3583-64-0 Usage
Uses
Used in Pharmaceutical Industry:
Bumadizone is used as an anti-inflammatory agent for the treatment of rheumatoid arthritis. It helps in reducing inflammation, pain, and stiffness associated with the condition, improving the quality of life for patients suffering from this autoimmune disease.
Additionally, bumadizone is used as a therapeutic agent in the management of other inflammatory conditions, leveraging its NSAID properties to alleviate symptoms and provide relief.
Originator
Eumotol,Byk Gulden,W. Germany,1972
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
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.
Check Digit Verification of cas no
The CAS Registry Mumber 3583-64-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,5,8 and 3 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 3583-64:
(6*3)+(5*5)+(4*8)+(3*3)+(2*6)+(1*4)=100
100 % 10 = 0
So 3583-64-0 is a valid CAS Registry Number.
InChI:InChI=1/C19H22N2O3/c1-2-3-14-17(19(23)24)18(22)21(16-12-8-5-9-13-16)20-15-10-6-4-7-11-15/h4-13,17,20H,2-3,14H2,1H3,(H,23,24)
3583-64-0Relevant academic research and scientific papers
Autoxidation and hydrolysis kinetics of the sodium salt of phenylbutazone in aqueous solution
Fabre,Hussam-Eddine,Lerner,Mandrou
, p. 1709 - 1713 (2007/10/02)
The present investigation offers experimental results concerning the degradation kinetics of the sodium salt of phenylbutazone based on a reliable HPLC procedure. The method allows the simultaneous determination of the parent compound and its main decomposition products. The degradation kinetics at 37° C were compared at pH 7.9 and 10.0 and under oxygen and nitrogen atmospheres. Parallel tests were carried out in the dark and under photolytic conditions for the aforementioned conditions. The influence of traces of iron and a chelating agent of iron on the degradation was studied. At pH 7.9 and pH 10.0 the main degradation products are 3-hydroxy-2-oxohexanoic acid 1,2-diphenylhydrazide and 3-carboxy-2-oxohexanoic acid 1,2-diphenylhydrazide. Azobenzene is formed only at pH 10.0. At pH 7.9, in the dark, the degradation proceeds with a lag phase. In contrast, no lag phase is observed under photolytic conditions. The process of autoxidation and hydrolysis is catalyzed by traces of iron both in the dark and under irradiation conditions. An unexpected increase in the degradation is observed in the presence of iron (III) and EDTA in aerobic conditions and under irradiation.
