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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:34 UTC
HMDB IDHMDB0015413
Secondary Accession Numbers
  • HMDB15413
Metabolite Identification
Common NameSulfadoxine
DescriptionSulfadoxine is only found in individuals that have used or taken this drug. It is a long acting sulfonamide that is used, usually in combination with other drugs, for respiratory, urinary tract, and malarial infections. [PubChem]Sulfadoxine is a sulfa drug, often used in combination with pyrimethamine to treat malaria. This medicine may also be used to prevent malaria in people who are living in, or will be traveling to, an area where there is a chance of getting malaria. Sulfadoxine targets Plasmodium dihydropteroate synthase and dihydrofolate reductase. Sulfa drugs or Sulfonamides are antimetabolites. They compete with para-aminobenzoic acid (PABA) for incorporation into folic acid. The action of sulfonamides exploits the difference between mammal cells and other kinds of cells in their folic acid metabolism. All cells require folic acid for growth. Folic acid (as a vitamin) diffuses or is transported into human cells. However, folic acid cannot cross bacterial (and certain protozoan) cell walls by diffusion or active transport. For this reason bacteria must synthesize folic acid from p-aminobenzoic acid.
Structure
Data?1582753294
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 Weight310.329
Monoisotopic Molecular Weight310.073575646
IUPAC Name4-amino-N-(5,6-dimethoxypyrimidin-4-yl)benzene-1-sulfonamide
Traditional Namesulfadoxine
CAS Registry Number2447-57-6
SMILES
COC1=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point190 - 194 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.3 g/LNot Available
LogP0.70SANGSTER (1994)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM165.330932474
[M+H]+Not Available166.243http://allccs.zhulab.cn/database/detail?ID=AllCCS00000774
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP10(0.72) g/LALOGPS
logP10(0.58) g/LChemAxon
logS10(-3) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+170.84331661259
DarkChem[M-H]-170.92631661259
DeepCCS[M+H]+167.26430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SulfadoxineCOC1=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC4362.2Standard polar33892256
SulfadoxineCOC1=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC2842.9Standard non polar33892256
SulfadoxineCOC1=NC=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1OC2766.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sulfadoxine,1TMS,isomer #1COC1=NC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=C1OC3006.8Semi standard non polar33892256
Sulfadoxine,1TMS,isomer #1COC1=NC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=C1OC2754.2Standard non polar33892256
Sulfadoxine,1TMS,isomer #1COC1=NC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=C1OC4375.8Standard polar33892256
Sulfadoxine,1TMS,isomer #2COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=C1OC2735.6Semi standard non polar33892256
Sulfadoxine,1TMS,isomer #2COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=C1OC2685.9Standard non polar33892256
Sulfadoxine,1TMS,isomer #2COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=C1OC4480.9Standard polar33892256
Sulfadoxine,2TMS,isomer #1COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=C1OC2800.6Semi standard non polar33892256
Sulfadoxine,2TMS,isomer #1COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=C1OC2808.8Standard non polar33892256
Sulfadoxine,2TMS,isomer #1COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=C1OC3887.0Standard polar33892256
Sulfadoxine,2TMS,isomer #2COC1=NC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=C1OC2827.2Semi standard non polar33892256
Sulfadoxine,2TMS,isomer #2COC1=NC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=C1OC2842.7Standard non polar33892256
Sulfadoxine,2TMS,isomer #2COC1=NC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=C1OC4054.7Standard polar33892256
Sulfadoxine,3TMS,isomer #1COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=C1OC2726.4Semi standard non polar33892256
Sulfadoxine,3TMS,isomer #1COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=C1OC2936.2Standard non polar33892256
Sulfadoxine,3TMS,isomer #1COC1=NC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=C1OC3639.3Standard polar33892256
Sulfadoxine,1TBDMS,isomer #1COC1=NC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=C1OC3246.6Semi standard non polar33892256
Sulfadoxine,1TBDMS,isomer #1COC1=NC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=C1OC2978.7Standard non polar33892256
Sulfadoxine,1TBDMS,isomer #1COC1=NC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=C1OC4334.8Standard polar33892256
Sulfadoxine,1TBDMS,isomer #2COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=C1OC3000.4Semi standard non polar33892256
Sulfadoxine,1TBDMS,isomer #2COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=C1OC2905.1Standard non polar33892256
Sulfadoxine,1TBDMS,isomer #2COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=C1OC4413.8Standard polar33892256
Sulfadoxine,2TBDMS,isomer #1COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=C1OC3258.0Semi standard non polar33892256
Sulfadoxine,2TBDMS,isomer #1COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=C1OC3276.6Standard non polar33892256
Sulfadoxine,2TBDMS,isomer #1COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=C1OC3883.6Standard polar33892256
Sulfadoxine,2TBDMS,isomer #2COC1=NC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=C1OC3297.7Semi standard non polar33892256
Sulfadoxine,2TBDMS,isomer #2COC1=NC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=C1OC3259.5Standard non polar33892256
Sulfadoxine,2TBDMS,isomer #2COC1=NC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=C1OC3992.2Standard polar33892256
Sulfadoxine,3TBDMS,isomer #1COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=C1OC3374.9Semi standard non polar33892256
Sulfadoxine,3TBDMS,isomer #1COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=C1OC3633.1Standard non polar33892256
Sulfadoxine,3TBDMS,isomer #1COC1=NC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=C1OC3724.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sulfadoxine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-4960000000-7bae9693017c801708702017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfadoxine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadoxine LC-ESI-qTof , Positive-QTOFsplash10-0a4i-3910000000-fbde0b31ef009afef44d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadoxine LC-ESI-QTOF , positive-QTOFsplash10-0a4i-2901000000-8862dd6e93b57f07349b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadoxine , positive-QTOFsplash10-0a4i-3910000000-fbde0b31ef009afef44d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfadoxine -1V, Positive-QTOFsplash10-0a4i-2901000000-829e3509a57184006d4d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadoxine 10V, Positive-QTOFsplash10-03di-0309000000-1bd412483b026d7d74f02016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadoxine 20V, Positive-QTOFsplash10-0a4i-0912000000-5c0e441629572b2c03c82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadoxine 40V, Positive-QTOFsplash10-00mo-9410000000-b0f2c57374fa57bcb8f82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadoxine 10V, Negative-QTOFsplash10-0a4i-0009000000-02a2edbc525ff42bef1f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadoxine 20V, Negative-QTOFsplash10-0a6r-2195000000-24e8009c9a6ac8dcb5442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadoxine 40V, Negative-QTOFsplash10-06dl-9850000000-961491cd3503d195810e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadoxine 10V, Positive-QTOFsplash10-03di-0009000000-ba17475c1b8cfb24cbba2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadoxine 20V, Positive-QTOFsplash10-0a4i-1903000000-4e317eeecd7fc60855a42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadoxine 40V, Positive-QTOFsplash10-00kf-9500000000-cfa956a4cdadb48dcd012021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadoxine 10V, Negative-QTOFsplash10-0a4i-0009000000-9966f01da719564fa0a52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadoxine 20V, Negative-QTOFsplash10-0a4i-1759000000-2dc8060f61a784f234662021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfadoxine 40V, Negative-QTOFsplash10-0a4i-4900000000-6f4adc5fd2e7a1ae75042021-10-11Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01299 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01299 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01299
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID16218
KEGG Compound IDC07630
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfadoxine
METLIN IDNot Available
PubChem Compound17134
PDB IDNot Available
ChEBI ID9329
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available