DrugBank: Silver sulfadiazine (DB05245)

targets (1)

Identification

Name

Silver sulfadiazine

Accession Number

DB05245

Type

small molecule

Groups

approved

Description

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

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Silver sulfadiazinate
Silver sulphadiazine
SSD
Sulfadiazine silver

Synonyms

Silver sulfadiazinate
Silver sulphadiazine
SSD
Sulfadiazine silver

Salts

Not Available

Brand names

Name	Company
Dermazin
Flamazine
Sildaflo
Silvadene
SSD (1% Silver Sulfadiazine Cream USP)
Thermazene

Brand mixtures

Not Available

Categories

Topical Antibiotic
Anti-Infective Agents, Local
Sulfonamides
Antibacterial Agents

CAS number

22199-08-2

Weight

Average: 357.137
Monoisotopic: 355.949714262

Chemical Formula

C₁₀H₉AgN₄O₂S

InChI Key

InChIKey=UEJSSZHHYBHCEL-UHFFFAOYSA-N

InChI

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

Plain Text

IUPAC Name

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

SMILES

[Ag+].NC1=CC=C(C=C1)S(=O)(=O)[N-]C1=NC=CC=N1

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Benzenesulfonamides
Sulfanilamides

Substructures

Anions
Sulfonyls
Aliphatic and Aryl Amines
Benzene and Derivatives
Benzenesulfonamides
Pyrimidines and Derivatives
Heterocyclic compounds
Aromatic compounds
Sulfanilamides
Sulfonamides
Cyanamides
Anilines
Cations

Pharmacology

Indication

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

Pharmacodynamics

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

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

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

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Acute oral toxicity (LD50) in rat is 10001 mg/kg.

Affected organisms

Yeast and other fungi
Various gram-negative and gram-positive eubacteria

Pathways

Not Available

Pharmacoeconomics

Manufacturers

King pharmaceuticals inc
Dr reddys laboratories louisiana llc
Kendall co lp
Franklin pharmaceuticals inc

Packagers

Dosage forms

Form	Route	Strength
Cream	Topical

Prices

Unit description	Cost	Unit
Silvadene 1% Cream 400 gm Jar	73.48 USD	jar
Silvadene 1% Cream 85 gm Tube	38.47 USD	tube
Silver Sulfadiazine 1% Cream 400 gm Jar	36.48 USD	jar
Silvadene 1% Cream 20 gm Tube	27.94 USD	tube
Silver Sulfadiazine 1% Cream 50 gm Jar	21.99 USD	jar
Silver Sulfadiazine 1% Cream 85 gm Jar	19.99 USD	jar
Silver Sulfadiazine 1% Cream 25 gm Jar	13.99 USD	jar
Silvadene 1% cream	0.93 USD	g
Flamazine 1 % Cream	0.33 USD	g
Ssd af 1% cream	0.21 USD	g
Thermazene 1% cream	0.19 USD	g
Ssd 1% cream	0.12 USD	g
Silver sulfadiazine 1% crm	0.09 USD	g

Patents

Not Available

Properties

State

solid

Melting point

285 oC

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	7.87e+00 g/l	ALOGPS
logP	0.19	ALOGPS
logP	0.39	ChemAxon Molconvert
logS	-1.7	ALOGPS
pKa	0	ChemAxon Molconvert
hydrogen acceptor count	6	ChemAxon Molconvert
hydrogen donor count	1	ChemAxon Molconvert
polar surface area	95.17	ChemAxon Molconvert
rotatable bond count	2	ChemAxon Molconvert
refractivity	63.4	ChemAxon Molconvert
polarizability	24.1	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Fox CL Jr, Modak SM: Mechanism of silver sulfadiazine action on burn wound infections. Antimicrob Agents Chemother. 1974 Jun;5(6):582-8. Pubmed
Russell AD, Hugo WB: Antimicrobial activity and action of silver. Prog Med Chem. 1994;31:351-70. Pubmed
Percival SL, Bowler PG, Russell D: Bacterial resistance to silver in wound care. J Hosp Infect. 2005 May;60(1):1-7. Pubmed

External Links

Resource	Link
KEGG Drug	D00433
PubChem Compound	441244
PubChem Substance	46507881
ChemSpider	390017
ChEBI	9142
ChEMBL	9142
Therapeutic Targets Database	DAP001321
PharmGKB	PA451360
Drug Product Database	323098
RxList	http://www.rxlist.com/cgi/generic/silversulf.htm
Drugs.com	http://www.drugs.com/cdi/silver-sulfadiazine.html
Wikipedia	http://en.wikipedia.org/wiki/Silver_sulfadiazine

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (73.2 KB)

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. DNA Pharmacological action: yes Actions: binder DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes. Gene Sequence: FASTA References: McDonnell G, Russell AD: Antiseptics and disinfectants: activity, action, and resistance. Clin Microbiol Rev. 1999 Jan;12(1):147-79. Pubmed

Targets

1. DNA

Pharmacological action: yes
Actions: binder

DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.

Gene Sequence: FASTA

References:

McDonnell G, Russell AD: Antiseptics and disinfectants: activity, action, and resistance. Clin Microbiol Rev. 1999 Jan;12(1):147-79. Pubmed

Comments

Drug created on October 28, 2007 08:21 / Updated on February 14, 2012 12:11