Sulfadoxine (CED0003027)

Record Information
Version1.0
Creation Date2016-05-22 03:46:20 UTC
Update Date2026-08-18 17:50:01 UTC
Accession NumberCHEM016883
Identification
Common NameSulfadoxine
ClassSmall Molecule
Description
Sulfadoxine is an organic compound with the chemical formula C12H14N4O4S and an average molecular weight of 310.33 g/mol. Sulfadoxine belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. The compound is associated with 12 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is found in antibiotics, antiprotozoals, and gynecologicals. It is also released from household cleaning and consumer products, including tobacco smoke filters, other smoking requisites, and non electric simulated smoking devices. Additionally, it is found in drinking water and water supply, as well as electrical and electronic equipment such as radio transmission systems, antennas, video games, auxiliary devices, and electrically stimulated smoking devices. Recorded routes of exposure include oral and inhalation. At the molecular level, sulfadoxine interacts with four recorded protein targets. It acts as a binder or inhibitor of dihydropteroate synthase and specifically targets dihydropteroate synthase (folP). Other recorded protein targets include amine oxidase [flavin-containing] B (MAOB) and bifunctional dihydrofolate reductase-thymidylate synthase.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
4-Sulfanilamido-5,6-dimethoxypyrimidineChEBI
SulfadoxinaChEBI
SulfadoxinumChEBI
SulforthomidineChEBI
SulphadoxineChEBI
SulphormethoxineChEBI
4-Sulphanilamido-5,6-dimethoxypyrimidineGenerator
SulphadoxinaGenerator
SulphadoxinumGenerator
SulphorthomidineGenerator
SulformethoxineGenerator
Sulfadoxine roche brandHMDB
Roche brand OF sulfadoxineHMDB
SulformetoxineHMDB
SulphormetoxinHMDB
FanasilHMDB
SulphorthodimethoxineHMDB
Chemical FormulaC12H14N4O4S
Average Molecular Mass310.329 g/mol
Monoisotopic Mass310.074 g/mol
CAS Registry Number2447-57-6
IUPAC Name4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide
Traditional Namesulfadoxine
SMILESCOC1=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC
InChI IdentifierInChI=1S/C12H14N4O4S/c1-19-10-11(14-7-15-12(10)20-2)16-21(17,18)9-5-3-8(13)4-6-9/h3-7H,13H2,1-2H3,(H,14,15,16)
InChI KeyPJSFRIWCGOHTNF-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
  • Alkyl aryl ether
  • Pyrimidine
  • Organosulfonic acid amide
  • Imidolactam
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Ether
  • Azacycle
  • Organic oxygen compound
  • Organic oxide
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • 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 Solubility0.3 g/LALOGPS
logP0.72ALOGPS
logP0.58ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)6.12ChemAxon
pKa (Strongest Basic)2.55ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area116.43 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity77.81 m³·mol⁻¹ChemAxon
Polarizability30.01 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 Spectrumsplash10-0pb9-4960000000-7bae9693017c80170870Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-3910000000-fbde0b31ef009afef44dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2901000000-8862dd6e93b57f07349bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-3910000000-fbde0b31ef009afef44dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2901000000-829e3509a57184006d4dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0309000000-1bd412483b026d7d74f0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0912000000-5c0e441629572b2c03c8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00mo-9410000000-b0f2c57374fa57bcb8f8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-02a2edbc525ff42bef1fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a6r-2195000000-24e8009c9a6ac8dcb544Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06dl-9850000000-961491cd3503d195810eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0009000000-ba17475c1b8cfb24cbbaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1903000000-4e317eeecd7fc60855a4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-9500000000-cfa956a4cdadb48dcd01Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0009000000-9966f01da719564fa0a5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1759000000-2dc8060f61a784f23466Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-4900000000-6f4adc5fd2e7a1ae7504Not 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
5058.0Log mg/kg[2800:9000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
385AntiprotozoalsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
620Card GamesRecreation & sports surfacesNot Available
630ToysRecreation & sports surfacesNot Available
642FootwearTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureCarbonic anhydrase 4Q95323Bos taurusPredicted (SEA)34.4094
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)145.422
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)115.373
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)127.206
Click to view 3D structureAGAP002992-PAQ5TU56Anopheles gambiaePredicted (SEA)11.366
Click to view 3D structureCarbonic anhydrase 13Q9D6N1Mus musculusPredicted (SEA)20.2408
Click to view 3D structureC-C chemokine receptor type 4Q8MJW8Canis lupus familiarisPredicted (SEA)1.32344
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)153.052
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)61.5787
Click to view 3D structureDelta carbonic anhydraseQ5U9J1Conticribra weissflogiiPredicted (SEA)22.2649
Click to view 3D structureCarbonic anhydraseO24855Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)Predicted (SEA)27.2472
Extracellular serine/threonine protein kinase FAM20C structureClick to view 3D structureExtracellular serine/threonine protein kinase FAM20CQ8IXL6HumansPredicted (SEA)8.79696
Click to view 3D structureCarbonate dehydrataseB2V8E3Sulfurihydrogenibium sp. (strain YO3AOP1)Predicted (SEA)27.4808
Click to view 3D structureAstrosclerin-3A6YCJ1Astrosclera willeyanaPredicted (SEA)29.3492
Click to view 3D structureCarbonic anhydraseQ6FTL6Candida glabrata CBS 138Predicted (SEA)43.8291
Click to view 3D structureAlpha carbonic anhydraseB5SU02Stylophora pistillataPredicted (SEA)26.9358
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)35.7328
Click to view 3D structureCarbonic anhydrase, alpha familyQ31FD6Thiomicrospira crunogenaPredicted (SEA)27.4808
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)41.6493
Click to view 3D structureCarbonic anhydraseC0IX24Stylophora pistillataPredicted (SEA)26.9358
Click to view 3D structureBeta-carbonic anhydrase 1P9WPJ7Mycobacterium tuberculosisPredicted (SEA)41.6493
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)74.7353
Click to view 3D structureEndothelin-1 receptorP26684Rattus norvegicusPredicted (SEA)40.9487
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)308.283
Click to view 3D structureCarbonic anhydraseP53615Saccharomyces cerevisiae S288cPredicted (SEA)28.8821
Concentrations
Not Available
External Links
DrugBank IDDB01299
HMDB IDHMDB0015413
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSulfadoxine
Chemspider ID16218
ChEBI ID9329
PubChem Compound ID17134
Kegg Compound IDC07630
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=14711594
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23183348