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Mafenide

Mafenide structure

CAS No:
138-39-6
Formula:
C7H10N2O2S
Chemical Name:
Mafenide
Synonyms:
Benzenesulfonamide,4-(aminomethyl)-;p-Toluenesulfonamide,α-amino-;4-(Aminomethyl)benzenesulfonamide;α-Amino-p-toluenesulfonamide;Homosulfanilamide;Mafenide;Sulfamylon;Benzamsulfonamide;Homosul;Maphenide;p-(Aminomethyl)benzenesulfonamide;4-Homosulfanilamide;Mesudrin;Mesudin;Ambamide;Neofamid;Septicid;Emilene;Paramenyl;Homonal;Malfamin;Maphenid;Marprontil;4-Sulfamoylbenzylamine;p-Sulfamoylbenzylamine;NSC 34632;4-(Aminosulfonyl)benzylamine;4-(Aminomethyl)benzene-1-sulfonamide
Categories:
Active Pharmaceutical Ingredients > Synthetic Anti-infective Drugs

Description

Mafenide is a sulfonamide-type medication.Target: AntibacterialMafenide is a sulfonamide-type medication. Mafenide works by reducing the bacterial population present in the avascular tissues of burns and permits spontaneous healing of deep partial-thickness burns. It is used to treat severe burns. It is used topically as an adjunctive therapy for second- and third-degree burns. It is bacteriostatic against many gram-positive and gram-negative organisms, including Pseudomonas aeruginosa.

Mafenide is an aromatic amine.|Mafenide is a sulfonamide-type antimicrobial agent used to treat severe burns. It acts by reducing the bacterial population present in the burn tissue and promotes healing of deep burns.|Mafenide is a Methylated Sulfonamide Antibacterial.|A sulfonamide that inhibits the enzyme CARBONIC ANHYDRASE and is used as a topical anti-bacterial agent, especially in burn therapy.

Mafenide Basic Attributes

Molecular Weight：

186.23

Exact Mass：

186.23

EC Number：

205-326-9

UNII：

58447S8P4L

NSC Number：

34632

DSSTox ID：

DTXSID6047860

ATC Code：

D - Dermatologicals

HScode：

2935009090

Characteristics

PSA：

94.6

XLogP3：

-0.80

Density：

1.345±0.06 g/cm3(Predicted)

Melting Point：

151-152 °C

Boiling Point：

382.0±44.0 °C(Predicted)

Flash Point：

184.8±28.4 °C

Refractive Index：

1.602

Water Solubility：

2.09 M

Safety Information

Hazard category：

IRRITANT

Toxicity

Toxicity Summary：

Since mafenide is metabolized to a carbonic anhydrase inhibitor, metabolic acidosis could occur.

Drug Information

Drug Indication：

Indicated for use as an adjunctive topical antimicrobial agent to control bacterial infection when used under moist dressings over meshed autografts on excised burn wounds.|FDA Label

MeSH：

A class of compounds that reduces the secretion of H+ ions by the proximal kidney tubule through inhibition of CARBONIC ANHYDRASES. (See all compounds classified as Carbonic Anhydrase Inhibitors.)|Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)

Absorption：

Mafenide is absorbed through devascularized areas into the systemic circulation following topical administration.|Renal—Metabolite rapidly excreted in urine in high concentrations; however, the parent compound has not been detected in urine.

Metabolism/Metabolites：

Metabolized to a carbonic anhydrase inhibitor.

Mechanism of Action：

The precise mechanism of mafenide is unknown. However, mafenide reduces the bacterial population in the avascular burn tissue and promotes spontaneous heeling of deep burns.

MeSH Entry Terms：

4 Homosulfanilamide

Mafenide Use and Manufacturing

Uses

antibacterial

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:186.23
XLogP3:-0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:186.04629874
Monoisotopic Mass:186.04629874
Topological Polar Surface Area:94.6
Heavy Atom Count:12
Complexity:224
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Benzylamine

Chlorosulfonic acid