Silver sulfadiazine (T3D3068)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-21 20:29:00 UTC
Update Date2014-12-24 20:25:56 UTC
Accession NumberT3D3068
Identification
Common NameSilver sulfadiazine
ClassSmall Molecule
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.
Compound Type
  • Amide
  • Amine
  • Anti-Bacterial Agent
  • Anti-Infective Agent, Local
  • Antibiotic, Topical
  • Drug
  • Metabolite
  • Organic Compound
  • Sulfonamide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Dermazin
Flamazine
Silvadene
Silver sulfadiazinate
Silver sulphadiazine
Silverol
SSD
Sulfadiazine silver
Sulfadiazine silver salt
Thermazene
Chemical FormulaC10H9AgN4O2S
Average Molecular Mass357.137 g/mol
Monoisotopic Mass355.950 g/mol
CAS Registry Number22199-08-2
IUPAC Namesilver(1+) ion 4-{[(pyrimidin-2-yl)azanidyl]sulfonyl}aniline
Traditional Namesilver(1+) ion sulfadiazinate
SMILES[Ag+].NC1=CC=C(C=C1)S(=O)(=O)[N-]C1=NC=CC=N1
InChI IdentifierInChI=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
Description 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
Substituents
  • 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 Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point285°C
Boiling PointNot Available
Solubility7.87e+00 g/L
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.87 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.4 m³·mol⁻¹ChemAxon
Polarizability24.1 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-7691000000-b8839be77eb55e7132fd2017-08-28View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0938000000-be4604140a2bd05885442017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ac0-3892000000-8b82e3b0d3290ae678902017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0300-9500000000-b24ad6397d8c0c6084d52017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-c97de297287bfe6e8b452017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1409000000-b4bb7f26db83fdefa31d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6x-9000000000-090eb04dca3a859505e62017-09-01View Spectrum
Toxicity Profile
Route of ExposureVery limited penetration through the skin. Only when applied to very large area burns is absorption into the body generally an issue.
Mechanism of ToxicityStudies 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.
MetabolismThe degradation of sulfonamides has two different pathways: the N-acetylation pathway which is genetically determined and saturable, and the cytochrome P450 pathway which produces toxic hydroxylamine metabolites "detoxified" by glutathione. (1)
Toxicity ValuesLD50: 10001 mg/kg (oral, rat)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesIndicated as an adjunct for the prevention and treatment of wound sepsis in patients with second- and third-degree burns.
Minimum Risk LevelNot Available
Health EffectsHealth effects include areas of dead skin, red and raised rash on the body, and argyria (Skin discoloration). [Wikipedia]
SymptomsSymptoms include burning sensation. [Wikipedia]
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB05245
HMDB IDHMDB15610
PubChem Compound ID441244
ChEMBL IDCHEMBL1382627
ChemSpider ID390017
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID9142
BioCyc IDNot Available
CTD IDNot Available
Stitch IDSilver sulfadiazine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkSilver_sulfadiazine
References
Synthesis Reference

Charles L. Fox, Jr., Shanta M. Modak, Paul Fox, “Wound dressing comprising silver sulfadiazine incorporated in animal tissue and method of preparation.” U.S. Patent US4599226, issued September, 1977.

MSDSLink
General References
  1. Mathelier-Fusade P, Leynadier F: [Intolerance to sulfonamides in HIV infected subjects. Toxic and allergic origin]. Presse Med. 1993 Oct 2;22(29):1363-5. [8248069 ]
  2. Fox CL Jr, Modak SM: Mechanism of silver sulfadiazine action on burn wound infections. Antimicrob Agents Chemother. 1974 Jun;5(6):582-8. [15825409 ]
  3. Russell AD, Hugo WB: Antimicrobial activity and action of silver. Prog Med Chem. 1994;31:351-70. [8029478 ]
  4. Percival SL, Bowler PG, Russell D: Bacterial resistance to silver in wound care. J Hosp Infect. 2005 May;60(1):1-7. [15823649 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. McDonnell G, Russell AD: Antiseptics and disinfectants: activity, action, and resistance. Clin Microbiol Rev. 1999 Jan;12(1):147-79. [9880479 ]