phenyl butazone
Notes:
a butyl-diphenyl-pyrazolidinedione that has anti-inflammatory, antipyretic, and analgesic activities. it has been used in ankylosing spondylitis; rheumatoid arthritis; and reactive arthritis.
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4-butyl-1,2-diphenylpyrazolidine-3,5-dione (Click)
CAS Number: 50-33-9 4297-92-1
ECHA EC Number:200-029-0
FDA UNII:GN5P7K3T8S
Beilstein Number:0290080
MDL:MFCD00005500
XlogP3:3.20 (est)
Molecular Weight:308.38080000
Formula:C19 H20 N2 O2
BioActivity Summary:listing
NMR Predictor:Predict
Category:pharmaceuticals / chemical synthisis
 
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Physical Properties:
Appearance:white crystalline powder (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed:No
Melting Point: 105.00 °C. @ 760.00 mm Hg
Boiling Point: 424.89 °C. @ 760.00 mm Hg (est)
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Organoleptic Properties:
  
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Cosmetic Information:
None found
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Suppliers:
Santa Cruz Biotechnology
Phenylbutazone ≥99%
For experimental / research use only.
Sigma-Aldrich: Sigma
Phenylbutazone
For experimental / research use only.
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Safety Information:
Oral/Parenteral Toxicity:
  intravenous-cat LD50  100 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 36, 1969.

intravenous-dog LD50  121 mg/kg
BEHAVIORAL: ANALGESIA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 149, Pg. 571, 1964.

oral-dog LD50  332 mg/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.

oral-guinea pig LD50  250 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 1207, 1969.

oral-hamster LD50  1260 mg/kg
Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.

intraperitoneal-mammal (species unspecified) LD50  300 mg/kg
BEHAVIORAL: ANALGESIA
European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 21, Pg. 277, 1986.

oral-mammal (species unspecified) LD50  700 mg/kg
BEHAVIORAL: ANALGESIA
European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 21, Pg. 277, 1986.

oral-man TDLo  17500 ug/kg/3W
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.

oral-man TDLo  2426 mg/kg/24H
LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Annals of Emergency Medicine. Vol. 20, Pg. 204, 1991.

unreported-man TDLo  200 mg/kg/5W-I
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.

intramuscular-mouse LD50  430 mg/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.

intraperitoneal-mouse LD50  128 mg/kg
Pharmaceutical Chemistry Journal Vol. 19, Pg. 33, 1985.

intravenous-mouse LD50  90 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 36, 1969.

oral-mouse LD50  238 mg/kg
Pharmacological Research Communications. Vol. 18, Pg. 241, 1986.

unreported-mouse LD50  128 mg/kg
Farmatsevtichnii Zhurnal Vol. (5), Pg. 26, 1983.

intravenous-rabbit LD50  146 mg/kg
BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 129, 1960.

oral-rabbit LD50  781 mg/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.

intramuscular-rat LD50  220 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 665, 1960.

intraperitoneal-rat LD50  142 mg/kg
Farmaco, Edizione Scientifica. Vol. 14, Pg. 347, 1959.

intravenous-rat LD50  100 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 665, 1960.

oral-rat LD50  245 mg/kg
BEHAVIORAL: ANALGESIA
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 123, Pg. 48, 1959.

Dermal Toxicity:
  subcutaneous-mouse LD50 230 mg/kg
Journal of Pharmacy and Pharmacology. Vol. 7, Pg. 1022, 1955.

subcutaneous-rat LD50 230 mg/kg
BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 1285, 1972.

Inhalation Toxicity:
  Not determined
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Safety in Use Information:
Category:pharmaceuticals / chemical synthisis
Recommendation for phenyl butazone usage levels up to:
 not for fragrance use.
Recommendation for phenyl butazone flavor usage levels up to:
 not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
Joint Statement of EFSA and EMA on the presence of residues of phenylbutazone in horse meat
page or pdf
EPI System:View
Chemicalize.org:Calculate predicted properties
Daily Med:search
NLM Hazardous Substances Data Bank:Search
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Carcinogenic Potency Database:Search
EPA GENetic TOXicology:Search
Env. Mutagen Info. Center:Search
National Toxicology Program:Search
EPA Substance Registry Services (TSCA):50-33-9
EPA ACToR:Toxicology Data
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
 4-butyl-1,2-diphenylpyrazolidine-3,5-dione
DTP/NCI:25134
Chemidplus:0000050339
EPA/NOAA CAMEO:hazardous materials
RTECS:UQ8225000 for cas# 50-33-9
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References:
 4-butyl-1,2-diphenylpyrazolidine-3,5-dione
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:50-33-9
Pubchem (cid):4781
Pubchem (sid):134971182
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Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
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Export Tariff Code:2933.19.4000
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Wikipedia: View
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Formulations/Preparations:
•phenylbutazone tablets containing 100 mg and 1000 mg of active ingredient are available for oral administration to dogs and horses, respectively, for treatment of inflammation associated with the musculoskeletal system. phenylbutazone solution for intravenous injection contains 200 mgml of active ingredient and is indicated for the relief of inflammation associated with the musculoskeletal system of the horse. •grade: national formulary •oral capsules, 100 mg; phenylbutazone capsules, barr, cmc, interstate, major, rugby; tablets film-coated, 100 mg; phenylbutazone tablets, barr, cmc, interstate, major, rugby, united research.
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Potential Blenders and core components note
None Found
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Potential Uses:
None Found
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Natural Occurrence in: note
 not found in nature
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Synonyms:
4-butyl-1,2 -diphenyl-3,5-dioxo pyrazolidine
4-butyl-1,2-diphenyl-1,2-diazolidine-3,5-dione
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
4-butyl-1,2-diphenyl-pyrazolidine-3,5-dione
4-butyl-1,2-diphenylpyrazolidine-3,5-dione
3,5-dioxo-1,2-diphenyl-4-N-butylpyrazolidine
3,5-dioxo-4-butyl-1-diphenyl-pyrazolidine
1,2-diphenyl-2,3-dioxo-4-N-butylpyrazoline
1,2-diphenyl-3,5-dioxo-4-butylpyrazolidine
1,2-diphenyl-3,5-dioxo-4-N-butylpyrazoline
1,2-diphenyl-4-butyl-3,5-dioxopyrazolidine
1,2-diphenyl-4-butyl-3,5-pyrazolidinedione
 mepha-butazon
 phenbutazone
 phenylbutazone
 phenylbutazonum
 phenyzene
 pyrasanone
 pyrazinobutazone
3,5-pyrazolidinedione, 4-butyl-1,2-diphenyl-
 Ranoroc
 shigrodin
 tencodyne
 tetnor
 tevcodyne
 therazone
 ticinil
 todalgil
 zolidinum
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Articles:
Info:Phenylbutazone
PubMed:Veterinary drug residues in domestic and imported foods of animal origin in the Republic of Korea.
PubMed:Investigation into sources of contamination of cattle with phenylbutazone.
PubMed:Pharmacokinetics, pharmacodynamics, metabolism, toxicology and residues of phenylbutazone in humans and horses.
PubMed:Bute residues of low concern for consumers, say EFSA and EMA.
PubMed:EC seeks advice on risks from phenylbutazone in horsemeat.
PubMed:"Bute" in horse meat presents very low risk to health, says England's chief medical officer.
PubMed:Development and validation of two multiresidue liquid chromatography tandem mass spectrometry methods based on a versatile extraction procedure for isolating non-steroidal anti-inflammatory drugs from bovine milk and muscle tissue.
PubMed:Food and Chemical Toxicology, 2010, Association of phenylbutazone usage in horses bought for slaughter: a public health risk.
PubMed:Development and validation of a confirmatory method for the determination of 12 non steroidal anti-inflammatory drugs in milk using liquid chromatography-tandem mass spectrometry.
PubMed:Quantification of anthelmintic drug residues in milk and muscle tissues by liquid chromatography coupled to Orbitrap and liquid chromatography coupled to tandem mass spectrometry.
PubMed:Simultaneous determination of 20 pharmacologically active substances in cow's milk, goat's milk, and human breast milk by gas chromatography-mass spectrometry.
PubMed:Surveillance study of novobiocin and phenylbutazone residues in raw bovine milk using liquid chromatography-tandem mass spectrometry.
PubMed:Identification of the human UDP-glucuronosyltransferases involved in the glucuronidation of combretastatin A-4.
PubMed:Association of phenylbutazone usage with horses bought for slaughter: a public health risk.
PubMed:A survey on two years of medication regulation in horse races in Iran.
PubMed:Multicentre, controlled, randomised and blinded field study comparing efficacy of suxibuzone and phenylbutazone in lame horses.
PubMed:Interaction of polyphenolic metabolites with human serum albumin: a circular dichroism study.
PubMed:Determination of ibuprofen, ketoprofen, diclofenac and phenylbutazone in bovine milk by gas chromatography-tandem mass spectrometry.
PubMed:An update on nonsteroidal anti-inflammatory drugs (NSAIDs) in small animals.
PubMed:Extralabel use of nonsteroidal anti-inflammatory drugs in cattle.
PubMed:Confirmatory identification of sixteen non-steroidal anti-inflammatory drug residues in raw milk by liquid chromatography coupled with ion trap mass spectrometry.
PubMed:Surveillance for selected bacterial and toxicologic contaminants in donated carcass meat fed to carnivores.
PubMed:Use of accelerating solvent extraction for detecting non-steroidal anti-inflammatory drugs in horse feces.
PubMed:Left otitis media/interna and right maxillary sinusitis in a Percheron mare.
PubMed:Comparison of the effect of Sporobolus virginicus and Rhodes (Chloris gayana) hay diets on the absorption pattern of phenylbutazone in the camel (Camelus dromedarius).
PubMed:Multi-residue liquid chromatography/tandem mass spectrometry method for the detection of non-steroidal anti-inflammatory drugs in bovine muscle: optimisation of ion trap parameters.
PubMed:Ornithine transcarbamylase deficiency: a urea cycle defect.
PubMed:Preliminary studies of offspring exposure to phenylbutazone and ivermectin during the perinatal period in a Holstein cow-calf model.
PubMed:Pharmacokinetics of phenylbutazone in beef steers.
PubMed:Late diagnosis of ornithine transcarbamylase defect in three related female patients: polymorphic presentations.
PubMed:Determination of non-protein bound phenylbutazone in bovine plasma using ultrafiltration and liquid chromatography with ultraviolet detection.
PubMed:Pharmacokinetics of phenylbutazone in plasma and milk of lactating dairy cows.
PubMed:Ancillary therapy of bovine respiratory disease.
PubMed:Extralabel use of nonsteroidal anti-inflammatory drugs.
PubMed:Effect of evening primrose oil on gastric ulceration and secretion induced by various ulcerogenic and necrotizing agents in rats.
PubMed:Determination of phenylbutazone residues in bovine milk by liquid chromatography with UV detection.
PubMed:[The concentration changes of different phenylbutazone formulations in horse plasma].
PubMed:Interactions of warfarin with drugs and food.
PubMed:Norplant: a welcome new contraceptive.
PubMed:Subdermal contraceptive implants in nurse-midwifery practice.
PubMed:Use of nonsteroidal anti-inflammatory drugs in food animal practice.
PubMed:Contact sensitivity to pyrazinobutazone (Carudol) with positive oral provocation test.
PubMed:Chemicals and drugs as triggers of food-associated disorder.
PubMed:Experimental renal papillary necrosis in the Syrian hamster.
PubMed:Experimental uses of flunixin meglumine and phenylbutazone in food-producing animals.
PubMed:[The pathogenetic significance of prostaglandins in food poisoning and therapy questions].
PubMed:Effects of anti-inflammatory analgesic drugs and muscarinic receptor blocking agents on appetite in the pig.
PubMed:Metabolism, excretion, pharmacokinetics and tissue residues of phenylbutazone in the horse.
PubMed:Risks and indications of phenylbutazone: another look.
PubMed:Lack of effect of non-steroid antiinflammatory drugs on lithium clearance and on delivery of tubular fluid to the loop of Henle in rats.
PubMed:Absorption and pharmacokinetics of phenylbutazone in Welsh Mountain ponies.
PubMed:Genetic and histological aspects of stomach lesions induced by systemic injection of phenylbutazone in the rat.
PubMed:Interactions of analgesics with other drugs.
PubMed:The effect of food on the absorption of phenylbutazone from a commercial 100 mg enteric-coated tablet.
PubMed:Effect of Tomanol on the pharmacokinetics and tissue distribution of penicillin G in dairy cows.
PubMed:Chemically induced leukemia in humans.
PubMed:Therapeutic implications of drug interactions with acetaminophen and aspirin.
PubMed:Evidence for in vitro and in vivo interaction between ochratoxin A and three acidic drugs.
PubMed:Research review. Interactions between environmental chemicals and drug biotransformation in man.
PubMed:[Induction of cleft palate in ball mice: the comparative effect of 5-fluorouracil, phenylbutazone and water and food deprivation (author's transl)].
PubMed:Discriminative stimulus properties of analgesic drugs: narcotic versus non-narcotic analgesics.
PubMed:Further studies on self-administration of antipyretic analgesics and combination of antipyretic analgesics with codeine in rhesus monkeys.
PubMed:Effects of benzoquinolizine homologues on proliferative and exudative inflammation.
PubMed:Indomethacin-induced intestinal lesions in the rat.
PubMed:Pharmacological studies of a new anti-inflammatory drug, 1-phenylsulfonyl-5,5-diphenylhydantoin (PC-796) in experimental animals. II. Toxicological and general pharmacological properties.
PubMed:More about isonicotinic acid hydrazide toxicity.
PubMed:The biopharmaceutical properties of solid dosage forms. I. An evaluation of 23 brands of phenylbutazone tablets.
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Soluble in:
 water, 47.5 mg/L @ 30 °C (exp)
 water, 21.95 mg/L @ 25 °C (est)
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