphamethylthiadiazoleGenerator
SulphametizolGenerator
SulfamethazoleGenerator
SulfamethiozoleGenerator
ThiosulphilGenerator
SulphamethizoleGenerator
Urgo brand OF sulfamethizoleHMDB
FNA brand OF sulfamethizoleHMDB
FNA, sulfamethizolHMDB
Sulfamethizol fnaHMDB
Wyeth brand OF sulfamethizoleHMDB
Chemical FormulaC9H10N4O2S2
Average Molecular Mass270.331 g/mol
Monoisotopic Mass270.025 g/mol
CAS Registry Number144-82-1
IUPAC Name4-amino-N-(5-methyl-1,3,4-thiadiazol-2-yl)benzene-1-sulfonamide
Traditional Namesulfamethizole
SMILESCC1=NN=C(NS(=O)(=O)C2=CC=C(N)C=C2)S1
InChI IdentifierInChI=1S/C9H10N4O2S2/c1-6-11-12-9(16-6)13-17(14,15)8-4-2-7(10)3-5-8/h2-5H,10H2,1H3,(H,12,13)
InChI KeyVACCAVUAMIDAGB-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
  • Organosulfonic acid amide
  • Azole
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Thiadiazole
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
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 Solubility0.61 g/LALOGPS
logP0.53ALOGPS
logP0.21ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)6.71ChemAxon
pKa (Strongest Basic)1.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.97 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity66.84 m³·mol⁻¹ChemAxon
Polarizability26.26 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, Positivesplash10-0a4i-9520000000-612be3b68261ab7e44e0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0a4i-6921000000-126773aad654d2eed32dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-1900000000-d28aaee868ff14cf276cSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-2930000000-baa3fcc8543e75aae150Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-6921000000-126773aad654d2eed32dSpectrum
LC-MS/MSLC-MS/MS Spectrum - -1V, Positivesplash10-0a4i-1900000000-be6bc1fbe226f471ada1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0190000000-65b647815b272c211343Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pi0-1980000000-7fadab7f248de98fdf2fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v0r-9020000000-38dd107f4616bd2bbcf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-e6595fd414c007267574Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02t9-1490000000-e623f31f5c64f3fc4b1eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5920000000-b4846ad87d713bf15d8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0940000000-5f9fea338a3259e1358bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-4900000000-294de38d9541211580c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-c0447fdeace53d9b33efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-37863beaac79d46e4d4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-1690000000-571175f48422a730717eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2900000000-98411d72ae7ea399e430Spectrum
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 IDDB00576
HMDB IDHMDB0014715
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSulfamethizole
Chemspider ID5137
ChEBI ID9331
PubChem Compound ID5328
Kegg Compound IDC08050
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11431418
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17180970
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=20303138
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=21275251
5. Watanabe H, Hastings JW: Inhibition of bioluminescence in Photobacterium phosphoreum by sulfamethizole and its stimulation by thymine. Biochim Biophys Acta. 1990 Jun 26;1017(3):229-34.
6. Kerrn MB, Frimodt-Moller N, Espersen F: Effects of sulfamethizole and amdinocillin against Escherichia coli strains (with various susceptibilities) in an ascending urinary tract infection mouse model. Antimicrob Agents Chemother. 2003 Mar;47(3):1002-9.
7. Ratanajamit C, Skriver MV, Norgaard M, Jepsen P, Schonheyder HC, Sorensen HT: Adverse pregnancy outcome in users of sulfamethizole during pregnancy: a population-based observational study. J Antimicrob Chemother. 2003 Nov;52(5):837-41. Epub 2003 Sep 30.