Guanoxan

Originator

Envacar,Pfizer

The Uses of Guanoxan

Guanoxan is a sympatholytic drug related to Guanethidine (G815000). Guanoxan is used in the treatment of hypertension.

Background

Guanoxan is an antihypertensive agent similar in its mechanism of action to guanethidine; may cause liver damage. Guanoxan was approved in the UK but was withdrawn from the market due to hepatotoxicity.

Definition

ChEBI: Guanoxan is a benzodioxine.

Manufacturing Process

2 Methods of producing of 2-guanidinemethyl-2,3-dihydro-1,4-benzodioxine:
1. 3.3 parts by weight of 2-aminomethyl-1,4-benzodioxane and 2.78 parts by weight of S-methylisothiouronium sulfate were dissolved in 20 parts by volume of water, and the resulting aqueous solution was heated under reflux for 3 h. At the end of this time, the solvent was removed by means of evaporation under reduced pressure and the residue so obtained dissolved in a minimum amount of fresh water and treated with charcoal. Upon filtration, there was obtained a clear filtrate which, on standing, soon afforded pure crystals of di(2-guanidinomethyl-1,4-benzodioxane)sulfate, melting point 204°-205°C.
The base 2-guanidinemethyl-2,3-dihydro-1,4-benzodioxine may be obtained by reaction of di(2-guanidinomethyl-1,4-benzodioxane)sulfate with, for example, sodium hydroxide.
2. o-Dihydroxybenzene reacted with epichlorhydrine in the presence sodium hydroxide and 2-hydroxymethyl-2,3-dihydro-1,4-benzodioxine was obtained. To solution of 2-hydroxymethyl-2,3-dihydro-1,4-benzodioxine thionylchloride was added to give 2-chlormethyl-2,3-dihydro-1,4-benzodioxine.
2-Chloromethyl-2,3-dihydro-1,4-benzodioxine reacted with benzylamine to produced 2-benzylaminomethyl-2,3-dihydro-1,4-benzodioxine, which was reduced at the presence of hydrogen and Pd-C (catalyst) to 2-aminomethyl- 2,3-dihydro-1,4-benzodioxine.
2-Aminomethyl-2,3-dihydro-1,4-benzodioxine was treated by Smethylisothiouronium sulfate and there was produced 2-guanidinemethyl-2,3- dihydro-1,4-benzodioxine.

brand name

Envacar (Pfizer).

Therapeutic Function

Antihypertensive

Metabolism

Not Available