Silver Sulfadiazine

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Cat Number

API22199082

CAS Number

22199-08-2

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CAS Number

22199-08-2

EINECS

244-834-5

Storage

Store at 2-8°C

Synonyms

Sulfadiazine silver salt; Flamazine; Silver sulphadiazine; Silvadene; Dermazin; Thermazene; Sulfadiazine, silver

Molecular Formula

C10H9AgN4O2S

Molecular Weight

357.14

Smiles

C1=CN=C(N=C1)[N-]S(=O)(=O)C2=CC=C(C=C2)N.[Ag+]

Appearance

White to off-white solid powder

Melting Point

285°C (dec.) (lit.)

Boiling Point

512.6°C at 760 mmHg

Relative Density

1.496

General Description

Silver sulfadiazine is a silver salt of the sulfonamide antibiotic sulfadiazine, with a silver ion replacing the hydrogen in the sulfonamide group. Its chemical structure is 4-amino-N-(2-pyrimidinyl)benzenesulfonamide silver salt. Silver sulfadiazine is a white to off-white powder, practically insoluble in water but soluble in ammonia. It is a topical antimicrobial agent.

Mechanism of Action

Silver sulfadiazine acts through two mechanisms: the sulfadiazine moiety inhibits bacterial folic acid synthesis by competing with para-aminobenzoic acid (PABA), while the silver ion binds to bacterial DNA and proteins, disrupting cell wall synthesis and membrane permeability. The combination provides synergistic activity against a wide range of gram-positive and gram-negative organisms.

Application

Silver sulfadiazine is indicated for the prevention and treatment of infection in burn wounds and for the management of other skin infections. It is effective in reducing bacterial colonization and promoting wound healing. The drug is particularly useful for the treatment of Pseudomonas aeruginosa infections in burn patients.

TEMPO‑oxidized bacterial cellulose (TOBC) was impregnated with silver sulfadiazine (AgSD) to form nanocomposite membranes. The membranes showed AgSD‑dependent antibacterial activity against Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli, with improved crystallinity. The composite membrane is a promising candidate for wound dressings and tissue engineering scaffolds.

Fig. 1 Synthesis of Folic acid and sulfonamide action site. (Khattak S, et al., 2021)

References

Khattak S, et al. Permeation of Silver Sulfadiazine Into TEMPO-Oxidized Bacterial Cellulose as an Antibacterial Agent. Front Bioeng Biotechnol. 2021;8:616467.

A screen of FDA-approved drugs for activity against 72-hour-established Pseudomonas aeruginosa biofilms identified zinc pyrithione, which also reduced Acinetobacter baumannii and Staphylococcus aureus biofilm-associated bacteria. Zinc pyrithione showed additive effects with silver sulfadiazine in an ointment formulation and improved clearance of all three pathogens in a murine wound infection model. This combination may provide an improved topical therapeutic option for wound infections.

Fig. 2 Antibiofilm effects of zinc pyrithione and silver sulfadiazine individually and in combination against S. aureus, A. baumannii, and P. aeruginosa. (Blanchard C, et al., 2016)

References

Blanchard C, et al. Zinc Pyrithione Improves the Antibacterial Activity of Silver Sulfadiazine Ointment. mSphere. 2016;1(5):e00194-16.

Does Silver Sulfadiazine require protection from light and heat during storage?

Yes, it is photosensitive and thermolabile. Light causes photodegradation and heat accelerates silver ion reduction and discoloration. Store in light-resistant containers at 2-8°C.

Is Silver Sulfadiazine stable in topical cream formulations?

Creams are stable when protected from light and stored under refrigeration.

What is the recommended packaging for Silver Sulfadiazine to prevent degradation?

Use amber glass or opaque containers with tight closures. Avoid metal containers that may react with silver ions.

How is the impurity silver oxide (a reduction product) monitored?

Silver content and related impurities are quantified using atomic absorption or ICP-MS, ensuring they remain within pharmacopoeial specifications.