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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2018-05-20 20:19:54 UTC
HMDB IDHMDB0015522
Secondary Accession Numbers
  • HMDB15522
Metabolite Identification
Common NameSulfamethazine
DescriptionSulfamethazine is only found in individuals that have used or taken this drug. It is a sulfanilamide anti-infective agent. It has a spectrum of antimicrobial action similar to other sulfonamides. [PubChem]Sulfonamides inhibit the enzymatic conversion of pteridine and p-aminobenzoic acid (PABA) to dihydropteroic acid by competing with PABA for binding to dihydrofolate synthetase, an intermediate of tetrahydrofolic acid (THF) synthesis. THF is required for the synthesis of purines and dTMP and inhibition of its synthesis inhibits bacterial growth. Pyrimethamine and trimethoprim inhibit dihydrofolate reductase, another step in THF synthesis, and therefore act synergistically with the sulfonamides.
Structure
Thumb
Synonyms
ValueSource
(P-Aminobenzolsulfonyl)-2-amino-4,6-dimethylpyrimidinChEBI
2-(4-Aminobenzenesulfonamido)-4,6-dimethylpyrimidineChEBI
2-(P-Aminobenzenesulfonamido)-4,6-dimethylpyrimidineChEBI
2-Sulfanilamido-4,6-dimethylpyrimidineChEBI
4,6-Dimethyl-2-sulfanilamidopyrimidineChEBI
4-amino-N-(2,6-Dimethyl-4-pyrimidinyl)benzenesulfonamideChEBI
4-amino-N-(4,6-Dimethyl-pyrimidin-2-yl)-benzenesulfonamideChEBI
4-amino-N-(4,6-Dimethylpyrimidin-2-yl)benzenesulfonamideChEBI
6-(4'-Aminobenzol-sulfonamido)-2,4-dimethylpyrimidinChEBI
N-(4,6-Dimethyl-2-pyrimidyl)sulfanilamideChEBI
N(1)-(4,6-Dimethyl-2-pyrimidinyl)sulfanilamideChEBI
N(1)-(4,6-Dimethyl-2-pyrimidyl)sulfanilamideChEBI
SMZChEBI
SulfadimethyldiazineChEBI
SulfadimethylpyrimidineChEBI
SulfadimidinaChEBI
SulfadimidineChEBI
SulfadimidinumChEBI
SulfametazinaChEBI
SulfametazynyChEBI
SulfamethazoneChEBI
SulfamezathineChEBI
SulphadimethylpyrimidineChEBI
SulphamethazineChEBI
(P-Aminobenzolsulphonyl)-2-amino-4,6-dimethylpyrimidinGenerator
2-(4-Aminobenzenesulphonamido)-4,6-dimethylpyrimidineGenerator
2-(P-Aminobenzenesulphonamido)-4,6-dimethylpyrimidineGenerator
2-Sulphanilamido-4,6-dimethylpyrimidineGenerator
4,6-Dimethyl-2-sulphanilamidopyrimidineGenerator
4-amino-N-(2,6-Dimethyl-4-pyrimidinyl)benzenesulphonamideGenerator
4-amino-N-(4,6-Dimethyl-pyrimidin-2-yl)-benzenesulphonamideGenerator
4-amino-N-(4,6-Dimethylpyrimidin-2-yl)benzenesulphonamideGenerator
6-(4'-Aminobenzol-sulphonamido)-2,4-dimethylpyrimidinGenerator
N-(4,6-Dimethyl-2-pyrimidyl)sulphanilamideGenerator
N(1)-(4,6-Dimethyl-2-pyrimidinyl)sulphanilamideGenerator
N(1)-(4,6-Dimethyl-2-pyrimidyl)sulphanilamideGenerator
SulphadimethyldiazineGenerator
SulphadimidinaGenerator
SulphadimidineGenerator
SulphadimidinumGenerator
SulphametazinaGenerator
SulphametazynyGenerator
SulphamethazoneGenerator
SulphamezathineGenerator
SulfadimezineMeSH
Chemical FormulaC12H14N4O2S
Average Molecular Weight278.33
Monoisotopic Molecular Weight278.083746402
IUPAC Name4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzene-1-sulfonamide
Traditional Namesulfamethazine
CAS Registry Number57-68-1
SMILES
CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N1
InChI Identifier
InChI=1S/C12H14N4O2S/c1-8-7-9(2)15-12(14-8)16-19(17,18)11-5-3-10(13)4-6-11/h3-7H,13H2,1-2H3,(H,14,15,16)
InChI KeyASWVTGNCAZCNNR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Pyrimidine
  • Organosulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Heteroaromatic compound
  • Aminosulfonyl compound
  • Sulfonyl
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point198.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.23 g/LNot Available
LogP0.89BIOBYTE (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP0.43ALOGPS
logP0.65ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.99ChemAxon
pKa (Strongest Basic)2.04ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.97 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity73.38 m³·mol⁻¹ChemAxon
Polarizability28.8 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6920000000-a13c01d2bec3edc41354View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0pk9-2970000000-abb9e31dc053c1d21884View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0zi0-0590000000-2e8e1e943731aa842e16View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0kmi-0950000000-9e91e580b580594989a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0920000000-216c25f077b257c6979dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-127b8b6e862f77ce8c13View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0090000000-4841dadd912e95b736ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0910000000-fbf298bf77be3c0c7d4aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-92cfb9d3f1565228cb1bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0690000000-6900746badf188ab1500View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0abi-1910000000-5d3d9cc74470d1da9673View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0abc-3900000000-10a72542fb3fce7c8e67View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05fu-5900000000-0ad8b99c3c478536a01eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0avl-8900000000-d30171fd393f511058d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-bf48a8bbb6d06696db15View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0690000000-4789a5291d234b5d0375View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0abi-1910000000-2364d173d7cd8dae0c76View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0abc-3900000000-330131b76908d2b6ec6dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05fu-6900000000-0437ddca2816d4b382adView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0603-7900000000-71014d7adacf773403b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0190000000-00e6d87c3b30a2c4cb91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adi-1950000000-789548469cba1e744cd0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06fr-9500000000-912f06e7583c387fefbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-7c8b49420ed82f7767a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0290000000-66824a2df87f75830773View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-6900000000-4887ad72b8bb59f56122View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01582 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01582 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01582
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010660
KNApSAcK IDNot Available
Chemspider ID5136
KEGG Compound IDC19530
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfadimidine
METLIN IDNot Available
PubChem Compound5327
PDB IDNot Available
ChEBI ID102265
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available