Sulfamonomethoxine

Basic Info

Common NameSulfamonomethoxine(F05679)
2D Structure
FRCD IDF05679
CAS Number1220-83-3
PubChem CID5332
FormulaC11H12N4O3S
IUPAC Name

4-amino-N-(6-methoxypyrimidin-4-yl)benzenesulfonamide

InChI Key

WMPXPUYPYQKQCX-UHFFFAOYSA-N

InChI

InChI=1S/C11H12N4O3S/c1-18-11-6-10(13-7-14-11)15-19(16,17)9-4-2-8(12)3-5-9/h2-7H,12H2,1H3,(H,13,14,15)

Canonical SMILES

COC1=NC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N

Isomeric SMILES

COC1=NC=NC(=C1)NS(=O)(=O)C2=CC=C(C=C2)N

Synonyms
        
            sulfamonomethoxine
        
            1220-83-3
        
            Sulfamonomethoxin
        
            Daimeton
        
            Sulfamonometoxina
        
            Sulfamonomethoxinum
        
            4-amino-N-(6-methoxypyrimidin-4-yl)benzenesulfonamide
        
            DS-36
        
            4-Amino-N-(6-methoxy-4-pyrimidinyl)benzenesulfonamide
        
            DJ-1550
Classifies
                

                  
                    Predicted: Pesticide
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 - Alkyl aryl ether - Pyrimidine - Organosulfonic acid amide - Imidolactam - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Aminosulfonyl compound - Heteroaromatic compound - Organoheterocyclic compound - Ether - Azacycle - Organic oxygen compound - Organic oxide - Amine - Organic nitrogen compound - Organopnictogen compound - Primary amine - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - 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 Weight280.302
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Complexity376
Monoisotopic Mass280.063
Exact Mass280.063
XLogP0.8
Formal Charge0
Heavy Atom Count19
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+0.9027
Human Intestinal AbsorptionHIA+0.9866
Caco-2 PermeabilityCaco2+0.5465
P-glycoprotein SubstrateNon-substrate0.8436
P-glycoprotein InhibitorNon-inhibitor0.8865
Non-inhibitor0.9646
Renal Organic Cation TransporterNon-inhibitor0.8883
Distribution
Subcellular localizationMitochondria0.5512
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6512
CYP450 2D6 SubstrateNon-substrate0.8995
CYP450 3A4 SubstrateNon-substrate0.7052
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorNon-inhibitor0.9231
CYP450 2C19 InhibitorNon-inhibitor0.9025
CYP450 3A4 InhibitorNon-inhibitor0.8309
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.6289
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9812
Non-inhibitor0.8329
AMES ToxicityNon AMES toxic0.7762
CarcinogensNon-carcinogens0.8819
Fish ToxicityLow FHMT0.7212
Tetrahymena Pyriformis ToxicityLow TPT0.5564
Honey Bee ToxicityLow HBT0.7890
BiodegradationNot ready biodegradable0.9947
Acute Oral ToxicityIV0.6259
Carcinogenicity (Three-class)Non-required0.5231
Model Value Unit
Absorption
Aqueous solubility-2.7165LogS
Caco-2 Permeability0.9850LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.4789LD50, mol/kg
Fish Toxicity2.0355pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.2599pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
Other FishJapan0.1ppm
PerciformesJapan0.1ppm
AnguilliformesJapan0.1ppm
SalmoniformesJapan0.1ppm
Chicken,Edible OffalJapan0.1ppm
Chicken,KidneyJapan0.1ppm
Chicken,LiverJapan0.1ppm
Chicken,FatJapan0.1ppm
Chicken,MuscleJapan0.1ppm
Cattle,MuscleJapan0.01ppm
Pig,Edible OffalJapan0.1ppm
Cattle,Edible OffalJapan0.05ppm
Other Terrestrial Mammals,KidneyJapan0.1ppm
Pig,KidneyJapan0.05ppm
Cattle,KidneyJapan0.05ppm
Other Terrestrial Mammals,LiverJapan0.1ppm
Pig,LiverJapan0.05ppm
Cattle,LiverJapan0.05ppm
Other Terrestrial Mammals,FatJapan0.1ppm
Pig,FatJapan0.05ppm

References

TitleJournalDatePubmed ID
Source estimation of pharmaceuticals based on catchment population and in-stream attenuation in Yodo River watershed, Japan.Sci Total Environ2018 Feb 1529751447
Detection of antibiotics in chicken eggs obtained from supermarkets in Ho ChiMinh City, Vietnam.J Environ Sci Health B2017 Jun 328281880
Distribution of sulfamonomethoxine and trimethoprim in egg yolk and white.Food Chem2015 Jul 125704680
Development and validation of an HPLC method for the determination of tensulfonamide residues in milk according to 2002/657/EC.J Sep Sci2011 Jul21644254
Analyses of sulfonamide antibiotics by a successive anion- and cation-selectiveinjection coupled to microemulsion electrokinetic chromatography.Electrophoresis2010 Jul20593402
Eco-toxic effects of sulfadiazine sodium, sulfamonomethoxine sodium and enrofloxacin on wheat, Chinese cabbage and tomato.Ecotoxicology2009 Oct19554446
A confirmatory method for the simultaneous extraction, separation, identificationand quantification of Tetracycline, Sulphonamide, Trimethoprim and Dapsoneresidues in muscle by ultra-high-performance liquid chromatography-tandem massspectrometry according to Commission Decision 2002/657/EC.J Chromatogr A2009 Nov 1319586630
Development and validation of a confirmatory method for the determination ofsulphonamides in milk by liquid chromatography with diode array detection.Anal Chim Acta2009 Apr 119286007
Development of an immunochromatographic lateral-flow test strip for rapiddetection of sulfonamides in eggs and chicken muscles.J Agric Food Chem2007 Mar 2117316015
Determining sulfamonomethoxine and its acetyl/hydroxyl metabolites in chicken plasma under organic solvent-free conditions.Anal Bioanal Chem2006 Aug16838157
[Qualification and quantification of 10 sulfonamides in animal feedstuff by high performance liquid chromatography-electrospray tandem mass spectrometry].Se Pu2005 Jul16250451
Stability of sulfonamides, nitrofurans, and chloramphenicol residues in preservedraw milk samples measured by liquid chromatography.J AOAC Int2002 Nov-Dec12477207
Liquid chromatographic determination of multiple sulfonamides, nitrofurans, andchloramphenicol residues in pasteurized milk.J AOAC Int2002 Jan-Feb11878601
High-performance liquid chromatographic procedure for routine residue monitoring of seven sulfonamides in milk.Fresenius J Anal Chem2001 Dec11769794
Transference of dietary veterinary drugs into eggs.Vet Res Commun2001 Dec11767011
Determination of sulfonamides in swine meat by immunoaffinity chromatography.J AOAC Int2000 Jul-Aug10995109
High-performance liquid chromatographic method for the rapid and simultaneousdetermination of sulfamonomethoxine, miloxacin and oxolinic acid in serum andmuscle of cultured fish.J Chromatogr B Biomed Appl1996 Jun 288832440