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Record Information
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2018-05-20 20:21:02 UTC
Secondary Accession Numbers
  • HMDB15610
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.
Silver sulfadiazinateChEBI
Silver sulphadiazineChEBI
Sulfadiazine silver saltChEBI
Silver sulfadiazinic acidGenerator
Silver sulphadiazinateGenerator
Silver sulphadiazinic acidGenerator
Sulphadiazine silver saltGenerator
Sulfadiazine silverHMDB
Solvay brand OF silver sulfadiazineMeSH
aldo Brand OF silver sulfadiazineMeSH
Par brand 1 OF silver sulfadiazineMeSH
Sulfadiazine, silverMeSH
Rhône-poulenc rorer brand OF silver sulfadiazineMeSH
Silver sulfafdiazineMeSH
Sulfafdiazine, silverMeSH
Zenith brand OF silver sulfadiazineMeSH
medphano Brand OF silver sulfadiazineMeSH
Abbott brand OF silver sulfadiazineMeSH
Major brand OF silver sulfadiazineMeSH
Monarch brand OF silver sulfadiazineMeSH
Par brand 2 OF silver sulfadiazineMeSH
Par brand 3 OF silver sulfadiazineMeSH
Pharmascience brand OF silver sulfadiazineMeSH
Rhône poulenc rorer brand OF silver sulfadiazineMeSH
Sherwood brand OF silver sulfadiazineMeSH
Smith and nephew brand OF silver sulfadiazineMeSH
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
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzenesulfonamides
Direct ParentBenzenesulfonamides
Alternative Parents
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • Aniline or substituted anilines
  • Pyrimidine
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Azacycle
  • Organic transition metal salt
  • Amine
  • Organic salt
  • Organic zwitterion
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organosulfur compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic silver salt
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Biological location:


Industrial application:

Physical Properties
Experimental Properties
Melting Point285 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.87 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility7.87 g/LALOGPS
pKa (Strongest Acidic)6.99ChemAxon
pKa (Strongest Basic)2.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area95.17 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.4 m³·mol⁻¹ChemAxon
Polarizability24.1 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-7691000000-b8839be77eb55e7132fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0938000000-be4604140a2bd0588544View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ac0-3892000000-8b82e3b0d3290ae67890View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0300-9500000000-b24ad6397d8c0c6084d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-c97de297287bfe6e8b45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1409000000-b4bb7f26db83fdefa31dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9000000000-090eb04dca3a859505e6View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationNot Available
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB05245 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB05245 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB05245
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID390017
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSilver_sulfadiazine
METLIN IDNot Available
PubChem Compound441244
PDB IDNot Available
ChEBI ID9142
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. [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 ]