Chapter 13. Drugs - benzene sulfonamide derivatives

The chemical structure of drugs from this group is based on benzene sulfanilamide:

Classification:

1. Sulfanilamide derivatives ― antibacterial drugs.

2. Sulfonylurea derivatives ― hypoglycemic drugs.

3. Chlorobenzenesulfonic acid amide derivatives ― diuretic drugs.

4. Benzenesulfochloramide derivatives ― drugs-antiseptics.

Medicines ― sulfonilamide derivatives

Name (INN, IUPAC) Chemical structure	Physicochemical properties Application
Benzenesulfochloramide derivatives
Chloramine B Chloramine B Chlordetal Annogen N-chlorobenzenesulfonamide	White or slightly yellowish crystalline powder with a slight chlorine odor; soluble in water, easily soluble in hot water, soluble in ethanol. Antiseptic
Halazone Pantocid Cloritines 4-(dichlorosulfamoyl)benzoic acid	White powder with a chlorine odor; very slightly soluble in water and dilute acids, easily soluble in alkaline solutions and carbonates. Antiseptic
Sulfanilamide derivatives
Sulfanilamide 4-aminobenzenesulfonamide Sulphanilamide Sulfamine 4-aminobenzenesulfonamide	White crystalline powder without odor; slightly soluble in water, easily in boiling water, soluble in diluted hydrochloric acid, alkali solutions and acetone. Antibacterial drug
Sulfacetamide sodium Sodium sulfacetamide Sulfacetamide sodium anhydrous Sulamyd sodium sodium; sodium acetyl(4-aminobenzenesulfonyl)azanide	White crystalline powder; easily soluble in water, very slightly soluble in ethanol. Antibacterial drug
Phthalylsulfathiazole Sulfathalidine Phthalazol Phthalylsulfathiazole 2-[[4-(1,3-thiazol-2-yl sulfamoyl) phenyl]carbamoyl]benzoic acid	White or off-white powder; very slightly soluble in water, soluble in ethanol, easily soluble in sodium hydroxide solution. Antibacterial drug
Co-Trimoxazole Septra Gantrim Sulfamethoxazole-trimethoprim Trimethoprim-sulfamethoxazole 4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide;5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine	Combined drug containing sulfamethoxazole (I) and trimethoprim (II). Antibacterial drug
Sulfonylurea derivatives
Tolbutamide Orinase Artosin Tolbutamid 1-butyl-3-(4-methylphenyl)sulfonylurea	White crystalline powder; Practically insoluble in water, soluble in ethanol, slightly soluble in acetone and chloroform. Antidiabetic drug
Glibenclamide Glyburide Glybenclamide Glynase 5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide	White or almost white fine crystalline powder; practically insoluble in water, slightly soluble in ethanol. Antidiabetic drug
Chlorobenzenesulfonic acid amide derivatives
Furosemide Frusemide Lasix Furosemid 4-chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoic acid	White crystalline powder; practically insoluble in water, soluble in ethanol, slightly soluble in ether. Diuretic
Hydrochlorothiazide Esidrix HCTZ Hypothiazide 6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ6,2,4-benzothiadiazine-7-sulfonamide	White or almost white crystalline powder; very slightly soluble in water, slightly soluble in ethanol, easily soluble in alkali solutions. Diuretic

Sulfanilamide derivatives

Drugs of this group are derivatives of 4-aminobenzenesulfonic (sulfanilic) acid amide (2) -sulfanilamide (3).

Sulfanilic acid (2),

Sulfanilamide (3),

General structural formula of sulfanilamide derivatives.

The combination drug Co-trimoxazole contains a diaminopyrimidine derivative ― trimethoprim (4) and sulfamethoxazole (5). Both exhibit antibacterial activity.

trimethoprim (4)

sulfamethoxazole (5)

Antidiabetic and diuretic benzenesulfonamides

The structure of antidiabetic drugs, derivatives of benzenesulfonylureas is based on the general structural formula:

As diuretics, benzenesulfonamides with an open sulfonamide group (furosemide) are used, as well as disulfamides, derivatives of benzothiadiazine-7-sulfonamide (hydrochlorothiazide) with a chlorine atom as a substituent in the benzene ring.

The presence of the same structures in the chemical structure determines the similarity in the properties and quality control methods of drugs of this group.

General physico-chemical and chemical properties

Medicines from this group are white or yellowish powders. Most of them are slightly soluble in water, soluble in polar solvents, for example, acetone, and slightly soluble in lipophilic solvents (chloroform and ether). Sulfacetamide sodium is highly soluble in water.

The presence of chromophore groups determines the presence of the main absorption zone in the range of 270-280 nm. The UV spectrophotometry method is used in identification and for assay of medicinal substances in drugs.