Letosteine

Originator

Viscotiol,Carlo Erba,France,1979

Definition

ChEBI: A dicarboxylic acid monoester that is the monoethyl ester of 2-{2-[(carboxymethyl)sulfanyl]ethyl}-1,3-thiazolidine-4-carboxylic acid. A mucolytic used in the treatment of chronic bronchopneumopathies and related conditions.

Manufacturing Process

In an Erlenmeyer flask placed in an ice bath, and under a well-ventilated hood, a solution of 0.1 mol of acrolein in 100 ml of ether was introduced, With the aid of a bromine ampoule, 0.1 mol (= 11 ml) of the ethyl ester of thioglycolic acid containing 0.5 ml of triethylamine was added drop by drop.
One hour after completion of the addition, there was added 0.1 mol (15.6 g) of chlorhydrate of cysteine in alcoholic solution. The chlorhydrate of the expected derivative, which appeared in the form of a thick oil, was precipitated by addition of 0.1 mol (10 g) of potassium acetate in aqueous solution. The abundant precipitate obtained was filtered and washed in water and ether. The product was recrystallized in a minimum of absolute alcohol.

Therapeutic Function

Mucolytic