Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:00 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
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
SulfadimezineMeSH, HMDB
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
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point198.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.23 g/LNot Available
LogP0.89BIOBYTE (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available161.714http://allccs.zhulab.cn/database/detail?ID=AllCCS00000817
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.07531661259
DarkChem[M-H]-166.54931661259
DeepCCS[M+H]+166.38430932474
DeepCCS[M-H]-164.02630932474
DeepCCS[M-2H]-196.91230932474
DeepCCS[M+Na]+172.47730932474
AllCCS[M+H]+164.032859911
AllCCS[M+H-H2O]+160.332859911
AllCCS[M+NH4]+167.332859911
AllCCS[M+Na]+168.332859911
AllCCS[M-H]-161.932859911
AllCCS[M+Na-2H]-161.932859911
AllCCS[M+HCOO]-162.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SulfamethazineCC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N14144.7Standard polar33892256
SulfamethazineCC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N12597.0Standard non polar33892256
SulfamethazineCC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=N12605.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sulfamethazine,1TMS,isomer #1CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N12852.2Semi standard non polar33892256
Sulfamethazine,1TMS,isomer #1CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N12551.0Standard non polar33892256
Sulfamethazine,1TMS,isomer #1CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N13838.1Standard polar33892256
Sulfamethazine,1TMS,isomer #2CC1=CC(C)=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N12596.4Semi standard non polar33892256
Sulfamethazine,1TMS,isomer #2CC1=CC(C)=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N12501.9Standard non polar33892256
Sulfamethazine,1TMS,isomer #2CC1=CC(C)=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N13979.8Standard polar33892256
Sulfamethazine,2TMS,isomer #1CC1=CC(C)=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N12614.7Semi standard non polar33892256
Sulfamethazine,2TMS,isomer #1CC1=CC(C)=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N12630.8Standard non polar33892256
Sulfamethazine,2TMS,isomer #1CC1=CC(C)=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N13475.3Standard polar33892256
Sulfamethazine,2TMS,isomer #2CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N12630.4Semi standard non polar33892256
Sulfamethazine,2TMS,isomer #2CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N12639.5Standard non polar33892256
Sulfamethazine,2TMS,isomer #2CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N13588.1Standard polar33892256
Sulfamethazine,3TMS,isomer #1CC1=CC(C)=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N12499.0Semi standard non polar33892256
Sulfamethazine,3TMS,isomer #1CC1=CC(C)=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N12759.0Standard non polar33892256
Sulfamethazine,3TMS,isomer #1CC1=CC(C)=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N13311.1Standard polar33892256
Sulfamethazine,1TBDMS,isomer #1CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N13069.8Semi standard non polar33892256
Sulfamethazine,1TBDMS,isomer #1CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N12769.9Standard non polar33892256
Sulfamethazine,1TBDMS,isomer #1CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N13849.1Standard polar33892256
Sulfamethazine,1TBDMS,isomer #2CC1=CC(C)=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N12865.0Semi standard non polar33892256
Sulfamethazine,1TBDMS,isomer #2CC1=CC(C)=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N12723.3Standard non polar33892256
Sulfamethazine,1TBDMS,isomer #2CC1=CC(C)=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N13934.3Standard polar33892256
Sulfamethazine,2TBDMS,isomer #1CC1=CC(C)=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)=N13061.7Semi standard non polar33892256
Sulfamethazine,2TBDMS,isomer #1CC1=CC(C)=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)=N13086.2Standard non polar33892256
Sulfamethazine,2TBDMS,isomer #1CC1=CC(C)=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)=N13544.1Standard polar33892256
Sulfamethazine,2TBDMS,isomer #2CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N13148.6Semi standard non polar33892256
Sulfamethazine,2TBDMS,isomer #2CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N13070.2Standard non polar33892256
Sulfamethazine,2TBDMS,isomer #2CC1=CC(C)=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N13606.7Standard polar33892256
Sulfamethazine,3TBDMS,isomer #1CC1=CC(C)=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)=N13208.3Semi standard non polar33892256
Sulfamethazine,3TBDMS,isomer #1CC1=CC(C)=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)=N13448.5Standard non polar33892256
Sulfamethazine,3TBDMS,isomer #1CC1=CC(C)=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)=N13458.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sulfamethazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-6920000000-a13c01d2bec3edc413542017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfamethazine 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 - Sulfamethazine LC-ESI-QTOF , positive-QTOFsplash10-0pk9-2970000000-abb9e31dc053c1d218842017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-QTOF , positive-QTOFsplash10-0zi0-0590000000-2e8e1e943731aa842e162017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-QTOF , positive-QTOFsplash10-0kmi-0950000000-9e91e580b580594989a02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-QTOF , positive-QTOFsplash10-00di-0920000000-216c25f077b257c6979d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-QTOF , positive-QTOFsplash10-00di-0900000000-127b8b6e862f77ce8c132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-QTOF , positive-QTOFsplash10-004i-0090000000-4841dadd912e95b736ce2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-000i-0910000000-fbf298bf77be3c0c7d4a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-004i-0090000000-92cfb9d3f1565228cb1b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-004i-0690000000-6900746badf188ab15002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-0abi-1910000000-5d3d9cc74470d1da96732017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-0abc-3900000000-10a72542fb3fce7c8e672017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-05fu-5900000000-0ad8b99c3c478536a01e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-0avl-8900000000-d30171fd393f511058d62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-004i-0090000000-bf48a8bbb6d06696db152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-004i-0690000000-4789a5291d234b5d03752017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-0abi-1910000000-2364d173d7cd8dae0c762017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-0abc-3900000000-330131b76908d2b6ec6d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-05fu-6900000000-0437ddca2816d4b382ad2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-0603-7900000000-71014d7adacf773403b42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-000i-0910000000-ddb50106bf908846aa9b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-0abc-2910000000-f56221aae64496f78e4b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-05fu-4900000000-95b487899628a8694b932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-000i-0920000000-e0e94f67285e005d0e3d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine LC-ESI-ITFT , positive-QTOFsplash10-000i-0910000000-6ba4c4c069a0eec7ba032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamethazine , positive-QTOFsplash10-004i-0590000000-97c8e7a982f4f8f5c92e2017-09-14HMDB team, MONAView Spectrum
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 IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available