Mafenide

Base Information

• Chemical Name: Mafenide
• CAS No.: 138-39-6
• Molecular Formula: C7H10N2O2S
• Molecular Weight: 186.235
• Hs Code.: 2935009090
• European Community (EC) Number: 205-326-9
• NSC Number: 34632
• UNII: 58447S8P4L
• DSSTox Substance ID: DTXSID6047860
• Nikkaji Number: J812E
• Wikipedia: Mafenide
• Wikidata: Q3843044
• NCI Thesaurus Code: C61819
• RXCUI: 6572
• Pharos Ligand ID: TKLJJ81FKP8G
• Metabolomics Workbench ID: 67468
• ChEMBL ID: CHEMBL419
• Mol file: 138-39-6.mol

Synonyms:4 Homosulfanilamide;4-Homosulfanilamide;Bensulfamide;Mafenide;Mafenide Acetate;Mafylon;Maphenid;Marfanil;Napaltan;Sulfabenzamine;Sulfamylon

Chemical Property of Mafenide

Chemical Property:

• Melting Point: 177-178℃ (decomposition)
• Boiling Point: 382 °C at 760 mmHg
• PKA: 10.16±0.10(Predicted)
• Flash Point: 184.8 °C
• PSA: 94.56000
• Density: 1.345 g/cm³
• LogP: 2.27410
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 186.04629874
• Heavy Atom Count: 12
• Complexity: 224

Purity/Quality:

97% ^*data from raw suppliers

4-Aminomethylbenzenesulfonamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1CN)S(=O)(=O)N
• Uses: antibacterial
• Therapeutic Function: Antibacterial

Technology Process of Mafenide

There total 24 articles about Mafenide 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: 95.0%

4-cyanobenzenesulfonamide (3119-02-6) → 4-homosulfanilamide (138-39-6)

Guidance literature:

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 4h;

Reference yield:

4‐(azidomethyl)benzenesulfonamide (864528-35-8) → 4-homosulfanilamide (138-39-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 16h;

Reference yield:

N-(4-sulfamoylbenzyl)acetamide (2015-14-7) → 4-homosulfanilamide (138-39-6)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/ja01237a012

upstream raw materials:

4-cyanobenzenesulfonamide

amino-(4-sulfamoyl-phenyl)-acetic acid

N-(4-sulfamoylbenzyl)acetamide

ammonia

Downstream raw materials:

4-[(pyridine-2-thiocarbonylamino)-methyl]-benzenesulfonic acid-(pyridine-2-thiocarbonylamide)

4-(formylamino-methyl)-benzenesulfonic acid amide

3-(4-sulfamoylbenzyl)-2-thioxothiazolidin-4-one

Refernces

Carbonic anhydrase inhibitors. Part 43. Schiff bases derived from aromatic sulfonamides: Towards more specific inhibitors for membrane-bound versus cytosolic isozymes

10.1016/S0223-5234(97)81681-9

The study investigates the development of more specific carbonic anhydrase (CA) inhibitors, focusing on Schiff bases derived from aromatic sulfonamides. The researchers synthesized 21 new Schiff bases using sulfanilamide, homosulfanilamide, and p-aminoethyl-benzenesulfonamide as starting materials, reacting them with various substituted benzene- and heterocyclic aldehydes. These compounds were characterized and tested for their inhibitory effects on three CA isozymes: CA I, CA II, and CA IV. The results showed that several of these new Schiff bases exhibited a modest two-fold selectivity for the membrane-bound CA IV compared to the cytosolic human isozymes CA I and II. This selectivity is attributed to a decreased potency against hCA II relative to classical inhibitors. The study suggests that these compounds could potentially lead to the development of low molecular weight, isozyme-specific CA IV inhibitors, which may have improved therapeutic profiles and fewer side effects.

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