bumadizone Chemical Properties

Melting point:

117-119℃

Boiling point:

487.4±47.0 °C(Predicted)

Density 

1.227±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Hygroscopic, -20°C Freezer, Under inert atmosphere

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

3.69±0.21(Predicted)

form 

Solid

color 

White to Off-White

Stability:

Hygroscopic

bumadizone Usage And Synthesis

Originator

Eumotol,Byk Gulden,W. Germany,1972

Uses

Bumadizon, is a non-steroidal anti-inflammatory (NSAID) drug.

Definition

ChEBI: A carbohydrazide obtained by formal condensation of one of the carboxy groups from butylmalonic acid with the hydrazino group of 1,2-diphenylhydrazine. Used (as its calcium semihydrate) for treatment of rheumatoid arthritis.

Manufacturing Process

(a) A solution of 22.4 grams of dicyclohexylcarbodiimide in 120 ml of absolute tetrahydrofuran is added dropwise at 5°-10°C in an atmosphere of nitrogen to a solution of 20 grams of n-butylmalonic acid monoethyl ester and 19.6 grams of freshly recrystallized hydrazobenzene in 320 ml of anhydrous tetrahydrofuran. The mixture is then stirred for 15 hr at 25°C in an atmosphere of nitrogen, then the precipitated dicyclohexyl urea is filtered off and the filtrate, after the addition of 3 drops of glacial acetic acid, is evaporated to dryness in vacuo. The residue is dissolved in 1 liter of ether, the ethereal solution is extracted twice with 2 N potassium bicarbonate solution and twice with 2 N hydrochloric acid, whereupon it is washed with water until the washing water is neutral. The ethereal solution is dried over sodium sulfate and concentrated in vacuo. The residue is fractionally distilled under high vacuum whereupon the ester is obtained as a yellow oil. BP 170°C at 0.05 torr vacuum. Crystals which melt at 63°-65°C are obtained from cyclohexane.
(b) A suspension of 7.1 grams of the ester obtained according to (a) in 40 ml of aqueous 0.5 N sodium hydroxide solution is refluxed for 24 hours in an atmosphere of nitrogen. The solution is filtered and traces of hydrazobenzene are removed by extraction with ether. The aqueous solution is made acid to Congo paper at 10°C with concentrated hydrochloric acid, the oil which separates is dissolved in 40 ml of ethyl acetate, the ethyl acetate solution is isolated, and washed neutral with water. The solution is then extracted twice with 36 ml of 0.5 N sodium bicarbonate solution each time.
The separate extracts are made acid to Congo paper with concentr

brand name

Bumaflex;Rheumatol.

Therapeutic Function

Analgesic, Antipyretic, Antirheumatic

World Health Organization (WHO)

Bumadizone, a pyrazolone derivative with antiinflammatory, analgesic and antipyretic activity, was introduced in 1972 for the treatment of rheumatic disorders. As it is structurally related to phenylbutazone it is subjected to rigorously restricted indications by some national regulatory authorities. See WHO comment for phenylbutazone.

bumadizone (3583-64-0)Related Product Information

• Butylmalonic acid
• 1,2-Diphenylhydrazine
• calcium bis[2-butyl-3-(1,2-diphenylhydrazino)-3-oxopropionate]
• bumadizone