ContaminantDB: Silver sulfadiazine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (2)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:29:00 UTC

Update Date

2026-05-14 18:13:25 UTC

Accession Number

CHEM002410

Identification

Common Name

Silver sulfadiazine

Class

Small Molecule

Description

Silver 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.

Contaminant Sources

HMDB Contaminants - Urine
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Anti-Bacterial Agent
Anti-Infective Agent, Local
Antibiotic, Topical
Drug
Metabolite
Organic Compound
Sulfonamide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Flamazine	ChEBI
Silvadene	ChEBI
Silver sulfadiazinate	ChEBI
Silver sulphadiazine	ChEBI
Sulfadiazine silver salt	ChEBI
Sulfadiazine silver	Kegg
Silver sulfadiazinic acid	Generator
Silver sulphadiazinate	Generator
Silver sulphadiazinic acid	Generator
Sulphadiazine silver salt	Generator
Sulphadiazine silver	Generator
SSD	HMDB, MeSH
Brandiazin	MeSH
SSD AF	MeSH
Silvederma	MeSH
Solvay brand OF silver sulfadiazine	MeSH
aldo Brand OF silver sulfadiazine	MeSH
Par brand 1 OF silver sulfadiazine	MeSH
Sulfadiazine, silver	MeSH
Sulfargen	MeSH
Dermazin	MeSH
Rhône-poulenc rorer brand OF silver sulfadiazine	MeSH
Silver sulfafdiazine	MeSH
Sulfafdiazine, silver	MeSH
Thermazene	MeSH
Zenith brand OF silver sulfadiazine	MeSH
medphano Brand OF silver sulfadiazine	MeSH
Abbott brand OF silver sulfadiazine	MeSH
Flammazine	MeSH
Major brand OF silver sulfadiazine	MeSH
Monarch brand OF silver sulfadiazine	MeSH
Par brand 2 OF silver sulfadiazine	MeSH
Par brand 3 OF silver sulfadiazine	MeSH
Pharmascience brand OF silver sulfadiazine	MeSH
Rhône poulenc rorer brand OF silver sulfadiazine	MeSH
Sherwood brand OF silver sulfadiazine	MeSH
Sicazine	MeSH
Smith and nephew brand OF silver sulfadiazine	MeSH
Silver sulfadiazine	ChEBI
Silver(1+) sulfadiazinic acid	Generator
Silver(1+) sulphadiazinate	Generator
Silver(1+) sulphadiazinic acid	Generator

Chemical Formula

C₁₀H₉AgN₄O₂S

Average Molecular Mass

357.137 g/mol

Monoisotopic Mass

355.950 g/mol

CAS Registry Number

22199-08-2

IUPAC Name

silver(1+) 4-{[(pyrimidin-2-yl)azanidyl]sulfonyl}aniline

Traditional Name

silver(1+) ion sulfadiazinate

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

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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

silver salt (CHEBI:9142 )
sulfonamidate (CHEBI:9142 )
pyrimidines (CHEBI:9142 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	285°C
Boiling Point	Not Available
Solubility	7.87e+00 g/L

Predicted Properties

Property	Value	Source
Water Solubility	7.87 g/L	ALOGPS
logP	0.19	ALOGPS
logP	0.39	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	6.99	ChemAxon
pKa (Strongest Basic)	2.01	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	95.17 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.4 m³·mol⁻¹	ChemAxon
Polarizability	24.1 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-7691000000-b8839be77eb55e7132fd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0938000000-be4604140a2bd0588544	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ac0-3892000000-8b82e3b0d3290ae67890	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0300-9500000000-b24ad6397d8c0c6084d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-c97de297287bfe6e8b45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1409000000-b4bb7f26db83fdefa31d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9000000000-090eb04dca3a859505e6	Spectrum

Toxicity Profile

Route of Exposure

Very limited penetration through the skin. Only when applied to very large area burns is absorption into the body generally an issue.

Mechanism of Toxicity

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.

Metabolism

The 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 Values

LD50: 10001 mg/kg (oral, rat)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Indicated as an adjunct for the prevention and treatment of wound sepsis in patients with second- and third-degree burns.

Minimum Risk Level

Not Available

Health Effects

Health effects include areas of dead skin, red and raised rash on the body, and argyria (Skin discoloration). [Wikipedia]

Symptoms

Symptoms include burning sensation. [Wikipedia]

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB05245

HMDB ID

HMDB0015610

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Silver_sulfadiazine

Chemspider ID

Not Available

ChEBI ID

9142

PubChem Compound ID

441244

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

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.

MSDS

Link

General References

Not Available

Silver sulfadiazine (CHEM002410)

Structure for CHEM002410: Silver sulfadiazine