Sulfanilamide (CED0002125)

Record Information
Version1.0
Creation Date2016-05-19 02:40:48 UTC
Update Date2026-08-23 15:11:07 UTC
Accession NumberCHEM008209
Identification
Common NameSulfanilamide
ClassSmall Molecule
Description
Sulfanilamide is an organic compound with the formula C6H8N2O2S and an average molecular weight of 172.21 g/mol. Sulfanilamide belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. It acts as an inhibitor of the protein target dihydropteroate synthase (folP). The compound is found in or released from 39 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is associated with antibiotics, chemotherapeutics, gynecologicals, and sulfonamides and trimethoprim. It is recorded in food, food processing, and cookware sources, including food preservation, the preparation of vinegar, the preparation of wine or sparkling wine, fermentation processes for beer, and agglomerated sugar products. Household cleaning and consumer product sources include bleaching agents, cigar cigarettes, perfumes within detergents and soaps, other smoking requisites, and non electric simulated smoking devices. In electrical and electronic equipment, it is found in amplifiers, antennas, colour television systems, cores yokes or armatures, and conductors or conductive bodies characterised by the conductive materials, among 15 more. Additionally, it is found in building and construction materials such as floors and fencing. Recorded exposure routes for sulfanilamide include oral, vaginal, and inhalation.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
4-Aminobenzene sulfonic acid amideChEBI
4-AzanylbenzenesulfonamideChEBI
p-AminobenzenesulfamideChEBI
p-AminobenzenesulfonamideChEBI
Para-aminobenzenesulfonamideChEBI
Prontosil albumChEBI
SAChEBI
StreptocideChEBI
SulfamineChEBI
SulphanilamideChEBI
StreptocidKegg
AVCKegg
4-Aminobenzene sulfonate amideGenerator
4-Aminobenzene sulphonate amideGenerator
4-Aminobenzene sulphonic acid amideGenerator
4-AzanylbenzenesulphonamideGenerator
p-AminobenzenesulphamideGenerator
p-AminobenzenesulphonamideGenerator
Para-aminobenzenesulphonamideGenerator
SulphamineGenerator
p-AminobenzenesulfonylamideHMDB
p-AminobenzensulfonamideHMDB
p-AminophenylsulfonamideHMDB
p-AnilinesulfonamideHMDB
p-SulfamidoanilineHMDB
p-SulfamoylanilineHMDB
PABSHMDB
Sulfanilimidic acidHMDB
SulfonylamideHMDB
SulphonamideHMDB
Sulfanilamide cadmium saltHMDB
Sulfanilamide hydrochlorideHMDB
Sulfanilamide strontium saltHMDB
Sulfanilamide zinc saltHMDB
Sulfanilamide monohydrateHMDB
Azol polvoHMDB
Sulfanilamide magnesium saltHMDB
Sulfanilamide silver saltHMDB
Sulfanilamide sodium saltHMDB
4-AminobenzenesulfonamideHMDB
Sulfanilamide barium saltHMDB
Sulfanilamide lithium saltHMDB
Sulfanilamide sodiumHMDB
4 AminobenzenesulfonamideHMDB
Chemical FormulaC6H8N2O2S
Average Molecular Mass172.205 g/mol
Monoisotopic Mass172.031 g/mol
CAS Registry Number63-74-1
IUPAC Name4-aminobenzene-1-sulfonamide
Traditional Namesulfanilamide
SMILESNC1=CC=C(C=C1)S(N)(=O)=O
InChI IdentifierInChI=1S/C6H8N2O2S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H2,8,9,10)
InChI KeyFDDDEECHVMSUSB-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
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility10.4 g/LALOGPS
logP-0.16ALOGPS
logP-0.25ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)10.99ChemAxon
pKa (Strongest Basic)2.27ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area86.18 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.92 m³·mol⁻¹ChemAxon
Polarizability16.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0avl-9800000000-517ec40f53253fdb0135Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0avl-9800000000-517ec40f53253fdb0135Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05c6-9500000000-b4fc349159a78c29204bNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fr-0900000000-50278150b601ad9e8f07Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fr-0900000000-43cb75637a921937a7a5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uk9-5900000000-50aaf376888d903aa161Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0h93-9400000000-cf00412f8d6022da5a4eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-02h9-9100000000-d798abed368c30f832c4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00lr-9000000000-5cd62daf8fa463f7b17cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9200000000-4ef459baf708374fc2d8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9500000000-7ae6f1d0e8f165c2d844Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dl-5900000000-3c4abfe68dfb00591f77Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-9000000000-2fb9530afdc486706a7aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00fr-6900000000-32edaedbd96c87cd7c2cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-94967bc9f37175e63f3aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-1900000000-8648d1f22eea66464f5fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-25a8c2300e0eec89731eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01t9-9000000000-c1aaeae0ee3d2cf5856fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kf-9100000000-70d75d857809910b0d74Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9200000000-d5c185d9f678c2363a77Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016u-9000000000-6a84e16e85428febde6dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-016r-9000000000-d9ad76c4258110f4d683Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-d2b94c51a4a591e3f90eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0v00-9000000000-25442110c396eb1bc0bfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05fr-0900000000-50278150b601ad9e8f07Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-35e0f674b075951ffbd3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-1900000000-e034dc2633255b5189e3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-016r-9100000000-429f5368f3041a82ca5dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-9790929fd4527de66731Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-2900000000-57504c1880586c76aa3fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9200000000-9ce799cd3421de1a0eaeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-62e0c3ca21ca97172d99Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-a680be032e1df694e8cfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9400000000-1092784dba8d3879d554Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0900000000-183681aeeabbdd961b4fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-2900000000-c87672496e2221858278Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0j4l-9000000000-444fda4e72492b61e6aaNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot 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
2464.0Log mg/kg[1400:4400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
307ChemotherapeuticsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
342Sulfonamides and trimethoprimHealthcare, pharmaceuticals & veterinary productsNot Available
496FencingBuilding & ConstructionNot Available
497FloorsBuilding & ConstructionNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
509Colour Television SystemsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
520Emergency Protective DevicesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
523Gas Filled Discharge Tubes With Solid CathodeElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
538Thin Magnetic FilmsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
541Agglomerated Sugar ProductsFood, food processing & cookwareNot Available
544Fermentation Processes For BeerFood, food processing & cookwareNot Available
545Food PreservationFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
552Processing MeatsFood, food processing & cookwareNot Available
555Bleaching AgentsHousehold cleaning & consumer productsNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot 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
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
597ChemosterilantsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
607Rodenticides(1)Agriculture & land managementNot Available
608RodenticidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
633Azo DyesTextiles, leather & furnishingsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)0.311397
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)0.389246
Click to view 3D structureDelta carbonic anhydraseQ5U9J1Conticribra weissflogiiPredicted (SEA)0.0778492
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)0.311397
Click to view 3D structureCarbonic anhydrase 4Q95323Bos taurusPredicted (SEA)0.155698
Click to view 3D structureAGAP002992-PAQ5TU56Anopheles gambiaePredicted (SEA)0.0778492
Click to view 3D structureCarbonic anhydrase 13Q9D6N1Mus musculusPredicted (SEA)0.0778492
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)0.0778492
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)0.0778492
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)0.467095
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)0.233548
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)0.155698
Click to view 3D structureCarbonate dehydrataseB2V8E3Sulfurihydrogenibium sp. (strain YO3AOP1)Predicted (SEA)0.0778492
Click to view 3D structureAstrosclerin-3A6YCJ1Astrosclera willeyanaPredicted (SEA)0.0778492
Click to view 3D structureCarbonic anhydraseO24855Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)Predicted (SEA)0.0778492
Click to view 3D structureCarbonic anhydraseQ6FTL6Candida glabrata CBS 138Predicted (SEA)0.0778492
Click to view 3D structureAlpha carbonic anhydraseB5SU02Stylophora pistillataPredicted (SEA)0.0778492
Click to view 3D structureCarbonic anhydrase, alpha familyQ31FD6Thiomicrospira crunogenaPredicted (SEA)0.0778492
Click to view 3D structureCarbonic anhydraseC0IX24Stylophora pistillataPredicted (SEA)0.0778492
Click to view 3D structureCarbonic anhydrase 15Q99N23Mus musculusPredicted (SEA)0.155698
Click to view 3D structureBeta-carbonic anhydrase 1P9WPJ7Mycobacterium tuberculosisPredicted (SEA)0.233548
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)0.155698
Click to view 3D structureCarbonic anhydrase 2P00921Bos taurusPredicted (SEA)0.0778492
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)0.233548
Click to view 3D structurePROBABLE TRANSMEMBRANE CARBONIC ANHYDRASE (CARBONATE DEHYDRATASE) (CARBONIC DEHYDRATASE)P96878Mycobacterium tuberculosisPredicted (SEA)0.233548
Concentrations
Not Available
External Links
DrugBank IDDB00259
HMDB IDHMDB0014404
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDSAN
Wikipedia LinkSulfanilamide
Chemspider ID5142
ChEBI ID45373
PubChem Compound ID5333
Kegg Compound IDC07458
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Nzila A: Inhibitors of de novo folate enzymes in Plasmodium falciparum. Drug Discov Today. 2006 Oct;11(19-20):939-44. Epub 2006 Sep 7.
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22214209
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=22342371
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=22974493
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23061287
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23065453
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23122138
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23294218
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23476893
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23561569
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=2420897
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=9639594