Silver sulfadiazine

Base Information

• Chemical Name: Silver sulfadiazine
• CAS No.: 22199-08-2
• Molecular Formula: C10H9AgN4O2S
• Molecular Weight: 357.141
• Hs Code.: 2935904000
• European Community (EC) Number: 244-834-5
• Wikipedia: Silver_sulfadiazine
• Mol file: 22199-08-2.mol

Synonyms:Silver,(4-amino-N-2-pyrimidinylbenzenesulfonamidato-NN,O1)-;Sulfanilamide,N1-2-pyrimidinyl-, monosilver(1+) salt (8CI);Benzenesulfonamide,4-amino-N-2-pyrimidinyl-, silver complex;Dermazin;Flamazine;Flammazine;Geben;NSC 625324;Silvadene;Silver 2-sulfanilamidopyrimidine;Silverol;Sulfadiazine silver;

Chemical Property of Silver sulfadiazine

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 1.28E-10mmHg at 25°C
• Melting Point: 285 °C (dec.)(lit.)
• Boiling Point: 512.6 °C at 760 mmHg
• Flash Point: 263.8 °C
• PSA: 94.32000
• Density: 1.496g/cm3
• LogP: 3.11490
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 358.97319
• Heavy Atom Count: 18
• Complexity: 354

Purity/Quality:

99%, ^*data from raw suppliers

Silver sulfadiazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CN=C(N=C1)[NH2+]S(=[OH+])(=O)C2=CC=C(C=C2)N.[Ag+]
• Recent ClinicalTrials: SWC for Treatment of Superficial Partial-Thickness Burns
• Recent EU Clinical Trials: A Phase II/III Adaptive, Seamless, Prospective, Randomized, Controlled, Parallel, Open Multicenter Study to Assess the Safety and Efficacy of Kék Lukács Ointment Compared to Standard Silver Sulfadiazine (Dermazin?, SSD) Therapy in the Wound Healing of Patients With Partial Thickness (Second-Degree) Burns
• Uses: Indicated as an adjunct for the prevention and treatment of wound sepsis in patients with second- and third-degree burns. Coordination compound. Antibacterial Silver(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.
• Indications: Silver sulfadiazine (Silvadene, SSD) is a synthetic agent that combines the beneficial properties of silver nitrate and sulfonamides. It acts upon the cell membrane and cell wall. It is used primarily as an adjunct in the prevention and treatment of wound sepsis in patients with second- and third-degree burns and for wound care of chronic ulcers. It is bactericidal against many gram-positive and gram-negative bacteria as well as C. albicans and is reasonably effective against P. aeruginosa and S. aureus. Bacteria susceptible to sulfadiazine but resistant to silver nitrate, as well as those sensitive to silver nitrate but resistant to sulfadiazine, have shown good response to silver sulfadiazine. It does not stain, is unlikely to produce electrolyte imbalance, and does not cause systemic acidosis. Some patients note a stinging sensation on application, and because this compound can be absorbed, systemic sulfonamide reactions similar to those caused by sulfonamides may occur.
• Clinical Use: The silver salt of sulfadiazine applied in a water-misciblecream base has proved to be an effective topical antimicrobialagent, especially against Pseudomonas spp. This is particularlysignificant in burn therapy because pseudomonadsare often responsible for failures in therapy. The salt is onlyslightly soluble and does not penetrate the cell wall butacts on the external cell structure. Studies using radioactivesilver have shown essentially no absorption into body fluids.Sulfadiazine levels in the serum were about 0.5 to2 mg/100 mL.This preparation is reported to be easier to use thanother standard burn treatments, such as application offreshly prepared dilute silver nitrate solutions or mafenideointment.

Technology Process of Silver sulfadiazine

There total 14 articles about Silver sulfadiazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

silver (7440-22-4) + poly[{μ3-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)] (547-32-0) → silver sulfadiazine (22199-08-2)

Guidance literature:

With sodium nitrate; nitric acid; In water; for 0.1h; Electrochemical reaction; Green chemistry;

DOI:10.1039/c9ra04504j

Reference yield:

AgC10H9N4O2S*2benzylamine → benzylamine (100-46-9) + silver sulfadiazine (22199-08-2)

Guidance literature:

With water;

Reference yield:

AgC10H9N4O2S*2ethylamine → ethylamine (75-04-7,85404-22-4) + silver sulfadiazine (22199-08-2)

Guidance literature:

With water;

upstream raw materials:

sulfadiazine

silver

poly[{μ₃-4-[(pyrimidin-2-ylazanidyl)sulfonyl]aniline}sodium(I)]

Downstream raw materials:

sulfadiazine

ganciclovir methyl silver sulphadiazine

bis(μ-4-amino-N-2-pyrimidinylbenzenesulfonamidato-N,N')-dichlorobis(tributylphosphane)dipalladium(II)

Refernces

• 1、 -. "Intraoral medicament delivery and procedure". . . Retrieved 2008/06/13.