4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidindion

Bezeichnung:4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidindion

CAS-Nr129-20-4

Englisch Name:OXYPHENYL BUTAZONE

CBNumberCB2133346

SummenformelC19H20N2O3

Molgewicht324.37

MOL-Datei129-20-4.mol

Synonyma

Oxyphenbutazon

4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidindion

4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidindion physikalisch-chemischer Eigenschaften

Schmelzpunkt	109-111°C
Siedepunkt	462.71°C (rough estimate)
Dichte	1.2118 (rough estimate)
Brechungsindex	1.6140 (estimate)
storage temp.	-20°C
Löslichkeit	DMSO: soluble10mg/mL, clear
pka	pKa 4.7/10.0±0.2(H2O,t =25,Iundefined) (Uncertain)
Aggregatzustand	powder
Farbe	white to brown
Wasserlöslichkeit	20mg/L(room temperature)
Stabilität	Hygroscopic
CAS Datenbank	129-20-4(CAS DataBase Reference)
IARC	3 (Vol. 13, Sup 7) 1987
EPA chemische Informationen	3,5-Pyrazolidinedione, 4-butyl-1-(4-hydroxyphenyl)-2-phenyl- (129-20-4)

Sicherheit

Kennzeichnung gefährlicher	Xn,N
R-Sätze:	22-50
S-Sätze:	61
RIDADR	UN 3077 9 / PGIII
WGK Germany	3
Giftige Stoffe Daten	129-20-4(Hazardous Substances Data)

Gefahreninformationscode (GHS)

OXYPHENYL BUTAZONE Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
Light Beige Solid
Originator
Tanderil,Geigy,UK,1960
Verwenden
Anti-inflammatory;Cyclooxygenase inhibito
Indications
Oxyphenbutazone (Oxalid, Tandearil) is the principal uricosuric metabolite of phenylbutazone. It has the same indications and toxicities as phenylbutazone.
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 Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following asso iation with blood dyscrasis and Stevens-Johnson syndrome.
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.
Trademarks
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
Weltgesundheitsorganisation (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.
Allgemeine Beschreibung
Oxyphenbutazone is a derivative compound of phenylbutazone. Oxyphenbutazone is one of the metabolites formed in the liver following administration of phenylbutazone. Given orally it causes fewer gastrointestinal adverse effects than phenylbutazone and is used at 300 – 400 mg/d for the same indications as the parent drug.
Biochem/physiol Actions
Oxyphenbutazone is a non-steroid anti inflammatory; anti Mycobacterium tuberculosis agent. Oxyphenbutazone is known to cause inflammatory effects on tissues. Oxyphenbutazone, as a drug, decreases cellular exudates, without involving the pituitary-adrenal axis or the immunity response. Though the drug delivers a number of side effects, it is considered to be less toxic than phenylbutazone, due to decreased rate of intestinal absorption.
Clinical Use
Oxyphenbutazone is a nonsteroidal anti-inflammatory drug, which was used by oral, rectal, or topical administration (400 - 600 mg/d) for the acute treatment of ankylosing spondylitis, chronic polyarthritis, and gout. Because of a high incidence of severe side effects including disturbances of the hematopoietic system like agranulocytosis and aplastic anemia the compound is no longer used. Oxyphenbutazone is a metabolite of phenylbutazone.

OXYPHENYL BUTAZONE Upstream-Materialien And Downstream Produkte

4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidindion Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

129-20-4, OXYPHENYL BUTAZONE Verwandte Suche:

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