55294-15-0

Muzolimine is a structurally novel, pyrazolone diuretic with a high-ceiling profile. It is somewhat slower in onset than furosemide, but has a more prolonged effect, similar to the thiazides. Muzolimine has been shown to be effective in edema of cardiac, hepatic and renal origin. It also appears to be effective as an antihypertensive agent.

Bayer (W. Germany)

Diuretic; antihypertensive.

ChEBI: Muzolimine is a dichlorobenzene.

41 g of α-methyl-3,4-dichlorobenzylhydrazine, dissolved in absolute ethanol, were added dropwise to a solution of 31.8 g of β-amino-β-ethoxyacrylic acid ethyl ester and 1.5 g of p-toluenesulfonic acid in 150 ml of ethanol at room temperature under nitrogen gas. After stirring for 2 hours and standing overnight, the reaction solution was concentrated as far as possible on a rotary evaporator. The residue which remained was dissolved in 2 N sodium hydroxide solution. Any unconverted starting products or by-products were extracted with ether. The aqueous phase was then brought to pH 5 with acetic acid. The oil thereby produced was taken up in methylene chloride and the organic phase was dried over Na2SO4. After evaporating off the solvent, the reaction product crystallized out. It was recrystallized from methanol; melting point 127°C to 129°C; yield 21 g (38.5% of theory).

EDRUL

Diuretic

Reports of neurological adverse effects, including paraesthesiae and paralyses, associated with prolonged use of high dosages of muzolimine, were received shortly after its introduction in 1984.