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Silver, [4-amino-N-(2-pyrimidinyl-kappaN1)benzenesulfonamidato-kappaO]-

HCID 5459124
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Basic information

CAS
22199-08-2
Standard SMILES
Nc1ccc(S(=O)(=O)[N-]c2ncccn2)cc1.[Ag+]
InChIKey
UEJSSZHHYBHCEL-UHFFFAOYSA-N
Molecular formula
C10H9AgN4O2S
Average molar mass
357.14 g/mol
Monoisotopic mass
355.94971

Overview

Silver sulfadiazine is a sulfa derivative topical antibacterial used primarily on second- and third-degree burns.

Names & identifiers

Preferred name
Silver, [4-amino-N-(2-pyrimidinyl-kappaN1)benzenesulfonamidato-kappaO]-
IUPAC
silver (4-aminophenyl)sulfonyl-pyrimidin-2-ylazanide
English name
Silver sulfadiazine
Molecular formula
C10H9AgN4O2S
Molecular weight
357.14

Names & synonyms

NSC625324Silver,O1)-Silver, [4-amino-N-(2-pyrimidinyl-.kappa.N1)benzenesulfonamidato-.kappa.O]-Sulfadiazine silverSilvadeneHY-B1497Sulfanilamide, monosilver(1+) saltCS-0013217Silver, [4-amino-N-(2-pyrimidinyl-.kappa.N1) benzenesulfonamidato-.kappa.O]-SILVER SULPHADIAZINEsilvadeneflamazineSULFADIAZINE SILVER
Show more names
SILVER(I) SULFADIAZINESD-AggebenDermazindermazine

Database identifiers

CAS
22199-08-2
PubChem CID
5459124

Properties

Computed structural properties

Topological polar surface area
95.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
6
Rotatable bonds
1
Heavy atoms
18
Formal charge
0
Complexity
354

Physicochemical properties

Melting point
285 °C · 285 °C (dec.)(lit.)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
DMSO (Slightly, Heated), Methanol (Slightly)
form
powder
color
White to Off-White
Merck
14 · 14,8903
Stability
Stable. Incompatible with strong oxidizing agents.
Major Application
PEM fuel cellsmaterial synthesis precursor
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
InChIKey
UEJSSZHHYBHCEL-UHFFFAOYSA-N
SMILES
Nc1ccc(cc1)S(=O)(=O)N([Ag])c2ncccn2
CAS DataBase Reference
22199 · 22199-08-2(CAS DataBase Reference)
FDA UNII
46 JY43EJR · W46JY43EJR
NCI Drug Dictionary
Silvadene
ATC code
6 BA01,D06BA51 · D06BA01,D06BA51

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
2
rtecs
WP1950000
hs_code
2935904000
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36
hazard_class
IRRITANT
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319
Precautionary statements
P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Chemistry & industry

Pharmacology

Pharmacodynamics · 1 item

Silver sulfadiazine has broad antimicrobial activity. It is bactericidal for many gram- negative and gram-positive bacteria as well as being effective against yeast. Silver sulfadiazine is not a carbonic anhydrase inhibitor and may be useful in situations where such agents are contraindicated.

Mechanism of Action · 1 item

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.

Absorption, Distribution and ExcretionVery limited penetration through the skin. Only when applied to very large area burns is absorption into the body generally an issue.
Applications · 3 items

UsesCoordination compound. Antibacterial

UsesSilver(I) sulfadiazine (AgSD) is popularly used for treating second-degree burn wounds as it acts as an antimicrobial agent and prevents infections. Silver sulfadiazine-impregnated polyurethane (PU) foam, chitosan/chondroitin sulfate films may be used for wound dressing.

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

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319
Precautionary statements
264 · P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36
WGK Germany
2 · 2
RTECS
1950000 · WP1950000
HazardClass
IRRITANT
HS Code
2935904000 · 2935904000
Storage Class
11 · 11 - Combustible Solids

Additional notes

DefinitionChEBI: Silver(1+) sulfadiazinate is a silver salt, a sulfonamidate and a member of pyrimidines. It has a role as an antimicrobial agent and an antibacterial drug. It contains a sulfadiazinate.