Identification

Name
Silver sulfadiazine
Accession Number
DB05245
Type
Small Molecule
Groups
Approved, Vet approved
Description

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

Structure
Thumb
Synonyms
  • Silver sulfadiazinate
  • Silver sulfadiazine
  • Silver sulphadiazine
  • Sulfadiazine silver
  • Sulfadiazine silver salt
Active Moieties
NameKindUNIICASInChI Key
Sulfadiazineunknown0N7609K88968-35-9SEEPANYCNGTZFQ-UHFFFAOYSA-N
Silver cationionic57N7B0K90A14701-21-4FOIXSVOLVBLSDH-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Dermazin Crm 1%Cream1 %TopicalPharmascience Inc1993-12-312016-10-28Canada
Flamazine Crm 1%Cream1 %TopicalSmith & Nephew, Inc.1974-12-31Not applicableCanada
SilvadeneCream10 mg/1gTopicalA-S Medication Solutions1973-11-26Not applicableUs
SilvadeneCream10 mg/1gTopicalA-S Medication Solutions1973-11-262016-05-31Us
SilvadeneCream10 mg/1gTopicalA S Medication Solutions1973-11-26Not applicableUs
SilvadeneCream10 mg/1gTopicalCentral Texas Community Health Centers1973-11-26Not applicableUs
SilvadeneCream10 mg/1gTopicalA S Medication Solutions1973-11-26Not applicableUs
SilvadeneCream10 mg/1gTopicalLake Erie Medical &Surgical Supply Dba Quality Care Products Llc1973-11-26Not applicableUs
SilvadeneCream10 mg/1gTopicalPfizer Laboratories Div Pfizer Inc.1973-11-26Not applicableUs
SilvadeneCream10 mg/1gTopicalPhysicians Total Care, Inc.1973-11-262011-07-31Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Silver SulfadiazineCream10 mg/1gTopicalKeltman Pharmaceuticals Inc.2007-03-10Not applicableUs
Silver SulfadiazineCream10 mg/1gTopicalGreenstone, Llc2018-01-15Not applicableUs
Silver SulfadiazineCream10 g/1000gTopicalLake Erie Medical &Surgical Supply Dba Quality Care Products Llc2012-03-22Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hydrogel AG Silver Antimicrobial Wound DressingGel1 kg/1kgTopicalGentell, Inc.2018-01-01Not applicableUs
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Flamazine CSilver sulfadiazine (10 mg) + Chlorhexidine gluconate (2 mg)CreamTopicalSmith & Nephew, Inc.1987-12-312001-07-01Canada
International/Other Brands
Dermazin / Flamazine / Silvadene / Silverol
Categories
UNII
W46JY43EJR
CAS number
22199-08-2
Weight
Average: 357.137
Monoisotopic: 355.949714262
Chemical Formula
C10H9AgN4O2S
InChI Key
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
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

Pharmacology

Indication

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

Associated Conditions
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.

TargetActionsOrganism
ADNA
binder
Human
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
  • Candida albicans and other yeasts
  • Various gram-negative and gram-positive eubacteria
  • Pseudomonas aeruginosa
  • Staphylococcus aureus
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with Silver sulfadiazine.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Silver sulfadiazine.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Silver sulfadiazine.
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Silver sulfadiazine.
AcarboseThe therapeutic efficacy of Acarbose can be increased when used in combination with Silver sulfadiazine.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Silver sulfadiazine.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be increased when used in combination with Silver sulfadiazine.
AICA ribonucleotideThe therapeutic efficacy of AICA ribonucleotide can be increased when used in combination with Silver sulfadiazine.
AlbiglutideThe therapeutic efficacy of Albiglutide can be increased when used in combination with Silver sulfadiazine.
AlogliptinThe therapeutic efficacy of Alogliptin can be increased when used in combination with Silver sulfadiazine.
Food Interactions
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.

US4599226
General References
  1. 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]
  2. Russell AD, Hugo WB: Antimicrobial activity and action of silver. Prog Med Chem. 1994;31:351-70. [PubMed:8029478]
  3. Percival SL, Bowler PG, Russell D: Bacterial resistance to silver in wound care. J Hosp Infect. 2005 May;60(1):1-7. [PubMed:15823649]
External Links
Human Metabolome Database
HMDB0015610
KEGG Drug
D00433
PubChem Compound
441244
PubChem Substance
46507881
ChemSpider
390017
ChEBI
9142
ChEMBL
CHEMBL1382627
Therapeutic Targets Database
DAP001321
PharmGKB
PA164744951
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Silver_sulfadiazine
ATC Codes
D06BA51 — Silver sulfadiazine, combinationsD06BA01 — Silver sulfadiazineG01AE10 — Combinations of sulfonamides
AHFS Codes
  • 84:04.92 — Miscellaneous Local Anti-infectives
MSDS
Download (73.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
2CompletedTreatmentMinor burns1
4CompletedTreatmentSecond-degree Burn1
4CompletedTreatmentMinor burns1
Not AvailableCompletedTreatmentMinor burns2
Not AvailableUnknown StatusTreatmentIngrown Nail1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Ascend Laboratories LLC
  • BASF Corp.
  • DispenseXpress Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Innoviant Pharmacy Inc.
  • Keltman Pharmaceuticals Inc.
  • King Pharmaceuticals Inc.
  • Monarch Pharmacy
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • Pharmedix
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Quality Care
  • Rebel Distributors Corp.
  • Sanofi-Aventis Inc.
  • Sherwood Medical
  • Stat Rx Usa
  • Tyco Healthcare Group LP
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
CreamTopical
CreamTopical1 %
GelTopical1 kg/1kg
CreamTopical10 g/1000g
CreamTopical10 mg/1g
Prices
Unit descriptionCostUnit
Silvadene 1% Cream 400 gm Jar73.48USD jar
Silvadene 1% Cream 85 gm Tube38.47USD tube
Silver Sulfadiazine 1% Cream 400 gm Jar36.48USD jar
Silvadene 1% Cream 20 gm Tube27.94USD tube
Silver Sulfadiazine 1% Cream 50 gm Jar21.99USD jar
Silver Sulfadiazine 1% Cream 85 gm Jar19.99USD jar
Silver Sulfadiazine 1% Cream 25 gm Jar13.99USD jar
Silvadene 1% cream0.93USD g
Flamazine 1 % Cream0.33USD g
Ssd af 1% cream0.21USD g
Thermazene 1% cream0.19USD g
Ssd 1% cream0.12USD g
Silver sulfadiazine 1% crm0.09USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)285 °CNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.87 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.4 m3·mol-1ChemAxon
Polarizability24.1 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9711
Blood Brain Barrier+0.9438
Caco-2 permeable+0.621
P-glycoprotein substrateNon-substrate0.9127
P-glycoprotein inhibitor INon-inhibitor0.9363
P-glycoprotein inhibitor IINon-inhibitor0.9097
Renal organic cation transporterNon-inhibitor0.8426
CYP450 2C9 substrateNon-substrate0.7881
CYP450 2D6 substrateNon-substrate0.8443
CYP450 3A4 substrateNon-substrate0.7321
CYP450 1A2 substrateNon-inhibitor0.9233
CYP450 2C9 inhibitorNon-inhibitor0.8439
CYP450 2D6 inhibitorNon-inhibitor0.9385
CYP450 2C19 inhibitorNon-inhibitor0.8978
CYP450 3A4 inhibitorNon-inhibitor0.8894
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8721
Ames testNon AMES toxic0.8603
CarcinogenicityNon-carcinogens0.9406
BiodegradationNot ready biodegradable0.9517
Rat acute toxicity2.1559 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9314
hERG inhibition (predictor II)Non-inhibitor0.8823
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Benzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / Aniline and substituted anilines / Pyrimidines and pyrimidine derivatives / Sulfonyls / Organosulfonic acids and derivatives / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organic zwitterions
show 3 more
Substituents
Benzenesulfonamide / Benzenesulfonyl group / Aniline or substituted anilines / Pyrimidine / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Sulfonyl / Heteroaromatic compound / Organoheterocyclic compound / Azacycle
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
silver salt, sulfonamidate, pyrimidines (CHEBI:9142)

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Yes
Actions
Binder
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. [PubMed:9880479]

Drug created on October 28, 2007 08:21 / Updated on October 15, 2018 04:36