Sulfathiazole

Basic Info

Common NameSulfathiazole(F05677)
2D Structure
FRCD IDF05677
CAS Number72-14-0
PubChem CID5340
FormulaC9H9N3O2S2
IUPAC Name

4-amino-N-(1,3-thiazol-2-yl)benzenesulfonamide

InChI Key

JNMRHUJNCSQMMB-UHFFFAOYSA-N

InChI

InChI=1S/C9H9N3O2S2/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9/h1-6H,10H2,(H,11,12)

Canonical SMILES

C1=CC(=CC=C1N)S(=O)(=O)NC2=NC=CS2

Isomeric SMILES

C1=CC(=CC=C1N)S(=O)(=O)NC2=NC=CS2

Synonyms
        
            sulfathiazole
        
            72-14-0
        
            Sulphathiazole
        
            Sulfathiazol
        
            Sulfanilamidothiazole
        
            2-Sulfanilamidothiazole
        
            Norsulfazole
        
            2-Sulfonamidothiazole
        
            Norsulfasol
        
            Thiazamide
Classifies
                

                  
                    Veterinary Drug
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzenesulfonamides
Intermediate Tree NodesNot available
Direct ParentAminobenzenesulfonamides
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsAminobenzenesulfonamide - Benzenesulfonyl group - Aniline or substituted anilines - Organosulfonic acid amide - Azole - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Thiazole - Aminosulfonyl compound - Heteroaromatic compound - Organoheterocyclic compound - Azacycle - Organonitrogen compound - Amine - Organic oxygen compound - Organic nitrogen compound - Organosulfur compound - Organopnictogen compound - Primary amine - Hydrocarbon derivative - Organic oxide - Aromatic heteromonocyclic compound
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.

Properties

Property NameProperty Value
Molecular Weight255.31
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count3
Complexity320
Monoisotopic Mass255.014
Exact Mass255.014
XLogP0.1
Formal Charge0
Heavy Atom Count16
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9460
Human Intestinal AbsorptionHIA+0.9087
Caco-2 PermeabilityCaco2-0.6975
P-glycoprotein SubstrateNon-substrate0.9186
P-glycoprotein InhibitorNon-inhibitor0.9445
Non-inhibitor0.8896
Renal Organic Cation TransporterNon-inhibitor0.8926
Distribution
Subcellular localizationMitochondria0.4574
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8236
CYP450 2D6 SubstrateNon-substrate0.9083
CYP450 3A4 SubstrateNon-substrate0.7952
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9070
CYP450 2D6 InhibitorNon-inhibitor0.9338
CYP450 2C19 InhibitorNon-inhibitor0.9026
CYP450 3A4 InhibitorNon-inhibitor0.8309
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.7817
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9396
Non-inhibitor0.9101
AMES ToxicityNon AMES toxic0.9151
CarcinogensNon-carcinogens0.9034
Fish ToxicityLow FHMT0.6670
Tetrahymena Pyriformis ToxicityHigh TPT0.5448
Honey Bee ToxicityLow HBT0.7906
BiodegradationNot ready biodegradable0.9776
Acute Oral ToxicityIII0.6733
Carcinogenicity (Three-class)Non-required0.5316
Model Value Unit
Absorption
Aqueous solubility-2.4428LogS
Caco-2 Permeability0.5138LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.7929LD50, mol/kg
Fish Toxicity2.1796pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2297pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Edible Tissues Of SwineUnited States0.1ppm
Other Poultry Animals,Edible OffalJapan0.1ppm
Chicken,Edible OffalJapan0.1ppm
Other Poultry Animals,KidneyJapan0.1ppm
Chicken,KidneyJapan0.1ppm
Other Poultry Animals,LiverJapan0.1ppm
Chicken,LiverJapan0.1ppm
Other Poultry Animals,FatJapan0.1ppm
Chicken,FatJapan0.1ppm
Other Poultry Animals,MuscleJapan0.1ppm
Chicken,MuscleJapan0.1ppm
MilkJapan0.09ppm
Other Terrestrial Mammals,Edible OffalJapan0.1ppm
Pig,Edible OffalJapan0.1ppm
Cattle,Edible OffalJapan0.1ppm
Other Terrestrial Mammals,KidneyJapan0.1ppm
Pig,KidneyJapan0.1ppm
Cattle,KidneyJapan0.1ppm
Other Terrestrial Mammals,LiverJapan0.1ppm
Pig,LiverJapan0.1ppm

References

TitleJournalDatePubmed ID
Quantitative analysis of veterinary drugs in bovine muscle and milk by liquidchromatography quadrupole time-of-flight mass spectrometry.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2017Jul28524783
Towards the determination of sulfonamides in meat samples: A magnetic andmesoporous metal-organic framework as an efficient sorbent for magnetic solidphase extraction combined with high-performance liquid chromatography.J Chromatogr A2017 Jun 228408042
Determination of Sulfonamide Residues in Food by Capillary Zone Electrophoresiswith On-Line Chemiluminescence Detection Based on an Ag(III) Complex.Int J Mol Sci2017 Jun 1628621728
Development of a single-run analytical method for the detection of ten multiclassemerging contaminants in agricultural soil using an acetate-buffered QuEChERSmethod coupled with LC-MS/MS.J Sep Sci2017 Jan27863002
Uptake of the veterinary antibiotics chlortetracycline, enrofloxacin, andsulphathiazole from soil by radish.Sci Total Environ2017 Dec 1528668743
Short communication: Drug residues in goat milk after prophylactic use ofantibiotics in intravaginal sponges for estrus synchronization.J Dairy Sci2016 Jan26585470
Degradation of Oxytetracycline, Streptomycin, Sulphathiazole and Chloramphenicol Residues in Different Types of Honey.Food Technol Biotechnol2015 Jun27904344
Effects of antibiotic growth promoter and characterization of ecologicalsuccession in Swine gut microbiota.J Microbiol Biotechnol2015 Apr25370726
Simultaneous determination of 14 sulfonamides and tetracyclines in biogas plants by liquid-liquid-extraction and liquid chromatography tandem mass spectrometry.Anal Bioanal Chem2014 Apr24535685
Biocompatibility and antibacterial activity of photolytic products ofsulfonamides.Chemosphere2014 Apr24321335
An inter-laboratory validation of a multiplex dipstick assay for four classes of antibiotics in honey.Anal Bioanal Chem2013 Sep23820949
Detection of harmful residues in honey using terahertz time-domain spectroscopy.Appl Spectrosc2013 Nov24160877
Development and validation of a procedure for determination of sulfonamideresidues in pasteurized milk using modified QuEChERS method and liquidchromatography/tandem mass spectrometry.J AOAC Int2012 Sep-Oct23175989
Nano-liquid chromatography coupled with mass spectrometry: separation ofsulfonamides employing non-porous core-shell particles.J Chromatogr A2012 Sep 1422481108
Reduction of antibiotics using microorganisms containing glutathioneS-transferases under immobilized conditions.Environ Toxicol Pharmacol2012 Sep22706454
Determination of sulphonamide residues in cattle meats by the Charm-II system andvalidation with high performance liquid chromatography with fluorescencedetection.Food Chem2012 Oct 125005994
Validation of a commercial receptor kit Sulfasensor Honey for the screening ofsulfonamides in honey according to Commission Decision 2002/657/EC.Food Addit Contam Part A Chem Anal Control Expo Risk Assess201222455559
Influence of water and food consumption on inadvertent antibiotics intake amonggeneral population.Environ Res2010 Oct20624619
A multivariate multianalyte screening method for sulfonamides in milk based onfront-face fluorescence spectroscopy.Anal Chim Acta2010 Jan 1120005325
Determination of ten sulphonamides in egg by liquid chromatography-tandem massspectrometry.Anal Chim Acta2009 Apr 119286032