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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:46 UTC
HMDB IDHMDB0015522
Secondary Accession Numbers
  • HMDB15522
Metabolite Identification
Common NameSulfamethazine
DescriptionSulfamethazine, also known as sulfadimidine or sulphamezathine, 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. Sulfamethazine is a drug. Sulfamethazine is a moderately basic compound (based on its pKa). Sulfadimidine or sulfamethazine is a sulfonamide antibacterial. In Pakistan, it is available with the brand name of "Sanadine-33.3 %" as potential treatment of E-coli enteritis in veterinary medicine. ^c "SMZ" is not found in databases, but often seen in the published literature; it could however be confused with sulfamethoxazole, also seen abbreviated SMZ. [9]^a Abbreviations are not found in the databases (such as ChemDB, ChemIDplus, PubChem), but often seen in the published literature. There are non-standardizeda abbreviations for it as "sulfadimidine" (abbreviated SDI and more commonly but less reliablyb SDD) and as "sulfamethazine" (abbreviated SMT and more commonly but less reliablyc SMZ). ^b "SDD" is not found in databases, but often seen in the published literature; it could however be confused with Tiferron/Sodium catechol sulfate (1,2-Dihydroxybenzene-3,5-disulfonic acid disodium Salt), uncommon but found officially abbreviated SDD in the ChemIDplus database. Other names include sulfadimerazine, sulfadimezine, and sulphadimethylpyrimidine.
Structure
Data?1582753306
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
SulfadimezineHMDB
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
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
  • 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6920000000-a13c01d2bec3edc41354Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0pk9-2970000000-abb9e31dc053c1d21884Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0zi0-0590000000-2e8e1e943731aa842e16Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0kmi-0950000000-9e91e580b580594989a0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0920000000-216c25f077b257c6979dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0900000000-127b8b6e862f77ce8c13Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-0090000000-4841dadd912e95b736ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0910000000-fbf298bf77be3c0c7d4aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-92cfb9d3f1565228cb1bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0690000000-6900746badf188ab1500Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0abi-1910000000-5d3d9cc74470d1da9673Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0abc-3900000000-10a72542fb3fce7c8e67Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05fu-5900000000-0ad8b99c3c478536a01eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0avl-8900000000-d30171fd393f511058d6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0090000000-bf48a8bbb6d06696db15Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0690000000-4789a5291d234b5d0375Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0abi-1910000000-2364d173d7cd8dae0c76Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0abc-3900000000-330131b76908d2b6ec6dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-05fu-6900000000-0437ddca2816d4b382adSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0603-7900000000-71014d7adacf773403b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0190000000-00e6d87c3b30a2c4cb91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adi-1950000000-789548469cba1e744cd0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06fr-9500000000-912f06e7583c387fefbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-7c8b49420ed82f7767a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0290000000-66824a2df87f75830773Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-6900000000-4887ad72b8bb59f56122Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01582 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available