Sulfamerazine (CED0007121)

Record Information
Version1.0
Creation Date2016-05-22 03:46:24 UTC
Update Date2026-08-18 09:04:21 UTC
Accession NumberCHEM016885
Identification
Common NameSulfamerazine
ClassSmall Molecule
Description
Sulfamerazine is an organic compound with the chemical formula C11H12N4O2S and an average molecular weight of 264.30 g/mol. Sulfamerazine belongs to the benzenesulfonamides, a subclass of benzene and substituted derivatives within the organic compounds. In terms of biological activity, it acts as an inhibitor of the protein target dihydropteroate synthase (folP). The compound is found in or released from 11 recorded sources across various sectors. Within healthcare, pharmaceuticals, and veterinary products, it is associated with antibiotics, chemotherapy, gynecologicals, and sulfonamides and trimethoprim. In the category of household cleaning and consumer products, it is linked to perfumes within detergents and soaps, tobacco smoke filters, and non-electric simulated smoking devices. It is also found in electrical and electronic equipment, specifically electrically stimulated smoking devices and electric switches. Additionally, it is recorded in drinking water and water supply, as well as in food preservation within the food, food processing, and cookware sector. Recorded routes of exposure for this compound include inhalation and oral administration.
Contaminant TypeNot Available
Chemical Structure
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 Mass264.304 g/mol
Monoisotopic Mass264.068 g/mol
CAS Registry Number127-79-7
IUPAC Name4-amino-N-(4-methylpyrimidin-2-yl)benzene-1-sulfonamide
Traditional Namesulfamerazine
SMILESCC1=NC(NS(=O)(=O)C2=CC=C(N)C=C2)=NC=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-9630000000-7f08d04a103b7e16f126Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bt9-4900000000-1429f19666bf05cae962Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aou-1920000000-06a82249586c8821f9d3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bt9-4900000000-1429f19666bf05cae962Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aou-1920000000-418893a0c51582391ad4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0190000000-74f76987a0c498d6bca1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-066r-2960000000-fe211aa71f3a8480b97cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00mo-9100000000-7b53bc2852347d4eb65aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-c8b827438334ef9362a1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03dj-1590000000-abc72f9a326e9106f00fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9400000000-adca0ea9c658e9952d5aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0090000000-d2eef97caf4d75ad8466Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-9430000000-d161431499729de125e0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014l-9000000000-246c8431b9069be15277Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-961f60caf9f0b5d9c607Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-1290000000-fff5d1edd43fea6c5e0bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014l-9200000000-652240a00ecd796e0b7bNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2500.0Log mg/kg[1400:4400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
307ChemotherapeuticsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
342Sulfonamides and trimethoprimHealthcare, pharmaceuticals & veterinary productsNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
631Anthraquinone DyesTextiles, leather & furnishingsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureCarbonic anhydrase 4Q95323Bos taurusPredicted (SEA)18.3724
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)54.1831
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)72.5555
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)63.6028
Click to view 3D structureAGAP002992-PAQ5TU56Anopheles gambiaePredicted (SEA)3.89246
Click to view 3D structureCarbonic anhydrase 13Q9D6N1Mus musculusPredicted (SEA)8.71911
Click to view 3D structureDelta carbonic anhydraseQ5U9J1Conticribra weissflogiiPredicted (SEA)7.86277
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)70.4535
Click to view 3D structureCarbonate dehydrataseB2V8E3Sulfurihydrogenibium sp. (strain YO3AOP1)Predicted (SEA)10.9767
Click to view 3D structureAstrosclerin-3A6YCJ1Astrosclera willeyanaPredicted (SEA)11.6774
Click to view 3D structureCarbonic anhydraseO24855Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)Predicted (SEA)12.3002
Click to view 3D structureCarbonic anhydraseQ6FTL6Candida glabrata CBS 138Predicted (SEA)16.6597
Click to view 3D structureAlpha carbonic anhydraseB5SU02Stylophora pistillataPredicted (SEA)10.2761
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)12.3002
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)25.1453
Click to view 3D structureCarbonic anhydrase, alpha familyQ31FD6Thiomicrospira crunogenaPredicted (SEA)10.9767
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)14.9471
Click to view 3D structureCarbonic anhydraseC0IX24Stylophora pistillataPredicted (SEA)10.2761
Click to view 3D structureBeta-carbonic anhydrase 1P9WPJ7Mycobacterium tuberculosisPredicted (SEA)17.5161
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)38.7689
Phosphatidylcholine transfer protein structureClick to view 3D structurePhosphatidylcholine transfer proteinQ9UKL6HumansPredicted (SEA)3.11397
Click to view 3D structureCarbonic anhydraseP53615Saccharomyces cerevisiae S288cPredicted (SEA)11.4438
Click to view 3D structureCarbonic anhydrase 2P9WPJ9Mycobacterium tuberculosisPredicted (SEA)3.58106
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)69.0523
Click to view 3D structureCarbonic anhydrase 15Q99N23Mus musculusPredicted (SEA)25.6902
Concentrations
Not Available
External Links
DrugBank IDDB01581
HMDB IDHMDB0015521
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkSulfamerazine
Chemspider ID5134
ChEBI ID102130
PubChem Compound ID5325
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11431418
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=13037579
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23627444
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2434548
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24508883
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=6864729