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Phenylbutazone

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Name

Phenylbutazone

EINECS 200-029-0
CAS No. 50-33-9 Density 1.173 g/cm3
PSA 40.62000 LogP 3.91780
Solubility water: <0.1 g/100 mL at 23.5 °C Melting Point 104-107 °C
Formula C19H20N2O2 Boiling Point 424.9 °C at 760 mmHg
Molecular Weight 308.38 Flash Point 174.3 °C
Transport Information N/A Appearance off-white powder
Safety 36/37/39-26-45-22-53 Risk Codes 36/37/38-20/21/22-42/43-45
Molecular Structure Molecular Structure of 50-33-9 (Phenylbutazone) Hazard Symbols HarmfulXn,ToxicT
Synonyms

1,2-Diphenyl-3,5-dioxo-4-butylpyrazolidine;1,2-Diphenyl-3,5-dioxo-4-n-butylpyrazolidine;1,2-Diphenyl-4-butyl-3,5-pyrazolidinedione;3,5-Dioxo-1,2-diphenyl-4-n-butylpyrazolidine;

Article Data 30

Phenylbutazone Synthetic route

109-65-9

1-bromo-butane

2652-77-9

1,2-diphenylpyrazolidine-3,5-dione

A

50-33-9

Phenylbutazone

B

102886-57-7

4,4-dibutyl-1,2-diphenylpyrazolidine-3,5-dione

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In hexane; acetonitrile at 55℃; for 18h; Inert atmosphere; Cooling with ice;A 85%
B 15%
109-65-9

1-bromo-butane

2652-77-9

1,2-diphenylpyrazolidine-3,5-dione

50-33-9

Phenylbutazone

Conditions
ConditionsYield
With potassium carbonate; sodium iodide In hexane; acetonitrile at 55℃; for 22h; Inert atmosphere; Cooling with ice;78%
With sodium hydroxide
133-08-4

diethyl butylmalonate

122-66-7

diphenyl hydrazine

50-33-9

Phenylbutazone

Conditions
ConditionsYield
Stage #1: diethyl butylmalonate With sodium ethanolate In ethanol at 20℃; Inert atmosphere; Schlenk technique;
Stage #2: diphenyl hydrazine In ethanol for 24h; Reflux; Inert atmosphere; Schlenk technique;
75%
With sodium ethanolate
With sodium ethanolate
2652-77-9

1,2-diphenylpyrazolidine-3,5-dione

71-36-3

butan-1-ol

50-33-9

Phenylbutazone

Conditions
ConditionsYield
With nickel; benzene
133-08-4

diethyl butylmalonate

22293-38-5

1-acetyl-1,2-diphenylhydrazine

50-33-9

Phenylbutazone

Conditions
ConditionsYield
With sodium ethanolate

bromo-butyl-malonyl chloride

122-66-7

diphenyl hydrazine

50-33-9

Phenylbutazone

Conditions
ConditionsYield
With diethyl ether; diethylamine
122-66-7

diphenyl hydrazine

17999-54-1

2-n-butylmalonyl dichloride

50-33-9

Phenylbutazone

Conditions
ConditionsYield
With pyridine; ethanol
hexanoic acid

hexanoic acid

50-33-9

Phenylbutazone

Conditions
ConditionsYield
With sodium hydride; benzene
534-59-8

n-butylmalonic acid

50-33-9

Phenylbutazone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: diethyl ether; bromine / Behandeln einer Loesung des Reaktionsprodukts in Aether mit Phosphor(V)-chlorid
2: diethyl ether; diethylamine
View Scheme
1229645-19-5

C20H23N2O6P

50-33-9

Phenylbutazone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / ethanol; water
2: human placental alkaline phosphatase; magnesium chloride; zinc(II) chloride / 37 °C / pH 7.4 / aq. buffer; Enzymatic reaction
View Scheme

Phenylbutazone Chemical Properties

IUPAC Name: 4-butyl-1,2-diphenylpyrazolidine-3,5-dione 
Empirical Formula: C19H20N2O2
Molecular Weight: 308.3743g/mol
EINECS: 200-029-0 
Structure of 4-Butyl-1,2-diphenyl-3,5-dioxopyrazolidine (CAS NO.50-33-9):

Index of Refraction: 1.59
Molar Refractivity: 88.7 cm3
Molar Volume: 262.7 cm3
Polarizability: 35.16×10-24cm3
Surface Tension: 47.3 dyne/cm
Density: 1.173 g/cm3
Flash Point: 174.3 °C
Enthalpy of Vaporization: 67.94 kJ/mol 
Melting Point: 104-107 °C
Boiling Point: 424.9 °C at 760 mmHg
Vapour Pressure: 2E-07 mmHg at 25°C 
Water Solubility: <0.1 g/100 mL at 23.5 ºC 
Stability: Stable. Incompatible with strong oxidizing agents, strong acids, strong bases. 
Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals  
Canonical SMILES: CCCCC1C(=O)N(N(C1=O)C2=CC=CC=C2)C3=CC=CC=C3
InChI: InChI=1S/C19H20N2O2/c1-2-3-14-17-18(22)20(15-10-6-4-7-11-15)21(19(17)23)16-12-8-5-9-13-16/h4-13,17H,2-3,14H2,1H3
InChIKey: VYMDGNCVAMGZFE-UHFFFAOYSA-N

Phenylbutazone Uses

 4-Butyl-1,2-diphenyl-3,5-dioxopyrazolidine (50-33-9) is a non-steroidal anti-inflammatory compound. An inhibitor of cyclooxygenase that is also a substrate for peroxidation by cyclooxygenase.

Phenylbutazone Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intravenous 100mg/kg (100mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 36, 1969.
dog LD50 intravenous 121mg/kg (121mg/kg) BEHAVIORAL: ANALGESIA Archives Internationales de Pharmacodynamie et de Therapie. Vol. 149, Pg. 571, 1964.
dog LD50 oral 332mg/kg (332mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 265, 1980.
guinea pig LD50 oral 250mg/kg (250mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1207, 1969.
hamster LD50 oral 1260mg/kg (1260mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
mammal (species unspecified) LD50 intraperitoneal 300mg/kg (300mg/kg) BEHAVIORAL: ANALGESIA European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 21, Pg. 277, 1986.
mammal (species unspecified) LD50 oral 700mg/kg (700mg/kg) BEHAVIORAL: ANALGESIA European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 21, Pg. 277, 1986.
man TDLo oral 17500ug/kg/3W (17.5mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED
Annals of Internal Medicine. Vol. 41, Pg. 1075, 1954.
man TDLo oral 2426mg/kg/24H (2426mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Annals of Emergency Medicine. Vol. 20, Pg. 204, 1991.
man TDLo unreported 200mg/kg/5W-I (200mg/kg) VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED

KIDNEY, URETER, AND BLADDER: HEMATURIA
British Medical Journal. Vol. 282, Pg. 950, 1981.
mouse LD50 intramuscular 430mg/kg (430mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Oyo Yakuri. Pharmacometrics. Vol. 13, Pg. 97, 1977.
mouse LD50 intraperitoneal 128mg/kg (128mg/kg)   Pharmaceutical Chemistry Journal Vol. 19, Pg. 33, 1985.
mouse LD50 intravenous 90mg/kg (90mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 36, 1969.
mouse LD50 oral 238mg/kg (238mg/kg)   Pharmacological Research Communications. Vol. 18, Pg. 241, 1986.
mouse LD50 subcutaneous 230mg/kg (230mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 7, Pg. 1022, 1955.
mouse LD50 unreported 128mg/kg (128mg/kg)   Farmatsevtichnii Zhurnal Vol. (5), Pg. 26, 1983.
rabbit LD50 intravenous 146mg/kg (146mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 129, 1960.
rabbit LD50 oral 781mg/kg (781mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Oyo Yakuri. Pharmacometrics. Vol. 20, Pg. 265, 1980.
rat LD50 intramuscular 220mg/kg (220mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 665, 1960.
rat LD50 intraperitoneal 142mg/kg (142mg/kg)   Farmaco, Edizione Scientifica. Vol. 14, Pg. 347, 1959.
rat LD50 intravenous 100mg/kg (100mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 665, 1960.
rat LD50 oral 245mg/kg (245mg/kg) BEHAVIORAL: ANALGESIA Archives Internationales de Pharmacodynamie et de Therapie. Vol. 123, Pg. 48, 1959.
rat LD50 subcutaneous 230mg/kg (230mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1285, 1972.
women TDLo oral 168mg/kg/4W-I (168mg/kg) VASCULAR: OTHER CHANGES

KIDNEY, URETER, AND BLADDER: CHANGES PRIMARILY IN GLOMERULI
Archives of Internal Medicine. Vol. 145, Pg. 685, 1985.
women TDLo unreported 40mg/kg/4D-I (40mg/kg) BLOOD: LEUKOPENIA

BLOOD: AGRANULOCYTOSIS
Problemy Gematologii i Perelivaniia Krovi. Problems of Hematology and Blood Transfusion. Vol. 4(5), Pg. 48, 1959.

Phenylbutazone Consensus Reports

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 316.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Inadequate Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 13 (1977),p. 183.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . EPA Genetic Toxicology Program. Reported in EPA TSCA Inventory.

Phenylbutazone Safety Profile

Hazard Codes: HarmfulXn,ToxicT
Risk Statements: 36/37/38-20/21/22-42/43-45
R36/37/38:Irritating to eyes, respiratory system and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed. 
R42/43:May cause sensitization by inhalation and skin contact. 
R45:May cause cancer.
Safety Statements: 36/37/39-26-45-22-53
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S22:Do not breathe dust. 
S53:Avoid exposure - obtain special instructions before use.
RIDADR: 3249
RTECS: UQ8225000
HazardClass: 6.1(b)
PackingGroup: III
Hazardous Substances Data: 50-33-9(Hazardous Substances Data)
Suspected human carcinogen producing leukemia. A human poison by parenteral route. An experimental poison by ingestion, intraperitoneal, subcutaneous, intravenous, and intramuscular routes. Human systemic effects by ingestion and possibly other routes: fever, blood pressure increase, other unspecified vascular effects, damage to kidney tubules and glomeruli, decreased urine volume, blood in the urine, reduction in the number of white blood cells, and agranulocytosis. Experimental teratogenic and reproductive effects. Human mutation data reported. An eye irritant. An anti-inflammatory agent. When heated to decomposition it emits toxic fumes of NOx.

Phenylbutazone Specification

  4-Butyl-1,2-diphenyl-3,5-dioxopyrazolidine , its cas register number is 50-33-9. It also can be called 'Esteve' ; 1,2-Diphenyl-3,5-dioxo-4-butylpyrazolidine ; 3,5-Dioxe-4 buty-1, diphenyl-pyrazolidine ; 5-24-05-00400 (Beilstein Handbook Reference) ; Alindor ; Alkabutazona ; Alqoverin ; Anerval ; Anpuzone ; Antadol ; Anuspiramin ; Arthrizon ; Artrizin ; 
 Artrizone ; Artropan ; Azobutyl ; Azolid ; Benzone ; Betazed ; Bizolin ; Bizolin 200 ; Bunetzone ; Busone ; Buta phen ;
 Butacompren ; Butacote ; Butadion ; Butadiona ; Butadione ; Butadionum ; Butagesic ; Butalgina ; Butalidon ; Butaluy ;
 Butaphen ; Butapirazol ; Butapirazole ; Butapyrazole ; Butarecbon ; Butartril ; Butartrina ; Butazina ; Butazolidin ; 
 Butazolidine ; Butazona ; Bute ; Butidiona ; Butiwas-simple ; Butone ; Butoz ; Butylpyrin ; Buvetzone ; Buzon ;
 Chembutazone ; Digibutina ; Diossidone ; Diozol ; Diphebuzol ; Diphenylbutazone ; Ecobutazone ; Elmedal ; Equi bute ;
 Equipalazone ; Eributazone ; Exrheudon N ; Febuzina ; Fenartil ; Fenibutal ; Fenibutasan ; Fenibutazona ; Fenibutol ;
 Fenilbutazona ; Fenilbutazone ; Fenilbutina ; Fenilbutine ; Fenilidina ; Fenotone ; Fenylbutazon ; Intalbut ; Intrabutazone ;
 Mephabutazon ; Phebuzin ; Phebuzine ; Phen-Buta-Vet ; Phenbutazol ; Phenopyrine ; Phenyl-mobuzon ; Pyrazolidin ;
 Scanbutazone ; Schemergen ; UNII-GN5P7K3T8S . 4-Butyl-1,2-diphenyl-3,5-dioxopyrazolidine (CAS NO.50-33-9) is a off-whtie Solid.

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