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 ora ...

blood glucose The blood sugar level, blood sugar concentration, blood glucose level, or glycemia is the measure of glucose concentrated in the blood. The body tightly blood sugar regulation, regulates blood glucose levels as a part of metabolic homeostasis ...

lowering

drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...

used for people with

Type 2 diabetes Type 2 diabetes (T2D), 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 ...

. It is part of the

sulfonylurea Sulfonylureas or sulphonylureas are a class of organic compounds used in medicine and agriculture. The functional group consists of a sulfonyl group (-S(=O)2) with its sulphur atom bonded to a nitrogen atom of a ureylene group (N,N-dehydrourea ...

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 Chemical formula, formula and Chemical structure, structure , which are formally Derivative (chemistry), derived from carbamic acid (). The term includes orga ...

with

ethyl chloroformate Ethyl chloroformate is an organic compound with the chemical formula . It is the ethyl ester of chloroformic acid. It is a colorless, corrosive and highly toxic liquid. It is a reagent used in organic synthesis for the introduction of the ethyl c ...

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