Pharmaceuticals–Some Important Drugs - Fundamentals of Industrial Chemistry: Pharmaceuticals, Polymers, and Business - page 196

several biguanides including clinical studies of dimethylbiguanide, which he
termed “glucophage” for “glucose eater [43].”

NH NH

NH NH

NH H 3 C

N H NH 2

H 2 N H NH 2

H 2 N NH 2 CH 3

Guanidine Biguanide Metformin

Sulfonylureas represent another widely prescribed class of hypoglycemic
agents. Sulfonylureas stimulate insulin release from pancreatic

-cells [44].
They bind to a specific receptor, called the sulfonylurea receptor on the
β

β

-cell surface [45]. Binding of the sulfonylurea increases calcium influx
which in turn triggers insulin release. The structural differences influence
the binding capacity for the pancreatic -cells which can allow for greater

potency and lower doses [46]. Perhaps the most common is glimepiride
(brand name Amaryl ® , Sanofi-Aventis). Tolbutamide, glibenclamide, and
glicazide are other examples. Tolbutamide is considered a first-generation
sulfonyl urea and others depicted are considered second-generation. Notice
that the second-generation sulfonylureas are more lipophilic and this enables
them to more easily penetrate the cell membranes.

β

Sulfonylurea linkage

CH 3

O

O O

S

O

H

H

N

H

Glimepiride

O

O

O

O O

O O

S N

S

H H H H

H 3 C

H 3 C

Glicazide

Tolbutamide

O

O O

S

O

H H

Cl

N
H

O
CH 3

Glibenclamide

Meglitinides are another class of drugs used in the management of Type
2 diabetes. Similar to the sulfonylureas, they bind to the pancreatic -cells,

albeit at a different site, and open the calcium channels. This induces insulin
secretion. Repaglinide (Prandin ® , Novo Nordisk) is an example of the class.

β