Basic information
- CAS
129-20-4- Standard SMILES
CCCCC1C(=O)N(c2ccccc2)N(c2ccc(O)cc2)C1=O- InChIKey
HFHZKZSRXITVMK-UHFFFAOYSA-N- Molecular formula
- C19H20N2O3
- Average molar mass
- 324.4 g/mol
- Monoisotopic mass
- 324.1473925
Overview
Oxyphenbutazone is 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 Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following association with blood dyscrasis and Stevens-Johnson syndrome. It has a role as an antimicrobial agent, a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, an antineoplastic agent, a gout suppressant, a drug metabolite and a xenobiotic metabolite. It is a member of phenols and a member of pyrazolidines. It is functionally related to a phenylbutazone.
Names & identifiers
- Preferred name
- Oxazolidin
- IUPAC
- 4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
- English name
- OXYPHENYL BUTAZONE
- Molecular formula
- C19H20N2O3
- Molecular weight
- 324.37
Names & synonyms
oxyphenbutazone129-20-4OxyphenylbutazoneTandearilFlogitoloFlogorilFrabelOxalidNeo-FarmadolCrovarilOxazolidinVisubutina
Show more names
bm1BM 1Flogalg27202IridilMysiteNeofen
OxifenylbutazonOxiphenbutazoneButapironeCalifornitTandacoteFlamarilOxyphenobutazonep-Oxyphenylbutazone
Database identifiers
- CAS
129-20-4、7081-38-1- PubChem CID
- 4641
- DTXSID
DTXSID1045291- ChEMBL
CHEMBL1228、CHEMBL3989676- ChEBI
CHEBI:76258- UNII
- A7D84513GV
- EC Number
- 204-936-2
- Nikkaji
- J10.648H
Properties
Computed structural properties
- XLogP
- 2.7
- Topological polar surface area
- 60.9 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 5
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 454
Experimental & physicochemical properties
LogP3.04
OdorODORLESS
Color/FormWHITE TO YELLOWISH WHITE, CRYSTALLINE POWDER
Solubility
ANHYDROUS CRYSTALS FROM ETHER & PETROLEUM ETHER WITH MP 124-125 °C; ACIDIC REACTION; MP 96 °C; FORMS WATER-SOL SODIUM SALT; SOL IN ETHANOL, METHANOL, CHLOROFORM, BENZENE, ETHER /MONOHYDRATE/
VERY SLIGHTLY SOL IN WATER; FREELY SOL IN ACETONE
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Pharmaceuticals
Collision Cross Section
163.33 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
177.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
184.74 Ų [M-H]-
Physicochemical properties
- Melting point
- 109 · 109-111°C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P273, P301+P317, P330, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Other Safety InformationIMAP assessments - 3,5-Pyrazolidinedione, 4-butyl-1-(4-hydroxyphenyl)-2-phenyl-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Interactions
SOME TRICYCLIC COMPD HAVE BEEN SHOWN TO DELAY OXYPHENYLBUTAZONE ABSORPTION IN RAT BY INCR GASTRIC EMPTYING TIME.
...OXYPHENBUTAZONE MAY PROLONG PROTHROMBIN TIME IN PT RECEIVING COUMARIN ANTICOAGULANTS CONCOMITANTLY & MAY INCR HYPOGLYCEMIC EFFECT OF INSULIN & ORAL HYPOGLYCEMIC AGENTS.
WHEN OXYPHENBUTAZONE & METHANDROSTENOLONE ARE ADMIN CONCURRENTLY IN HUMANS, SERUM OXYPHENBUTAZONE LEVELS MAY BE ELEVATED. PT TREATED WITH THESE CONCURRENTLY SHOULD BE MONITORED FOR SIGNS OF OXYPHENBUTAZONE-INDUCED ADVERSE EFFECTS.
OXYPHENBUTAZONE ABSORPTION...IS DECR BY DESIPRAMINE.
For more Interactions (Complete) data for OXYPHENBUTAZONE (6 total), please visit the HSDB record page.
Human Toxicity Excerpts
NAUSEA, VOMITING, EPIGASTRIC DISCOMFORT, & SKIN RASHES ARE MOST FREQUENTLY REPORTED UNTOWARD EFFECTS. DIARRHEA, VERTIGO, INSOMNIA, EUPHORIA, NERVOUSNESS, HEMATURIA...& BLURRED VISION HAVE ALSO BEEN OBSERVED. ...WATER & ELECTROLYTE RETENTION & EDEMA FORMATION OCCUR. /PHENYLBUTAZONE/
Chemistry & industry
Pharmacology
ATC Code
S - Sensory organs
M - Musculo-skeletal system
M - Musculo-skeletal system
QM - Musculo-skeletal system
QS - Sensory organs
QM - Musculo-skeletal system
Mechanism of Action
...HAS PROMINENT ANTI-INFLAMMATORY EFFECTS IN ANIMALS, & COMPARABLE EFFECTS... IN PT WITH RHEUMATOID ARTHRITIS & RELATED DISORDERS. ...INHIBITS BIOSYNTHESIS OF PROSTAGLANDINS, UNCOUPLES OXIDATIVE PHOSPHORYLATION, & INHIBITS ATP-DEPENDENT BIOSYNTHESIS OF MUCOPOLYSACCHARIDE SULFATES IN CARTILAGE. /PHENYLBUTAZONE/
Biological Half-LifeIN MAN, OXYPHENBUTAZONE HAS BIOLOGICAL HALF-LIFE OF ABOUT 2 DAYS.
Metabolism/MetabolitesOXIDN OF PHENYLBUTAZONE DURING CHRONIC DOSING BY MEASURING URINARY EXCRETION OF 3 METABOLITES, OXYPHENBUTAZONE GAMMA-HYDROXYPHENBUTAZONE & P,GAMMA-HYDROXYPHENBUTAZONE DURING INFUSION OF HYDROCORTISONE SODIUM SUCCINATE IS REPORTED.
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Absorption, Distribution and Excretion
...OXYPHENBUTAZONE IS EXTENSIVELY BOUND TO PLASMA PROTEINS & HAS PLASMA HALF-TIME OF SEVERAL DAYS. ...ONLY SLOWLY EXCRETED IN URINE, SINCE BINDING TO PLASMA PROTEIN LIMITS...GLOMERULAR FILTRATION, &...RELATIVELY HIGH PKA, WHICH FAVORS PASSIVE REABSORPTION IN DISTAL TUBULE.
Uses & manufacturing
Related reactions
5 records
Compound notes
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