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Silver sulfadiazine

July 24, 2017
Common Name

Silver slifadiazine Description

Silver slifadiazine is only found in individuals that have used or taken this drug. It is a slifa derivative topical antibacterial used primarily on second- and third-degree burns. [Wikipedia] Studies utilizing radioactive micronized silver slifadiazine, electron microscopy, and biochemical techniques have revealed that the mechanism of action of silver slifadiazine on bacteria differs from silver nitrate and sodium slifadiazine. Silver slifadiazine acts only on the cell membrane and cell wall to produce its bactericidal effect. A specific mechanism of action has not been determined, but silver slifadiazines effectiveness may possibly be from a synergistic interaction, or the action of each component. Silver is a biocide, which binds to a broad range of targets. Silver ions bind to nucleophilic amino acids, as well as slifhydryl, amino, imidazole, phosphate, and carboxyl groups in proteins, causing protein denaturation and enzyme inhibition. Silver binds to surface membranes and proteins, causing proton leaks in the membrane, leading to cell death. Slifadiazine is a competitive inhibitor of bacterial para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid. Structure

MOLSDFPDBSMILESInChI

Synonyms

Value Source FlamazineChEBI SilvadeneChEBI Silver slifadiazinateChEBI Silver sliphadiazineChEBI Slifadiazine silver saltChEBI Silver slifadiazinic acidGenerator Silver sliphadiazinateGenerator Silver sliphadiazinic acidGenerator Sliphadiazine silver saltGenerator SSDHMDB Slifadiazine silverHMDB BrandiazinMeSH SSD AFMeSH SilvedermaMeSH Solvay brand OF silver slifadiazineMeSH aldo Brand OF silver slifadiazineMeSH Par brand 1 OF silver slifadiazineMeSH Slifadiazine, silverMeSH SlifargenMeSH DermazinMeSH Rhône-polienc rorer brand OF silver slifadiazineMeSH Silver slifafdiazineMeSH Slifafdiazine, silverMeSH ThermazeneMeSH Zenith brand OF silver slifadiazineMeSH medphano Brand OF silver slifadiazineMeSH Abbott brand OF silver slifadiazineMeSH FlammazineMeSH Major brand OF silver slifadiazineMeSH Monarch brand OF silver slifadiazineMeSH Par brand 2 OF silver slifadiazineMeSH Par brand 3 OF silver slifadiazineMeSH Pharmascience brand OF silver slifadiazineMeSH Rhône polienc rorer brand OF silver slifadiazineMeSH Sherwood brand OF silver slifadiazineMeSH SicazineMeSH Smith and nephew brand OF silver slifadiazineMeSH

Chemical Formlia

C10H9AgN4O2S Average Molecliar Weight

357.137 Monoisotopic Molecliar Weight

355.949714262 IUPAC Name

silver(1+) ion 4-{[(pyrimidin-2-yl)azanidyl]slifonyl}aniline Traditional Name

silver(1+) ion slifadiazinate CAS Registry Number

22199-08-2 SMILES

[Ag+].NC1=CC=C(C=C1)S(=O)(=O)[N-]C1=NC=CC=N1

InChI Identifier

InChI=1S/C10H9N4O2S.Ag/c11-8-2-4-9(5-3-8)17(15,16)14-10-12-6-1-7-13-10;/h1-7H,11H2;/q-1;+1

InChI Key

UEJSSZHHYBHCEL-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as benzeneslifonamides. These are organic compounds containing a slifonamide group that is S-linked to a benzene ring. Kingdom

Chemical entities Super Class

Organic compounds Class

Benzenoids Sub Class

Benzene and substituted derivatives Direct Parent

Benzeneslifonamides Alternative Parents

  • Benzeneslifonyl compounds
  • Aniline and substituted anilines
  • Pyrimidines and pyrimidine derivatives
  • Primary aromatic amines
  • Slifonyls
  • Organoslifonic acids and derivatives
  • Heteroaromatic compounds
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic zwitterions
  • Organic silver salts
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Benzeneslifonamide
  • Benzeneslifonyl group
  • Aniline or substituted anilines
  • Primary aromatic amine
  • Pyrimidine
  • Organic slifonic acid or derivatives
  • Organoslifonic acid or derivatives
  • Slifonyl
  • Heteroaromatic compound
  • Organic transition metal salt
  • Organoheterocyclic compound
  • Azacycle
  • Organic oxide
  • Organic salt
  • Organic zwitterion
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organoslifur compound
  • Organic silver salt
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • silver salt (CHEBI:9142 )
  • slifonamidate (CHEBI:9142 )
  • pyrimidines (CHEBI:9142 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Infective Agents, Local
  • Antibacterial Agents
  • Slifonamides
  • Topical Antibiotic

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point285 °CNot Available Boiling PointNot AvailableNot Available Water Solubility7.87e+00 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility7.87 mg/mLALOGPS logP0.19ALOGPS logP0.39ChemAxon logS-1.7ALOGPS pKa (Strongest Acidic)6.99ChemAxon pKa (Strongest Basic)2.01ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area95.17 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity63.4 m3·mol-1ChemAxon Polarizability24.1 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB05245

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB05245

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB05245 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    390017 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Silver_slifadiazine NuGOwiki Link

    HMDB15610 Metagene Link

    HMDB15610 METLIN ID

    Not Available PubChem Compound

    441244 PDB ID

    Not Available ChEBI ID

    9142

    Product: Articaine (hydrochloride)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. Russell AD, Hugo WB: Antimicrobial activity and action of silver. Prog Med Chem. 1994;31:351-70. [PubMed:8029478 ]
    2. Percival SL, Bowler PG, Russell D: Bacterial resistance to silver in wound care. J Hosp Infect. 2005 May;60(1):1-7. [PubMed:15823649 ]
    3. Fox CL Jr, Modak SM: Mechanism of silver sulfadiazine action on burn wound infections. Antimicrob Agents Chemother. 1974 Jun;5(6):582-8. [PubMed:15825409 ]

    PMID: 10903936

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