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Substance Name: Oxyphenbutazone [INN]
RN: 129-20-4
UNII: A7D84513GV
InChIKey: HFHZKZSRXITVMK-UHFFFAOYSA-N

Note

  • A non-steroidal anti-inflammatory drug. Oxyphenbutazone eyedrops have been used abroad in the management of postoperative ocular inflammation, superficial eye injuries, and episcleritis. (From AMA, Drug Evaluations Annual, 1994, p2000) It had been used by mouth in rheumatic disorders such as ankylosing spondylitis, osteoarthritis, and rheumatoid arthritis but such use is no longer considered justified owing to the risk of severe hematological adverse effects. (From Martindale, The Extra Pharmacopoeia, 30th ed, p27)

Molecular Formula

  • C19-H20-N2-O3

Molecular Weight

  • 324.378
 

Classification Codes

Classification Codes

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

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3
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Names and Synonyms

Name of Substance

  • Oxyphenbutazone
  • Oxyphenbutazone [INN]

MeSH Heading

  • Oxyphenbutazone

Synonyms

  • 1-(p-Hydroxyphenyl)-2-phenyl-4-butyl-3,5-pyrazolidinedione
  • 1-p-Hydroxyphenyl-2-phenyl-3,5-dioxo-4-N-butylpyrazolidine
  • 1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-butylpyrazolidine
  • 1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-n-butylpyrazolidine
  • 3,5-Dioxo-1-phenyl-2-(p-hydroxyphenyl)-4-N-butylpyrazolidene
  • 3,5-Pyrazolidinedione, 4-butyl-1-(4-hydroxyphenyl)-2-phenyl
  • 3,5-Pyrazolidinedione, 4-butyl-1-(p-hydroxyphenyl)-2-phenyl-
  • 4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione
  • 4-Butyl-1-(p-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione
  • 4-Butyl-2-(4-hydroxyphenyl)-1-phenyl-3,5-dioxopyrazolidine
  • 4-Butyl-2-(p-hydroxyphenyl)-1-phenyl-3,5-pyrazolidinedione
  • 5-24-05-00404 (Beilstein Handbook Reference)
  • AI3-26792
  • Aradinum
  • Artroflog
  • BM 1
  • BRN 0307474
  • Butaflogin
  • Butanora
  • Butanova
  • Butapirone
  • Butazonic
  • Butilene
  • Californit
  • CCRIS 6717
  • Cinophen-N
  • Crovaril
  • Deflogin
  • EINECS 204-936-2
  • Etrozolidina
  • Flamaril
  • Flanaril
  • Flegmostam
  • Flogal
  • Floghene
  • Flogistin
  • Flogitolo
  • Flogodin
  • Flogoril
  • Flogostop
  • Flopirina
  • Frabel
  • G 27202
  • Genal
  • HSDB 3144
  • Hydroxyphenylbutazon
  • Idrobutazina
  • Infamil
  • Infammil
  • Ipabutona
  • Iridil
  • Isobutazina
  • Isobutil
  • Metabolite I
  • Mysite
  • Neo-farmadol
  • Neofen
  • NSC 526053
  • Offitril
  • Optimal
  • Ossifenbutazone
  • Ossifenbutazone [DCIT]
  • Oxalid
  • Oxazolidin
  • Oxazolidin-geigy
  • Oxazolioin
  • Oxi-fenibutol
  • Oxibutol
  • Oxifenbutazona
  • Oxifenbutazona [INN-Spanish]
  • Oxifenylbutazon
  • Oxiphenbutazone
  • Oxiphenbutazonum
  • Oxybuton
  • Oxyphenbutazone
  • Oxyphenbutazone anhydrous
  • Oxyphenbutazonum
  • Oxyphenbutazonum [INN-Latin]
  • Oxyphenobutazone
  • Oxyphentamin
  • Oxyphenylbutazone
  • p-Hydroxyphenylbutazone
  • p-Oxyphenylbutazone
  • Pirabutina
  • Piraflogin
  • Poliflogil
  • Portoril
  • Rapostan
  • Remazin
  • Reumox
  • Reunabutal
  • Rumapax
  • Tandacote
  • Tandalgesic
  • Tandearil
  • Tanderil
  • Telidac
  • Telidal
  • Tendearil
  • UNII-A7D84513GV
  • USAF GE-14
  • Valioil
  • Visubutina

Systematic Names

  • 3,5-Pyrazolidinedione, 4-butyl-1-(4-hydroxyphenyl)-2-phenyl- (9CI)
  • 3,5-Pyrazolidinedione, 4-butyl-1-(p-hydroxyphenyl)-2-phenyl-
  • 3,5-Pyrazolidinedione, 4-butyl-1-(p-hydroxyphenyl)-2-phenyl- (VAN) (8CI)
  • Oxyphenbutazone

Superlist Name

  • Oxyphenbutazone

Registry Numbers

CAS Registry Number

  • 129-20-4

FDA UNII

  • A7D84513GV

System Generated Number

  • 0000129204

Structure Descriptors

InChI

1S/C19H20N2O3/c1-2-3-9-17-18(23)20(14-7-5-4-6-8-14)21(19(17)24)15-10-12-16(22)13-11-15/h4-8,10-13,17,22H,2-3,9H2,1H3

InChIKey

HFHZKZSRXITVMK-UHFFFAOYSA-N

Smiles

CCCCC1C(=O)N(N(C1=O)c2ccc(cc2)O)c3ccccc3

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 420mg/kg/4W-I (420mg/kg) LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

BLOOD: AGRANULOCYTOSIS

BLOOD: THROMBOCYTOPENIA
British Medical Journal. Vol. 2, Pg. 1517, 1962.
dog LD50 intravenous 178mg/kg (178mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Archives Internationales de Pharmacodynamie et de Therapie. Vol. 149, Pg. 571, 1964.
guinea pig LD50 oral 1165mg/kg (1165mg/kg)   Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 11, Pg. 220, 1974.
hamster LD50 oral 1180mg/kg (1180mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
man TDLo oral 27mg/kg/14D (27mg/kg) BLOOD: HEMORRHAGE

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

GASTROINTESTINAL: NAUSEA OR VOMITING
Laekartidningen. Medical News. Vol. 63, Pg. 53, 1966.
mouse LD50 intraperitoneal 100mg/kg (100mg/kg)   National Technical Information Service. Vol. AD414-344,
mouse LD50 intravenous 52mg/kg (52mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 129, 1960.
mouse LD50 oral 330mg/kg (330mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 63, Pg. 43, 1967.
rabbit LD50 intravenous 104mg/kg (104mg/kg) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS
Annals of the New York Academy of Sciences. Vol. 86, Pg. 263, 1960.
rat LD50 intraperitoneal 145mg/kg (145mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 63, Pg. 43, 1967.
rat LD50 intravenous 68mg/kg (68mg/kg)   Medicina Experimentalis. Vol. 6, Pg. 88, 1962.
rat LD50 oral 329mg/kg (329mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 63, Pg. 43, 1967.
women TDLo oral 24mg/kg/4D (24mg/kg) ENDOCRINE: OTHER CHANGES

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS
JAMA, Journal of the American Medical Association. Vol. 238, Pg. 1399, 1977.
women TDLo oral 50mg/kg/7D (50mg/kg)   Laekartidningen. Medical News. Vol. 63, Pg. 53, 1966.
women TDLo oral 50mg/kg/7D (50mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Laekartidningen. Medical News. Vol. 63, Pg. 53, 1966.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 96 deg C   EXP
log P (octanol-water) 2.72 (none)   EXP
Water Solubility 60 mg/L 30 EXP
Vapor Pressure 2.70E-12 mm Hg 25 EST
Henry's Law Constant 6.83E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.81E-11 cm3/molecule-sec 25 EST

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