KETOPHENYLBUTAZONE
KETOPHENYLBUTAZONE Basic information
- Product Name:
- KETOPHENYLBUTAZONE
- Synonyms:
-
- keobutane-jade
- ketason
- ketazone
- kpb
- pecnon
- KETOPHENYLBUTAZONE
- 1,2-diphenyl-4-(3’-oxobutyl)-3,5-dioxopyrazolidine
- 1,2-diphenyl-4-(3-oxobutyl)-5-pyrazolidinedione
- CAS:
- 853-34-9
- MF:
- C19H18N2O3
- MW:
- 322.36
- EINECS:
- 212-715-7
- Product Categories:
-
- Aromatics
- Heterocycles
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Mol File:
- 853-34-9.mol
KETOPHENYLBUTAZONE Chemical Properties
- Melting point:
- 115.5-116.5° or 127.5-128.5° depending on cryst form
- Boiling point:
- 460.98°C (rough estimate)
- Density
- 1.2336 (rough estimate)
- refractive index
- 1.6140 (estimate)
- storage temp.
- Refrigerator
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
- form
- Solid
- color
- Off-White to Light Yellow
- Water Solubility
- 174.2mg/L(20 ºC)
KETOPHENYLBUTAZONE Usage And Synthesis
Originator
Chebutan,Bioindustria,Italy,1961
Uses
Antirheumatic.
Definition
ChEBI: A pyrazolidine that is phenylbutazone in which the two methylene hydrogens at postion 3 on the butyl chain are replaced by an oxo group.
Manufacturing Process
(a) 3,3-ethylene dioxyburyl malonic acid diethyl ester: Diethylmalonate is
reacted with methyl vinyl ketone and the resulting oxobutyl diethylmalonate is
reacted with ethylene glycol.
(b) 1,2-diphenyl-4-(3',3'-ethylene dioxybutyl)3,5-dioxopyrazolidine: 274 parts
of (3,3-ethylene dioxybutyl)-malonic acid diethyl ester are dissolved in 100
parts by volume of abs. benzene and 57 parts of sodium ethylate and 184
parts of hydrazobenzene are added. Heat is generated. The reaction mass is
boiled for 15 hours under reflux. After cooling, it is poured into water,
separated and the aqueous part is washed twice with benzene. The benzene
solutions are washed three times with 2N sodium carbonate solution and the
unified aqueous solutions are acidified with 2N hydrochloric acid. The 1,2-
phenyl-4-(3',3'-ethylene dioxybutyl)-3,5-dioxopyrazolidine which precipitates
can be recrystallized from alcohol. Melting point 165°C to 167°C.
(c) 1,2-diphenyl-4-(3'-oxobutyl)-3,5-dioxopyrazolidine: 36.6 parts of 1,2-
diphenyl-4-(3',3'-ethylene dioxybutyl)-3,5-dioxopyrazolidine in 750 parts byvolume of acetone are boiled under reflux for 18 hours with 0.35 part of ptoluene sulfonic acid. The solution is then filtered, 1,500 parts of water are
added and the whole is allowed to stand for 24 hours at 5°C. The 1,2-
diphenyl-4-(3'-oxobutyl)-3,5-dioxopyrazolidine which precipitates is filtered off
under suction and washed with 50% acetone. Melting point from alcohol/water
mixture: 115.5°C to 116.5°C. Sometimes a crystal form is obtained which
melts at 127.5°C to 128.5°C.
brand name
Benjor;Chebutan;Chepirol;Chetazolidin;Chetosol;Copirene;Gammachetone;Hichillos;Kentan-s;Kenta-s;Kenzon r;Ketobutane-jade;Ketofen;Neo-panalgyl;Neufenil;Neuphenyl;Phloguron;Recheton;Reuchetal;Reumo;Tkb;Vintab;Vintop.
Therapeutic Function
Antirheumatic
World Health Organization (WHO)
Kebuzone, a pyrazolone derivative with anti-inflammatory, analgesic and antipyretic activity, was introduced in 1973 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.
Clinical Use
Kebuzone is a nonsteroidal anti-inflammatory drug used for the treatment of acute and chronic pain and inflammation states like musculoskeletal, joint, and soft-tissue disorders. Kebuzone is administered orally, rectally, or intramuscular (up to 1500 mg/d i
KETOPHENYLBUTAZONESupplier
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KETOPHENYLBUTAZONE(853-34-9)Related Product Information
- Phenylbutazone
- N-PHENYL-N'-PROPIONYLHYDRAZINE
- MOFEBUTAZONE
- tribuzone
- 1,2-DIPHENYL-PYRAZOLIDINE-3,5-DIONE
- benzopyrazone
- 1,2-Diphenylhydrazine
- Phenidone
- 1-Phenyl-4-methyl-3-pyrazolidone
- Benzoic acid, 2-(acetyloxy)-, (4-(4,4-dimethyl-3-oxopentyl)-3,5-dioxo- 1,2-diphenyl-4-pyrazolidinyl)methyl ester
- KETOPHENYLBUTAZONE