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Substance Name: Phenylbutazone [USP:INN:BAN:JAN]
RN: 50-33-9
UNII: GN5P7K3T8S
InChIKey: VYMDGNCVAMGZFE-UHFFFAOYSA-N

Note

  • A butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. It has been used in ANKYLOSING SPONDYLITIS; RHEUMATOID ARTHRITIS; and REACTIVE ARTHRITIS.

Molecular Formula

  • C19-H20-N2-O2

Molecular Weight

  • 308.379
 

Classification Codes

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-Inflammatory Agents
  • Anti-Inflammatory Agents, Non-Steroidal
  • Antirheumatic
  • Antirheumatic Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents
  • Skin / Eye Irritant
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3

Names and Synonyms

Name of Substance

  • Phenylbutazone
  • Phenylbutazone [USP:INN:BAN:JAN]

MeSH Heading

  • Phenylbutazone

Synonyms

  • 1,2-Diphenyl-3,5-dioxo-4-butylpyrazolidine
  • 1,2-Diphenyl-4-butyl-3,5-dioxopyrazolidine
  • 1,2-Diphenyl-4-butyl-3,5-pyrazolidinedione
  • 3,5-Dioxe-4 buty-1, diphenyl-pyrazolidine
  • 3,5-Dioxo-1,2-diphenyl-4-n-butyl-pyrazolidin
  • 3,5-Dioxo-1,2-diphenyl-4-n-butylpyrazolidine
  • 3,5-Pyrazolidinedione, 4-butyl-1,2-diphenyl-
  • 4-Butyl-1,2-diphenyl-3,5-dioxopyrazolidine
  • 4-Butyl-1,2-diphenyl-3,5-pyrazolidinedione
  • 4-n-Butyl-1,2-diphenyl-3,5-pyrazolidinedione
  • 5-24-05-00400 (Beilstein Handbook Reference)
  • A 7514
  • Alindor
  • Alkabutazona
  • Alqoverin
  • Anerval
  • Anpuzone
  • Antadol
  • Anuspiramin
  • Arthrizon
  • Artrizin
  • Artrizone
  • Artropan
  • Azobutyl
  • Azolid
  • B.t.z.
  • Benzone
  • Betazed
  • Bizolin
  • Bizolin 200
  • BRN 0290080
  • 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
  • CCRIS 2374
  • Chembutazone
  • DA-192
  • Digibutina
  • Diossidone
  • Diozol
  • Diphebuzol
  • Diphenylbutazone
  • Ecobutazone
  • EINECS 200-029-0
  • Elmedal
  • Equi bute
  • Equipalazone
  • Eributazone
  • Exrheudon N
  • Febuzina
  • Fenartil
  • Fenibutal
  • Fenibutasan
  • Fenibutazona
  • Fenibutol
  • Fenilbutazon
  • Fenilbutazona
  • Fenilbutazona [INN-Spanish]
  • Fenilbutazone
  • Fenilbutazone [DCIT]
  • Fenilbutina
  • Fenilbutine
  • Fenilidina
  • Fenotone
  • Fenylbutazon
  • Flexazone
  • G 13,871
  • G 13871
  • HSDB 3159
  • Ia-BuT
  • Intalbut
  • Intrabutazone
  • Intrazone
  • Ipsoflame
  • Kadol
  • Lingel
  • Malgesic
  • Mephabutazon
  • Mephabutazone
  • Merizone
  • Nadazone
  • Nadozone
  • NCI-C56531
  • Neo-zoline
  • Novophenyl
  • NSC 25134
  • PBZ
  • Phebuzin
  • Phebuzine
  • Phen-Buta-Vet
  • Phenbutazol
  • Phenopyrine
  • Phenyl-mobuzon
  • Phenylbutaz
  • Phenylbutazon
  • Phenylbutazon [German]
  • Phenylbutazone
  • Phenylbutazonum
  • Phenylbutazonum [INN-Latin]
  • Phenyzone
  • Pirarreumol B
  • Praecirheumin
  • Pyrabutol
  • Pyrazolidin
  • Rectofasa
  • Reudo
  • Reudox
  • Reumasyl
  • Reumazin
  • Reumazol
  • Reumune
  • Reumuzol
  • Reupolar
  • Robizon-V
  • Robizone
  • Robizone-V
  • Rubatone
  • Scanbutazone
  • Schemergen
  • UNII-GN5P7K3T8S

Systematic Names

  • 3,5-Pyrazolidinedione, 4-butyl-1,2-diphenyl-
  • Phenylbutazone

Superlist Name

  • Phenylbutazone

Registry Numbers

CAS Registry Number

  • 50-33-9

FDA UNII

  • GN5P7K3T8S

Other Registry Number

  • 4297-92-1

System Generated Number

  • 0000050339

Structure Descriptors

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

Smiles

CCCCC1C(=O)N(N(C1=O)c2ccccc2)c3ccccc3

Toxicity

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)   Annals of Emergency Medicine. Vol. 20, Pg. 204, 1991.
man TDLo oral 2426mg/kg/24H (2426mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Annals of Emergency Medicine. Vol. 20, Pg. 204, 1991.
man TDLo unreported 200mg/kg/5W-I (200mg/kg) KIDNEY, URETER, AND BLADDER: HEMATURIA

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED

VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION
British Medical Journal. Vol. 282, Pg. 950, 1981.
mouse LD50 intramuscular 430mg/kg (430mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
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: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 129, 1960.
rabbit LD50 oral 781mg/kg (781mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
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: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
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.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 105 deg C   EXP
pKa Dissociation Constant 4.5 (none)   EXP
log P (octanol-water) 3.16 (none)   EXP
Water Solubility 47.5 mg/L 30 EXP
Vapor Pressure 2.97E-10 mm Hg 25 EST
Henry's Law Constant 6.56E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.29E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.