4-(aminomethyl)benzene-1-sulfonamide

• ChemBase ID: 53526
• Molecular Formular: C7H10N2O2S
• Molecular Mass: 186.2315
• Monoisotopic Mass: 186.04629857
• SMILES: S(=O)(=O)(c1ccc(cc1)CN)N
• Canonical SMILES: NCc1ccc(cc1)S(=O)(=O)N
• InChI: InChI=1S/C7H10N2O2S/c8-5-6-1-3-7(4-2-6)12(9,10)11/h1-4H,5,8H2,(H2,9,10,11)
• InChIKey: TYMRLRRVMHJFTF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(aminomethyl)benzene-1-sulfonamide
• IUPAC Traditional name: emilene; 4-(aminomethyl)benzene-1-sulfonamide
• Synonyms: 4-Aminomethylbenzenesulfonamide; 4-(Aminomethyl)benzenesulfonamide; Mafenide; 4-Homosulfanilamide; Homosul; Sulfabenzamine; Sulfamylon; Mafenide

Database IDs

• CAS Number: 138-39-6
• MDL Number: MFCD00072084
• PubChem SID: 162058289
• PubChem CID: 3998
• ATC CODE: D06BA03
• CHEMBL: 419
• Chemspider ID: 3858
• KEGG ID: D02351
• Unique Ingredient Identifier: 58447S8P4L
• Wikipedia Title: Mafenide

CALCULATED PROPERTIES

• Acid pKa: 10.268118
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -3.2564728
• LogD (pH = 7.4): -2.1509197
• Log P: -0.54320914
• Molar Refractivity: 46.6893 cm^3
• Polarizability: 18.980124 Å^3
• Polar Surface Area: 86.18 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Admin Routes: Topical
• Mechanism of Action: Folic acid biosynthesis antagonist

Product Information

• Purity: 95+%
• Application(s): Antiseptic; Used as an antibacterial agent in treatment of second- and third-degree burns

REFERENCES

• Miller, E. et al., J.A.C.S., 1940, 62, 2099, (synth)
• Bergeim, F.H. et al., J.A.C.S., 1944, 66, 1459, (synth)
• Japan. Pat., 1949, 177 844; CA, 45, 9404, (manuf)
• Momose, T. et al., Yakugaku Zasshi, 1950, 70, 14, (cryst struct)
• Chang, Y.-T. et al., CA, 1953, 47, 7103, (tox)
• Maschka, A. et al., Monatsh. Chem., 1954, 85, 168, (uv)
• Tanaka, Y. et al., Chem. Pharm. Bull., 1965, 13, 399, (ir)
• Meyer-Dulheuer, K.H. et al., Pharm. Ztg., 1965, 110
• Rakoczy, R. et al., J. Med. Chem., 1967, 10, 273, (salts)
• Chatterjee, C. et al., Acta Cryst. B, 1981, 3, 1835, (cryst struct)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 727, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 179
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MAC000