Sulfamethizole (CED0009417)

Record Information
Version1.0
Creation Date2016-05-22 03:46:28 UTC
Update Date2026-08-25 07:47:36 UTC
Accession NumberCHEM016887
Identification
Common NameSulfamethizole
ClassSmall Molecule
Description
Sulfamethizole is an organic compound with the chemical formula C9H10N4O2S2 and an average molecular weight of 270.33 g/mol. Sulfamethizole belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. In terms of biological activity, it is recorded as an inhibitor of the protein target dihydropteroate synthase (folP). The compound is found in or released from 23 recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is associated with antiinfectives, chemotherapy, gynecologicals, irrigating solutions, and sulfonamides and trimethoprim. It is also linked to food, food processing, and cookware, specifically in meat processing, food preservation, and the preparation of wort. Other recorded sources include household cleaning and consumer products, such as soap detergents, perfumes within detergents and soaps, and tobacco smoke filters. Additionally, it is found in building and construction materials, specifically roofs, as well as electrical and electronic equipment, including communication cables or conductors, antennas, coils, cores yokes or armatures, and conductors or conductive bodies characterised by the conductive materials. Recorded exposure routes for this compound include inhalation and oral ingestion.
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-9520000000-612be3b68261ab7e44e0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-6921000000-126773aad654d2eed32dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1900000000-d28aaee868ff14cf276cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2930000000-baa3fcc8543e75aae150Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-6921000000-126773aad654d2eed32dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1900000000-be6bc1fbe226f471ada1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fk9-0190000000-65b647815b272c211343Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pi0-1980000000-7fadab7f248de98fdf2fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0v0r-9020000000-38dd107f4616bd2bbcf5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0090000000-e6595fd414c007267574Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02t9-1490000000-e623f31f5c64f3fc4b1eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-5920000000-b4846ad87d713bf15d8aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-0940000000-5f9fea338a3259e1358bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-4900000000-294de38d9541211580c5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-9000000000-c0447fdeace53d9b33efNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0090000000-37863beaac79d46e4d4dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-066r-1690000000-571175f48422a730717eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-2900000000-98411d72ae7ea399e430Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2351.0Log mg/kg[1300:4200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
279Irrigating solutionsHealthcare, pharmaceuticals & veterinary productsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
307ChemotherapeuticsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
342Sulfonamides and trimethoprimHealthcare, pharmaceuticals & veterinary productsNot Available
395AntiinfectivesHealthcare, pharmaceuticals & veterinary productsNot Available
499RoofsBuilding & ConstructionNot Available
506AntennasElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)8.17417
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)8.95266
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)9.49761
Click to view 3D structureCarbonic anhydrase 4Q95323Bos taurusPredicted (SEA)3.89246
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)4.5931
Click to view 3D structureCarbonic anhydraseO24855Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)Predicted (SEA)1.32344
Click to view 3D structureAGAP002992-PAQ5TU56Anopheles gambiaePredicted (SEA)0.467095
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)18.9952
Click to view 3D structureAstrosclerin-3A6YCJ1Astrosclera willeyanaPredicted (SEA)1.94623
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)6.46149
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)8.25202
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)6.77288
Click to view 3D structureCarbonate dehydrataseB2V8E3Sulfurihydrogenibium sp. (strain YO3AOP1)Predicted (SEA)1.94623
Click to view 3D structureCarbonic anhydraseQ6FTL6Candida glabrata CBS 138Predicted (SEA)3.73676
Click to view 3D structureAlpha carbonic anhydraseB5SU02Stylophora pistillataPredicted (SEA)2.10193
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)2.64687
Click to view 3D structureCarbonic anhydrase, alpha familyQ31FD6Thiomicrospira crunogenaPredicted (SEA)1.94623
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)3.42537
Click to view 3D structureCarbonic anhydraseC0IX24Stylophora pistillataPredicted (SEA)2.10193
Click to view 3D structureBeta-carbonic anhydrase 1P9WPJ7Mycobacterium tuberculosisPredicted (SEA)5.3716
Click to view 3D structureCarbonic anhydrase 13Q9D6N1Mus musculusPredicted (SEA)3.50322
Click to view 3D structureCarbonic anhydraseP53615Saccharomyces cerevisiae S288cPredicted (SEA)1.86838
Click to view 3D structureCarbonic anhydrase 2P9WPJ9Mycobacterium tuberculosisPredicted (SEA)0.311397
Click to view 3D structureCarbonic anhydrase 15Q99N23Mus musculusPredicted (SEA)7.08428
Click to view 3D structureDelta carbonic anhydraseQ5U9J1Conticribra weissflogiiPredicted (SEA)4.20386
Concentrations
Not Available
External Links
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.