Tolazamide is an

oral The word oral may refer to: Relating to the mouth * Relating to the mouth, the first portion of the alimentary canal that primarily receives food and liquid **Oral administration of medicines ** Oral examination (also known as an oral exam or oral ...

blood glucose Glycaemia, also known as blood sugar level, blood sugar concentration, or blood glucose level is the measure of glucose concentrated in the blood of humans or other animals. Approximately 4 grams of glucose, a simple sugar, is present in the blo ...

lowering

drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...

used for people with

Type 2 diabetes Type 2 diabetes, formerly known as adult-onset diabetes, is a form of diabetes mellitus that is characterized by high blood sugar, insulin resistance, and relative lack of insulin. Common symptoms include increased thirst, frequent urination, ...

. It is part of the

sulfonylurea Sulfonylureas (UK: sulphonylurea) are a class of organic compounds used in medicine and agriculture, for example as antidiabetic drugs widely used in the management of diabetes mellitus type 2. They act by increasing insulin release from the beta ...

family (ATC A10BB).

Synthesis

''para''-Toluenesulfonamide is converted to its

carbamate In organic chemistry, a carbamate is a category of organic compounds with the general formula and structure , which are formally derived from carbamic acid (). The term includes organic compounds (e.g., the ester ethyl carbamate), formally o ...

with

ethyl chloroformate Ethyl chloroformate is the ethyl ester of chloroformic acid. It is a reagent used in organic synthesis for the introduction of the ethyl carbamate protecting group and for the formation of carboxylic anhydrides. Preparation Ethyl chloroforma ...

in the presence of a base. Heating that intermediate with 1-amino-

azepane Azepane is the organic compound with the formula (CH2)6NH. It is a colorless liquid. A cyclic secondary amine, it is a precursor to several drugs and pesticides. It is produced by partial hydrogenolysis of hexamethylene diamine. Like many amine ...

leads to the displacement of the ethoxy group and the formation of tolazemide: Azepane proper would lead to 3078-23-4

References

External links

* Potassium channel blockers Benzenesulfonylureas Azepanes p-Tosyl compounds {{gastrointestinal-drug-stub