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Record Information
Version3.6
Creation Date2012-09-06 15:16:52 UTC
Update Date2016-02-11 01:33:35 UTC
HMDB IDHMDB15610
Secondary Accession NumbersNone
Metabolite Identification
Common NameSilver sulfadiazine
DescriptionSilver sulfadiazine is only found in individuals that have used or taken this drug. It is a sulfa derivative topical antibacterial used primarily on second- and third-degree burns. [Wikipedia] Studies utilizing radioactive micronized silver sulfadiazine, electron microscopy, and biochemical techniques have revealed that the mechanism of action of silver sulfadiazine on bacteria differs from silver nitrate and sodium sulfadiazine. Silver sulfadiazine 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 sulfadiazine's 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 sulfhydryl, 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. Sulfadiazine 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
Thumb
Synonyms
ValueSource
FlamazineChEBI
SilvadeneChEBI
Silver sulfadiazinateChEBI
Silver sulfadiazineChEBI
Silver sulphadiazineChEBI
Sulfadiazine silver saltChEBI
Silver;(4-aminophenyl)sulphonyl-pyrimidin-2-ylazanideGenerator
Silver sulfadiazinic acidGenerator
Silver sulphadiazinateGenerator
Silver sulphadiazinic acidGenerator
Sulphadiazine silver saltGenerator
SSDHMDB
Sulfadiazine silverHMDB
Chemical FormulaC10H9AgN4O2S
Average Molecular Weight357.137
Monoisotopic Molecular Weight355.949714262
IUPAC Namesilver(1+) ion 4-{[(pyrimidin-2-yl)azanidyl]sulfonyl}aniline
Traditional Namesilver(1+) ion sulfadiazinate
CAS Registry Number22199-08-2
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 KeyInChIKey=UEJSSZHHYBHCEL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as sulfonylanilines. These are compounds containing an aniline moiety which bears a sulfonyl group at ring position 4.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilines
Direct ParentSulfonylanilines
Alternative Parents
Substituents
  • Sulfonylaniline
  • Benzenesulfonamide
  • Substituted aniline
  • Pyrimidine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic silver salt
  • Organic transition metal salt
  • Organic salt
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Amine
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Infective Agents, Local
  • Antibacterial Agents
  • Sulfonamides
  • Topical Antibiotic
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point285 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.87e+00 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB05245
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB05245
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB05245
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID390017
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSilver_sulfadiazine
NuGOwiki LinkHMDB15610
Metagene LinkHMDB15610
METLIN IDNot Available
PubChem Compound441244
PDB IDNot Available
ChEBI ID9142
References
Synthesis ReferenceNot 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. [8029478 ]
  2. Percival SL, Bowler PG, Russell D: Bacterial resistance to silver in wound care. J Hosp Infect. 2005 May;60(1):1-7. [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. [15825409 ]