Mafenide Acetate

Mafenide Acetate

Cat Number
API0232117
CAS Number
13009-99-9

For research use only. We do not supply to patients.

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CAS Number
13009-99-9
EINECS
235-855-0
Storage
Store at room temperature
Synonyms
Sulfamilon; RQ6LP6Z0WY; alpha-Amino-p-toluenesulfonamide monoacetate; 4-(Aminomethyl)benzenesulfonamide monoacetate; DTXSID00156334
Molecular Formula
C9H14N2O4S
Molecular Weight
246.29
Smiles
CC(=O)O.C1=CC(=CC=C1CN)S(=O)(=O)N
Appearance
White to off-white crystalline powder
Melting Point
151-152°C
Boiling Point
382.0±44.0°C at 760 mmHg
Relative Density
1.3±0.1
General Description
Mafenide acetate is a synthetic sulfonamide derivative, specifically p-aminomethylbenzenesulfonamide, in which the methylamine group replaces the typical sulfonamide amino group. The acetate salt is formed to enhance stability and reduce local irritation. Unlike other sulfonamides, mafenide is not significantly inactivated by para-aminobenzoic acid (PABA) or pus, and it retains activity in the presence of high bacterial loads and low pH, such as in burn wounds.
Mechanism of Action
Mafenide inhibits bacterial dihydropteroate synthase, blocking folate synthesis. However, its primary mechanism in burned tissue differs: it is a carbonic anhydrase inhibitor, leading to accumulation of carbonic acid and reduction of local pH, which is directly bactericidal. The drug also penetrates eschar effectively, reaching viable tissue. It has broad activity against gram-positive, gram-negative, and anaerobic organisms, including Pseudomonas aeruginosa and Clostridium species.
Application
Mafenide acetate is indicated as adjunctive therapy for second- and third-degree burns to reduce bacterial colonization and prevent sepsis. It is especially useful for burn wounds infected with Pseudomonas aeruginosa or other resistant pathogens. The drug is applied topically. Its major adverse effect is metabolic acidosis due to carbonic anhydrase inhibition (via the acetate-free base, mafenide itself), requiring monitoring of blood pH and electrolytes.

Mafenide acetate‑loaded nanofibrous films were prepared by electrospinning using chitosan and polyvinyl alcohol (PVA) according to a 3² factorial design. All films prevented bacterial penetration regardless of drug content. Incorporation of mafenide acetate enhanced antimicrobial activity against Staphylococcus aureus and Pseudomonas aeruginosa. The authors conclude that chitosan/PVA nanofibrous films are promising wound dressings with protective, healing, and antimicrobial properties.

Fig. 1 Scanning Electron Micrographs of PVA: Chitosan Nanofibers (PC) Containing Mafenide Acetate. (Abbaspour M, <i>et al</i>., 2015) Fig. 1 Scanning Electron Micrographs of PVA: Chitosan Nanofibers (PC) Containing Mafenide Acetate. (Abbaspour M, et al., 2015)

References

  1. Abbaspour M, et al. Evaluation of the Antimicrobial Effect of Chitosan/Polyvinyl Alcohol Electrospun Nanofibers Containing Mafenide Acetate. Jundishapur J Microbiol. 2015;8(10):e24239.

Does Mafenide Acetate require protection from light and moisture during storage?

Yes, it is photosensitive and hygroscopic. Light accelerates discoloration and moisture promotes hydrolysis. Store in light-resistant, tightly sealed containers with desiccant.

What is the recommended storage temperature for Mafenide Acetate?

Store at controlled room temperature (15-25°C). Avoid temperatures above 30°C, which can accelerate decomposition to p-aminobenzenesulfonamide and acetic acid.

Is Mafenide Acetate stable in topical cream formulations?

Yes, when formulated with appropriate preservatives and protected from light.

How is the impurity p-aminobenzenesulfonamide (sulfanilamide) monitored?

This primary hydrolysis product is specifically quantified using a stability-indicating HPLC method, ensuring it remains below pharmacopoeial limits.
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