Oxyphenbutazone

Identification

Summary

Oxyphenbutazone is a nonsteroidal anti-inflammatory drug (NSAID) no longer commonly used for the symptomatic relief of musculoskeletal pain.

Generic Name
Oxyphenbutazone
DrugBank Accession Number
DB03585
Background

Oxyphenbutazone was withdrawn from the Canadian market in March 1985 due to concerns regarding bone marrow suppression.

Type
Small Molecule
Groups
Approved, Withdrawn
Structure
Thumb
Weight
Average: 324.3737
Monoisotopic: 324.147392516
Chemical Formula
C19H20N2O3
Synonyms
  • Oxifenbutazona
  • Oxiphenbutazone
  • Oxyphenbutazone
  • Oxyphenbutazonum
External IDs
  • USAF Ge-14

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGroup IIE secretory phospholipase A2Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirOxyphenbutazone may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Oxyphenbutazone is combined with Abciximab.
AcebutololOxyphenbutazone may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Oxyphenbutazone is combined with Aceclofenac.
AcemetacinThe risk or severity of adverse effects can be increased when Oxyphenbutazone is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Oxyphenbutazone is combined with Acenocoumarol.
AcetaminophenThe risk or severity of adverse effects can be increased when Acetaminophen is combined with Oxyphenbutazone.
AcetohexamideThe protein binding of Acetohexamide can be decreased when combined with Oxyphenbutazone.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Oxyphenbutazone.
AclidiniumOxyphenbutazone may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Interactions
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Food Interactions
  • Take with food. Food reduces irritation.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Oxyphenbutazone monohydrateH806S4B3NS7081-38-1CNDQSXOVEQXJOE-UHFFFAOYSA-N
International/Other Brands
Oxyphenbutazone / Reozon
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Oxybutazone Tab 100mgTablet100 mgOralIcn Pharmaceuticals1981-12-312005-04-26Canada flag
Oxyphenbutazone 100mg TabletsTablet100 mg / tabOralLaboratoires Confab IncNot applicableNot applicableCanada flag

Categories

ATC Codes
M01AA03 — OxyphenbutazoneM02AA04 — OxyphenbutazoneS01BC02 — Oxyphenbutazone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that a unsubstituted at the 2-position.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
1-hydroxy-2-unsubstituted benzenoids
Direct Parent
1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Pyrazolidinones / Benzene and substituted derivatives / 1,3-dicarbonyl compounds / Carboxylic acid hydrazides / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
1,3-dicarbonyl compound / 1-hydroxy-2-unsubstituted benzenoid / Aromatic heteromonocyclic compound / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid hydrazide / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
phenols, pyrazolidines (CHEBI:76258)
Affected organisms
Not Available

Chemical Identifiers

UNII
A7D84513GV
CAS number
129-20-4
InChI Key
HFHZKZSRXITVMK-UHFFFAOYSA-N
InChI
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
IUPAC Name
4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione
SMILES
CCCCC1C(=O)N(N(C1=O)C1=CC=C(O)C=C1)C1=CC=CC=C1

References

General References
Not Available
KEGG Compound
C19494
PubChem Compound
4641
PubChem Substance
46507285
ChemSpider
4480
BindingDB
200298
RxNav
7816
ChEBI
76258
ChEMBL
CHEMBL1228
PharmGKB
PA450750
PDBe Ligand
OPB
Wikipedia
Oxyphenbutazone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral100 mg
TabletOral100 mg / tab
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)96 °CPhysProp
water solubility60 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.72HANSCH,C ET AL. (1995)
logS-3.73ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.256 mg/mLALOGPS
logP2.79ALOGPS
logP3.83ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.87ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.85 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity90.74 m3·mol-1ChemAxon
Polarizability35.14 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9238
Caco-2 permeable+0.5303
P-glycoprotein substrateNon-substrate0.7216
P-glycoprotein inhibitor INon-inhibitor0.7803
P-glycoprotein inhibitor IIInhibitor0.6587
Renal organic cation transporterNon-inhibitor0.8981
CYP450 2C9 substrateNon-substrate0.6167
CYP450 2D6 substrateNon-substrate0.8844
CYP450 3A4 substrateNon-substrate0.5538
CYP450 1A2 substrateInhibitor0.7253
CYP450 2C9 inhibitorInhibitor0.5
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9035
CYP450 3A4 inhibitorInhibitor0.796
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6021
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.7686
BiodegradationNot ready biodegradable0.9847
Rat acute toxicity2.9626 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9507
hERG inhibition (predictor II)Non-inhibitor0.924
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9601000000-0e93b2309b6f4ff21792
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-3920000000-8a5be556648d9ff3213b

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phospholipase a2 activity
Specific Function
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids.
Gene Name
PLA2G2E
Uniprot ID
Q9NZK7
Uniprot Name
Group IIE secretory phospholipase A2
Molecular Weight
15988.525 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Bertucci C, Wainer IW: Improved chromatographic performance of a modified human albumin based stationary phase. Chirality. 1997;9(4):335-40. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Apiwattanakul N, Sekine T, Chairoungdua A, Kanai Y, Nakajima N, Sophasan S, Endou H: Transport properties of nonsteroidal anti-inflammatory drugs by organic anion transporter 1 expressed in Xenopus laevis oocytes. Mol Pharmacol. 1999 May;55(5):847-54. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 24, 2021 16:00