Sulfacetamide

Basic Info

Common NameSulfacetamide(F05886)
2D Structure
FRCD IDF05886
CAS Number144-80-9
PubChem CID5320
FormulaC8H10N2O3S
IUPAC Name

N-(4-aminophenyl)sulfonylacetamide

InChI Key

SKIVFJLNDNKQPD-UHFFFAOYSA-N

InChI

InChI=1S/C8H10N2O3S/c1-6(11)10-14(12,13)8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11)

Canonical SMILES

CC(=O)NS(=O)(=O)C1=CC=C(C=C1)N

Isomeric SMILES

CC(=O)NS(=O)(=O)C1=CC=C(C=C1)N

Synonyms
        
            N-((4-Aminophenyl)sulfonyl)acetamide
        
            sulfacetamide
        
            144-80-9
        
            Sulphacetamide
        
            Acetosulfamine
        
            N-Acetylsulfanilamide
        
            Acetosulfamin
        
            Albucid
        
            N-Sulfanilylacetamide
        
            Sulfacetimide
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 homomonocyclic compounds
SubstituentsAminobenzenesulfonamide - Benzenesulfonyl group - Aniline or substituted anilines - Organic sulfonic acid or derivatives - Organosulfonic acid or derivatives - Sulfonyl - Acetamide - Aminosulfonyl compound - Amino acid or derivatives - Carboxylic acid derivative - Organic oxide - Organopnictogen compound - Primary amine - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Amine - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Aromatic homomonocyclic 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 Weight214.239
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Complexity299
Monoisotopic Mass214.041
Exact Mass214.041
XLogP-1
Formal Charge0
Heavy Atom Count14
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+0.9881
Human Intestinal AbsorptionHIA+0.9912
Caco-2 PermeabilityCaco2-0.5396
P-glycoprotein SubstrateNon-substrate0.8806
P-glycoprotein InhibitorNon-inhibitor0.9743
Non-inhibitor0.9449
Renal Organic Cation TransporterNon-inhibitor0.9484
Distribution
Subcellular localizationMitochondria0.6595
Metabolism
CYP450 2C9 SubstrateNon-substrate0.6975
CYP450 2D6 SubstrateNon-substrate0.9058
CYP450 3A4 SubstrateNon-substrate0.7775
CYP450 1A2 InhibitorNon-inhibitor0.9609
CYP450 2C9 InhibitorNon-inhibitor0.9595
CYP450 2D6 InhibitorNon-inhibitor0.9312
CYP450 2C19 InhibitorNon-inhibitor0.9546
CYP450 3A4 InhibitorNon-inhibitor0.9552
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.8371
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9919
Non-inhibitor0.9775
AMES ToxicityNon AMES toxic0.9279
CarcinogensNon-carcinogens0.8623
Fish ToxicityHigh FHMT0.5295
Tetrahymena Pyriformis ToxicityHigh TPT0.5441
Honey Bee ToxicityLow HBT0.7759
BiodegradationNot ready biodegradable0.9686
Acute Oral ToxicityIII0.8236
Carcinogenicity (Three-class)Non-required0.5176
Model Value Unit
Absorption
Aqueous solubility-1.2924LogS
Caco-2 Permeability0.9982LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.7849LD50, mol/kg
Fish Toxicity2.4207pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.1173pIGC50, ug/L

MRLs

FoodProduct CodeCountryMRLsApplication DateNotes
MilkJapan0.01ppm
Other Terrestrial Mammals,Edible OffalJapan0.1ppm
Cattle,Edible OffalJapan0.1ppm
Other Terrestrial Mammals,KidneyJapan0.1ppm
Cattle,KidneyJapan0.1ppm
Other Terrestrial Mammals,LiverJapan0.1ppm
Cattle,LiverJapan0.1ppm
Other Terrestrial Mammals,FatJapan0.1ppm
Cattle,FatJapan0.1ppm
Other Terrestrial Mammals,MuscleJapan0.1ppm
Cattle,MuscleJapan0.1ppm

References

TitleJournalDatePubmed ID
Survey of Veterinary Drug Residues in Raw Milk in Hebei Province, China.J Food Prot2017 Oct 17:1890-189629039709
A Drug Combination Screen Identifies Drugs Active against Amoxicillin-InducedRound Bodies of In Vitro Borrelia burgdorferi Persisters from an FDA DrugLibrary.Front Microbiol2016 May 2327242757
Rapid determination of sulfonamide residues in pork by surface-modifiedhydrophilic electrospun nanofibrous membrane solid-phase extraction combined withultra-performance liquid chromatography.Anal Bioanal Chem2016 Aug27235160
Optimal conditions for determination of zinc bacitracin, polymyxin B,oxytetracycline and sulfacetamide in animal feed by micellar electrokineticcapillary chromatography.Food Addit Contam Part A Chem Anal Control Expo Risk Assess2008Apr18348041
Broad-specificity immunoassays for sulfonamide detection: immunochemical strategyfor generic antibodies and competitors.Anal Chem2006 Mar 116503608
Topical metronidazole combination therapy in the clinical management of rosacea.J Drugs Dermatol2005 Jul-Aug16004021
Molecular modeling of hapten structure and relevance to broad specificityimmunoassay of sulfonamide antibiotics.Bioconjug Chem1999 Jul-Aug10411455
Confirmatory method for sulfonamide residues in animal tissues by gaschromatography and pulsed positive ion-negative ion-chemical ionization massspectrometry.J AOAC Int1993 Sep-Oct8241826