Bisantrene dihydrochloride Chemical Properties

Melting point:

288-289° (dec)

form 

Solid

color 

Orange crystals

Safety Information

Toxicity

dnd-mus:leu 620 mg/L CNREA8 42,2660,82

Bisantrene dihydrochloride Usage And Synthesis

Description

Bisantrene hydrochloride is a cytostatic useful in the treatment of adult acute, nonlymphocytic leukemia. It is reportedly active against lymphoma, myeloma, bladder, lung and advanced breast cancer, but not small-cell lung cancer, renal cancer, melanoma or refractory adult acute leukemia.

Originator

Lederle (USA)

Uses

Antineoplastic.

Manufacturing Process

A 33.0 g (0.135 mole) of 2-methylthio-2-imidazoline hydroiodide is dissolved in 300 ml of water and treated with 8 ml (0.16 mole) of hydrazine hydrate. The mixture is stirred at room temperature for 20 hours and then taken to dryness under reduced pressure. The residue is dissolved in 250 ml of water and again taken to dryness under reduced pressure. The residue is redissolved in 250 ml of water and added to a mixture of 250 ml of water, 25 ml of concentrated hydrochloric acid and 25 g of silver oxide. The resulting mixture is stirred on a steam bath for 4 hours and then filtered. The filtrate is reduced to dryness under reduced pressure. The residue is dissolved in 300 ml of ethanol and 20 ml of water at the boil, clarified and cooled at -10°C. The precipitate is collected, washed with ethanol and ether and dried at 60°C and then 110°C under reduced pressure. Yield of the 2-hydrazino-2- imidazoline hydrochloride 11.6 g, melting point 177-180°C.
The 2-hydrazino-2-imidazoline monohydrochloride is converted to the dihydrochloride by treatment with ethanol and concentrated hydrochloric acid. A suspension of 3.46 g of the 2-hydrazino-2-imidazoline dihydrochloride and 2.34 g of 9,10-anthracenedicarboxaldehyde in 100 ml of ethanol is stirred and heated under reflux for two hours. The mixture is cooled and the solid is collected and washed with ethanol giving the desired product as a crystalline orange solid, m.p. 288-289°C (dec.).

brand name

Zantrene

Therapeutic Function

Antineoplastic

Safety Profile

Mutation data reported. Whenheated to decomposition it emits toxic fumes of NOx andHCl.

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