| Identification | More | [Name]
Mafenide acetate | [CAS]
13009-99-9 | [Synonyms]
4-(AMINOMETHYL)-BENZENESULFOAMIDE MONOACETATE
4-(AMINOMETHYL)BENZENESULFONAMIDE ACETATE
4-HOMOSULFANILAMIDE ACETATE
4-HOMOSULFANILAMIDE ACETATE SALT
ALPHA-AMINO-P-TOLUENSULFONAMIDE MONOACETATE
MAFENAMIDE ACETATE
MAFENIDE
MAFENIDE ACETATE
MAFENIDE ACETATE SALT
MARFANIL
MARFANIL ACETATE SALT
P-(AMINOMETHYL) BENZENESULFONAMIDE ACETATE
P-AMINOMETHYLBENZENESULFONAMIDE ACETATE SALT
4-(aminomethyl)benzenesulfonamidemonoacetate
4-(aminomethyl)-benzenesulfonamidmonoacetate
alpha-amino-p-toluenesulfonamidmonoacetate
mafatate
maphenideacetate
alpha-aminotoluene-4-sulphonamide monoacetate
Mafenidine Acetate | [EINECS(EC#)]
235-855-0 | [Molecular Formula]
C9H14N2O4S | [MDL Number]
MFCD00072089 | [Molecular Weight]
246.28 | [MOL File]
13009-99-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline Solid | [Melting point ]
151-152°C | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
DMSO: soluble1mg/mL | [form ]
Solid | [color ]
white | [Usage]
Antibacterial | [InChI]
InChI=1S/C7H10N2O2S.C2H4O2/c8-5-6-1-3-7(4-2-6)12(9,10)11;1-2(3)4/h1-4H,5,8H2,(H2,9,10,11);1H3,(H,3,4) | [InChIKey]
UILOTUUZKGTYFQ-UHFFFAOYSA-N | [SMILES]
C1(=CC=C(CN)C=C1)S(=O)(=O)N.C(=O)(O)C | [CAS DataBase Reference]
13009-99-9(CAS DataBase Reference) |
| Safety Data | Back Directory | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
2935904000 | [Storage Class]
11 - Combustible Solids | [Toxicity]
LD50 in rats, mice (mg/kg): 2040, 1580 i.v. (Skulan, Hoppe) |
| Hazard Information | Back Directory | [Description]
Mafenide Acetate, also known sulfamylon acetate, is a topical sulphonamide antimicrobial agent with activity against a wide range of microorganisms commonly associated with burn wound infections, including Pseudomonas aeruginosa and Staphylococcus aureus. It is primarily used for the prevention and treatment of burn wound infections. As a carbonic anhydrase inhibitor, sulfamylon acetate may cause metabolic acidosis and peripheral vasodilation. Therefore, its concomitant use with hyperbaric oxygen therapy should be carefully assessed. In burn patients requiring hyperbaric oxygen therapy, silver sulfadiazine may be considered as an alternative topical antimicrobial agent. | [Chemical Properties]
Mafenide acetate, USP is a white, crystalline powder which is freely soluble in water. | [Originator]
Sulfamylon,Winthrop,US,1949 | [Uses]
Sulfamylon acetate is used in the treatment of burn wound infections caused by Pseudomonas aeruginosa and other susceptible organisms. | [Definition]
ChEBI: Mafenide acetate is a carboxylic acid. | [Manufacturing Process]
For the preparation of mafenide 50 g of acetylbenzylamine are introduced
while stirring into 150 cc of chlorosulfonic acid, whereby the temperature is
kept below 40°C by external cooling. After several hours' storing at ordinary temperature the mixture is heated for 1 hour in the boiling water-bath and
after cooling, poured on to ice. Thereupon the 4-acetylaminoethylbenzenesulfonic acid chloride precipitates at first in an oily form, but solidifies
after short stirring to crystals. The product sucked off and washed with cold
water is introduced into a 10% aqueous ammonia solution. Thereby
dissolution takes place while heating and after a short time the 4-
acetylaminomethyl-benzenesulfonic acid amide precipitates in a crystalline
form. After heating to 70°C for 30 minutes the solution is cooled, filtered with
suction and washed out. The product is obtained when recrystallized from
water or dilute alcohol in colorless crystals melting at 177%. It is readily
soluble in warm water, extremely readily soluble in dilute sodium hydroxide
solution. | [Brand name]
Sulfamylon (Sterling Winthrop). | [Therapeutic Function]
Antibacterial | [General Description]
4-(Aminomethyl)benzenesulfonamide acetate (Sulfamylon)is a homologue of the sulfanilamide molecule. It is not atrue sulfanilamide-type compound, as it is not inhibited byPABA. Its antibacterial action involves a mechanism thatdiffers from that of true sulfanilamide-type compounds.
This compound is particularly effective against Clostridiumwelchii in topical application and was used duringWorld War II by the German army for prophylaxis ofwounds. It is not effective orally. It is currently used aloneor with antibiotics in the treatment of slow-healing, infectedwounds.
Some patients treated for burns with large quantities ofthis drug have developed metabolic acidosis. To overcomethis adverse effect, a series of new organic salts was prepared. The acetate in an ointment base proved to be themost efficacious. | [Biological Activity]
Mafenide is a bacteriostatic antibiotic with a broad activity against Gram positiveGram negative bacteria and Clostridia. Mafenide acetate penetrates eschar and prevents heavy colonization in burn wounds. | [References]
[1] Afshari A, Nguyen L, Kahn SA, et al. The Effective Duration of Antimicrobial Activity of Mafenide Acetate After Reconstitution. J Burn Care Res. 2018;39(5):736–738. https://doi.org/10.1056/NEJM197106102842310.
[2] Haynes BW Jr. Mafenide Acetate in Burn Treatment. N Engl J Med. 1971;284(23):1324. https://doi.org/10.1056/NEJM197106102842310.
[3] Barsoumian A, Sanchez CJ, Mende K, et al. In Vitro Toxicity and Activity of Dakin's Solution, Mafenide Acetate, and Amphotericin B on Filamentous Fungi and Human Cells. J Orthop Trauma. 2013;27(8):428–436. https://doi.org/10.1056/NEJM197106102842310.
[4] Acaban MB, Sarı A, Demirbağ HO, et al. The Effects of Topical Mafenide Acetate Application on Skin Graft Survival in Bacterial Contaminated Wounds. Burns. 2024;50(2):433–443. https://doi.org/10.1056/NEJM197106102842310. |
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