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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 IDHMDB0015521
Secondary Accession Numbers
  • HMDB15521
Metabolite Identification
Common NameSulfamerazine
DescriptionSulfamerazine is only found in individuals that have used or taken this drug.It is a sulfanilamide that is used as an antibacterial agent. [PubChem]Sulfamerazine is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA) for binding to dihydropteroate synthetase (dihydrofolate synthetase). Sulfamerazine is bacteriostatic in nature. Inhibition of dihydrofolic acid synthesis decreases the synthesis of bacterial nucleotides and DNA.
Structure
Data?1582753306
Synonyms
ValueSource
(p-Aminobenzolsulfonyl)-2-amino-4-methylpyrimidinChEBI
2-(4-Aminobenzenesulfonamido)-4-methylpyrimidineChEBI
2-(p-Aminobenzolsulfonamido)-4-methylpyrimidineChEBI
2-(Sulfanilamido)-4-methylpyrimidineChEBI
2-Sulfa-4-methylpyrimidineChEBI
4-Amino-N-(4-methyl-2-pyrimidinyl)-benzenesulfonamideChEBI
N-(4-Methyl-2-pyrimidyl)sulfanilamideChEBI
N(1)-(4-Methyl-2-pyrimidinyl)sulfanilamideChEBI
SulfamerazinaChEBI
SulfamerazinumChEBI
SulfamethyldiazineChEBI
SulphamerazineChEBI
(p-Aminobenzolsulphonyl)-2-amino-4-methylpyrimidinGenerator
2-(4-Aminobenzenesulphonamido)-4-methylpyrimidineGenerator
2-(p-Aminobenzolsulphonamido)-4-methylpyrimidineGenerator
2-(Sulphanilamido)-4-methylpyrimidineGenerator
2-Sulpha-4-methylpyrimidineGenerator
4-Amino-N-(4-methyl-2-pyrimidinyl)-benzenesulphonamideGenerator
N-(4-Methyl-2-pyrimidyl)sulphanilamideGenerator
N(1)-(4-Methyl-2-pyrimidinyl)sulphanilamideGenerator
SulphamerazinaGenerator
SulphamerazinumGenerator
SulphamethyldiazineGenerator
Sulfamerazine veyx brandHMDB
TrimetoxHMDB
Veyx brand OF sulfamerazineHMDB
MethylsulfadiazineHMDB
MebacidHMDB
Chemical FormulaC11H12N4O2S
Average Molecular Weight264.304
Monoisotopic Molecular Weight264.068096338
IUPAC Name4-amino-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide
Traditional Namesulfamerazine
CAS Registry Number127-79-7
SMILES
CC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C1
InChI Identifier
InChI=1S/C11H12N4O2S/c1-8-6-7-13-11(14-8)15-18(16,17)10-4-2-9(12)3-5-10/h2-7H,12H2,1H3,(H,13,14,15)
InChI KeyQPPBRPIAZZHUNT-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

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point236 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.3 g/LNot Available
LogP0.14HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available156.267http://allccs.zhulab.cn/database/detail?ID=AllCCS00000816
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.3 g/LALOGPS
logP0.44ALOGPS
logP0.52ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)6.99ChemAxon
pKa (Strongest Basic)2.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.97 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.79 m³·mol⁻¹ChemAxon
Polarizability26.51 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]+161.62231661259
DarkChem[M-H]-163.22731661259
DeepCCS[M+H]+159.79630932474
DeepCCS[M-H]-157.43830932474
DeepCCS[M-2H]-190.32430932474
DeepCCS[M+Na]+165.8930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SulfamerazineCC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C14087.6Standard polar33892256
SulfamerazineCC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C12548.2Standard non polar33892256
SulfamerazineCC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C12541.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Sulfamerazine,1TMS,isomer #1CC1=CC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N12778.7Semi standard non polar33892256
Sulfamerazine,1TMS,isomer #1CC1=CC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N12462.0Standard non polar33892256
Sulfamerazine,1TMS,isomer #1CC1=CC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N13726.0Standard polar33892256
Sulfamerazine,1TMS,isomer #2CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N12543.6Semi standard non polar33892256
Sulfamerazine,1TMS,isomer #2CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N12419.7Standard non polar33892256
Sulfamerazine,1TMS,isomer #2CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N13876.8Standard polar33892256
Sulfamerazine,2TMS,isomer #1CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N12550.1Semi standard non polar33892256
Sulfamerazine,2TMS,isomer #1CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N12537.0Standard non polar33892256
Sulfamerazine,2TMS,isomer #1CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N[Si](C)(C)C)C=C2)=N13399.2Standard polar33892256
Sulfamerazine,2TMS,isomer #2CC1=CC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N12573.3Semi standard non polar33892256
Sulfamerazine,2TMS,isomer #2CC1=CC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N12552.2Standard non polar33892256
Sulfamerazine,2TMS,isomer #2CC1=CC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N13523.6Standard polar33892256
Sulfamerazine,3TMS,isomer #1CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N12437.9Semi standard non polar33892256
Sulfamerazine,3TMS,isomer #1CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N12655.3Standard non polar33892256
Sulfamerazine,3TMS,isomer #1CC1=CC=NC(N([Si](C)(C)C)S(=O)(=O)C2=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C=C2)=N13246.1Standard polar33892256
Sulfamerazine,1TBDMS,isomer #1CC1=CC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N13005.9Semi standard non polar33892256
Sulfamerazine,1TBDMS,isomer #1CC1=CC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N12684.6Standard non polar33892256
Sulfamerazine,1TBDMS,isomer #1CC1=CC=NC(NS(=O)(=O)C2=CC=C(N[Si](C)(C)C(C)(C)C)C=C2)=N13768.3Standard polar33892256
Sulfamerazine,1TBDMS,isomer #2CC1=CC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N12793.4Semi standard non polar33892256
Sulfamerazine,1TBDMS,isomer #2CC1=CC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N12638.0Standard non polar33892256
Sulfamerazine,1TBDMS,isomer #2CC1=CC=NC(N([Si](C)(C)C(C)(C)C)S(=O)(=O)C2=CC=C(N)C=C2)=N13854.4Standard polar33892256
Sulfamerazine,2TBDMS,isomer #1CC1=CC=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)=N13004.0Semi standard non polar33892256
Sulfamerazine,2TBDMS,isomer #1CC1=CC=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)=N12984.6Standard non polar33892256
Sulfamerazine,2TBDMS,isomer #1CC1=CC=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)=N13475.9Standard polar33892256
Sulfamerazine,2TBDMS,isomer #2CC1=CC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N13094.2Semi standard non polar33892256
Sulfamerazine,2TBDMS,isomer #2CC1=CC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N12980.8Standard non polar33892256
Sulfamerazine,2TBDMS,isomer #2CC1=CC=NC(NS(=O)(=O)C2=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2)=N13555.3Standard polar33892256
Sulfamerazine,3TBDMS,isomer #1CC1=CC=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)=N13149.5Semi standard non polar33892256
Sulfamerazine,3TBDMS,isomer #1CC1=CC=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)=N13338.5Standard non polar33892256
Sulfamerazine,3TBDMS,isomer #1CC1=CC=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)=N13398.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sulfamerazine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9630000000-7f08d04a103b7e16f1262017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sulfamerazine 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 - Sulfamerazine LC-ESI-qTof , Positive-QTOFsplash10-0bt9-4900000000-1429f19666bf05cae9622017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamerazine LC-ESI-QTOF , positive-QTOFsplash10-0aou-1920000000-06a82249586c8821f9d32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamerazine , positive-QTOFsplash10-0bt9-4900000000-1429f19666bf05cae9622017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Sulfamerazine -1V, Positive-QTOFsplash10-0aou-1920000000-418893a0c51582391ad42021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamerazine 10V, Positive-QTOFsplash10-014i-0190000000-74f76987a0c498d6bca12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamerazine 20V, Positive-QTOFsplash10-066r-2960000000-fe211aa71f3a8480b97c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamerazine 40V, Positive-QTOFsplash10-00mo-9100000000-7b53bc2852347d4eb65a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamerazine 10V, Negative-QTOFsplash10-03di-0090000000-c8b827438334ef9362a12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamerazine 20V, Negative-QTOFsplash10-03dj-1590000000-abc72f9a326e9106f00f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamerazine 40V, Negative-QTOFsplash10-0006-9400000000-adca0ea9c658e9952d5a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamerazine 10V, Positive-QTOFsplash10-014i-0090000000-d2eef97caf4d75ad84662021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamerazine 20V, Positive-QTOFsplash10-052f-9430000000-d161431499729de125e02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamerazine 40V, Positive-QTOFsplash10-014l-9000000000-246c8431b9069be152772021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamerazine 10V, Negative-QTOFsplash10-03di-0090000000-961f60caf9f0b5d9c6072021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamerazine 20V, Negative-QTOFsplash10-03di-1290000000-fff5d1edd43fea6c5e0b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sulfamerazine 40V, Negative-QTOFsplash10-014l-9200000000-652240a00ecd796e0b7b2021-10-11Wishart LabView 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 DB01581 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01581 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01581
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5134
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSulfamerazine
METLIN IDNot Available
PubChem Compound5325
PDB IDNot Available
ChEBI ID102130
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