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OXYPHENYL BUTAZONE

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OXYPHENYL BUTAZONE Basic information

Product Name:
OXYPHENYL BUTAZONE
Synonyms:
  • LABOTEST-BB LT00134684
  • OXYPHENYL BUTAZONE
  • 1-(p-Hydroxyphenyl)-2-phenyl-3,5-dioxo-4-N-butylpyrazolidine
  • 1-(p-Hydroxyphenyl)-2-phenyl-4-butyl-3,5-pyrazolidinedione
  • 1-(p-hydroxyphenyl)-2-phenyl-4-butylpyrazolidine-3,5-dione
  • 1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-butylpyrazolidine
  • 1-phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-n-butylpyrazolidine
  • 1-p-hydroxyphenyl-2-phenyl-3,5-dioxo-4-n-butylpyrazolidine
CAS:
129-20-4
MF:
C19H20N2O3
MW:
324.37
EINECS:
204-936-2
Product Categories:
  • Active Pharmaceutical Ingredients
  • Aromatics
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
Mol File:
129-20-4.mol
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OXYPHENYL BUTAZONE Chemical Properties

Melting point:
109-111°C
Boiling point:
462.71°C (rough estimate)
Density 
1.2118 (rough estimate)
refractive index 
1.6140 (estimate)
storage temp. 
-20°C
solubility 
DMSO: soluble10mg/mL, clear
pka
pKa 4.7/10.0±0.2(H2O,t =25,Iundefined) (Uncertain)
form 
powder
color 
white to brown
Water Solubility 
20mg/L(room temperature)
CAS DataBase Reference
129-20-4(CAS DataBase Reference)
IARC
3 (Vol. 13, Sup 7) 1987
EPA Substance Registry System
3,5-Pyrazolidinedione, 4-butyl-1-(4-hydroxyphenyl)-2-phenyl- (129-20-4)
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Safety Information

Hazard Codes 
Xn,N
Risk Statements 
22-50
Safety Statements 
61
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3
Hazardous Substances Data
129-20-4(Hazardous Substances Data)
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OXYPHENYL BUTAZONE Usage And Synthesis

Chemical Properties

Light Beige Solid

Originator

Tanderil,Geigy,UK,1960

Uses

Anti-inflammatory;Cyclooxygenase inhibito

Definition

ChEBI: A metabolite of phenylbutazone obtained by hydroxylation at position 4 of one of the phenyl rings. Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following asso iation with blood dyscrasis and Stevens-Johnson syndrome.

Indications

Oxyphenbutazone (Oxalid, Tandearil) is the principal uricosuric metabolite of phenylbutazone. It has the same indications and toxicities as phenylbutazone.

Manufacturing Process

43.2 parts of n-butyl malonic acid ethyl ester are added to a solution of 4.6 parts of sodium in 92 parts by volume of absolute alcohol. 39 parts of pbenzyloxy hydrazobenzene (MP 88° to 90°C) are added. About two-thirds of the alcohol is distilled off and 92 parts by volume of absolute xylene are added. Without removing the sloping condenser, the mixture is stirred for 12 hours at a bath temperature of 140° to 145°C. It is then cooled to 0° to 5°C, 100 parts of ice are added, the xylene is removed, the aqueous solution is extracted twice with chloroform and made acid to Congo red at 0° to 5°C with 6 N hydrochloric acid.
The precipitate is taken up in chloroform, the solution obtained is washed twice with water, then with saturated salt solution, dried over Na2SO4and evaporated under vacuum (bath temperature 20°C). The residue is recrystallized from alcohol and produces 1-(p-benzyloxyphenyl)-2-phenyl-4-nbutyl-3,5-dioxo-pyrazolidine (C) as tiny white needles which melt at 132° to 133°C.
16.6 parts of (C) are suspended in 166 parts by volume of ethyl acetate and, in the presence of 16.6 parts of Raney nickel, hydrogen is allowed to act at room temperature and atmospheric pressure.
After 6 hours the calculated amount of hydrogen has been taken up. The residue obtained after filtering and evaporating is taken up in benzene and extracted twice with diluted sodium carbonate solution. The alkali extract is then made acid to Congo red with 6 N hydrochloric acid and the precipitate is taken up in ethyl acetate. The solution obtained is washed twice with salt solution, dried with sodium sulfate and evaporated. The residue is recrystallized from ether/petroleum ether. 1-(p-hydroxyphenyl)-2-phenyl-4-n Trade butyl-3,5-dioxo-pyrazolidine melts at 124° to 125°C.

brand name

Tandearil (Novartis);Algi-tandril;Anarreumol-b;Artzone;Buteril;Campozim;Defolgin;Difmedol;Dolo-phlogase;Dolo-tandril;Fibutrox;Gp 40705;Iltazon;Iltoxon;Inflamil;Mindaril;Miyadril;Oflamin;Otone;Oxybutazone;Oxybutol;Oxyperol;Oxyphenbutone;Phlogistol;Phlogont;Phloguran;Pilabutina;Realin;Rheumapax;Segudol;Suganril;Tanal;Tandacot;Teneral;Vefren.

Therapeutic Function

Antiinflammatory

World Health Organization (WHO)

Oxyphenbutazone, a pyrazolone derivative with anti-inflammatory, analgesic and antipyretic activity, was introduced in 1955 for the treatment of rheumatic disorders. It is one of the active metabolites of phenylbutazone and has a similar spectrum of activity including an association with serious and sometimes fatal adverse reactions, notably cases of aplastic anaemia and agranulocytosis. Many national drug regulatory authorities consider that more recently introduced drugs offer a safer alternative for most, if not all, patients requiring antiinflammatory agents. Although oxyphenbutazone has been widely withdrawn it remains available in some countries.

OXYPHENYL BUTAZONESupplier

J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Email
jkinfo@jkchemical.com;market6@jkchemical.com
LGM Pharma
Tel
1-(800)-881-8210
Email
inquiries@lgmpharma.com
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Shanghai TaoSu Biochemical Technology Co., Ltd.
Tel
021-33632979
Email
info@tsbiochem.com
Sigma-Aldrich
Tel
021-61415566- ;
Email
orderCN@merckgroup.com;orderCN@merckgroup.com