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Oxyphenbutazone was withdrawn from the Canadian market in March 1985 due to concerns regarding bone marrow suppression.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- Approved, Withdrawn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
Structure for Oxyphenbutazone (DB03585)
- Weight
- Average: 324.3737
Monoisotopic: 324.147392516 - Chemical Formula
- C19H20N2O3
- Synonyms
- Oxifenbutazona
- Oxiphenbutazone
- Oxyphenbutazone
- Oxyphenbutazonum
- External IDs
- USAF Ge-14
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UGroup IIE secretory phospholipase A2 Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Oxyphenbutazone may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The risk or severity of bleeding and hemorrhage can be increased when Oxyphenbutazone is combined with Abciximab. Acebutolol Oxyphenbutazone may decrease the antihypertensive activities of Acebutolol. Aceclofenac The risk or severity of adverse effects can be increased when Oxyphenbutazone is combined with Aceclofenac. Acemetacin The risk or severity of adverse effects can be increased when Oxyphenbutazone is combined with Acemetacin. - Food Interactions
- Take with food. Food reduces irritation.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Oxyphenbutazone monohydrate H806S4B3NS 7081-38-1 CNDQSXOVEQXJOE-UHFFFAOYSA-N - International/Other Brands
- Oxyphenbutazone / Reozon
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Oxybutazone Tab 100mg Tablet 100 mg Oral Icn Pharmaceuticals 1981-12-31 2005-04-26 Canada 
Oxyphenbutazone 100mg Tablets Tablet 100 mg / tab Oral Laboratoires Confab Inc Not applicable Not applicable Canada
Categories
- ATC Codes
- M01AA03 — Oxyphenbutazone
- M01AA — Butylpyrazolidines
- M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
- M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
- M — MUSCULO-SKELETAL SYSTEM
- M02AA — Antiinflammatory preparations, non-steroids for topical use
- M02A — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M02 — TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
- M — MUSCULO-SKELETAL SYSTEM
- Drug Categories
- Agents causing hyperkalemia
- Agents that produce hypertension
- Analgesics
- Analgesics, Non-Narcotic
- Anti-Inflammatory Agents
- Anti-Inflammatory Agents, Non-Steroidal
- Antiinflammatory and Antirheumatic Products
- Antiinflammatory and Antirheumatic Products, Non-Steroids
- Antiinflammatory Preparations, Non-Steroids for Topical Use
- Antirheumatic Agents
- Butylpyrazolidines
- Musculo-Skeletal System
- Nephrotoxic agents
- Non COX-2 selective NSAIDS
- OAT1/SLC22A6 inhibitors
- Ophthalmologicals
- Other Nonsteroidal Anti-inflammatory Agents
- Peripheral Nervous System Agents
- Pyrazoles
- Pyrazolones
- Sensory Organs
- Sensory System Agents
- Topical Products for Joint and Muscular Pain
- 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
- External Links
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 100 mg Tablet Oral 100 mg / tab - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 96 °C PhysProp water solubility 60 mg/L (at 30 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 2.72 HANSCH,C ET AL. (1995) logS -3.73 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.256 mg/mL ALOGPS logP 2.79 ALOGPS logP 3.83 Chemaxon logS -3.1 ALOGPS pKa (Strongest Acidic) 4.73 Chemaxon pKa (Strongest Basic) -6 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 60.85 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 90.74 m3·mol-1 Chemaxon Polarizability 35.13 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9238 Caco-2 permeable + 0.5303 P-glycoprotein substrate Non-substrate 0.7216 P-glycoprotein inhibitor I Non-inhibitor 0.7803 P-glycoprotein inhibitor II Inhibitor 0.6587 Renal organic cation transporter Non-inhibitor 0.8981 CYP450 2C9 substrate Non-substrate 0.6167 CYP450 2D6 substrate Non-substrate 0.8844 CYP450 3A4 substrate Non-substrate 0.5538 CYP450 1A2 substrate Inhibitor 0.7253 CYP450 2C9 inhibitor Inhibitor 0.5 CYP450 2D6 inhibitor Non-inhibitor 0.923 CYP450 2C19 inhibitor Non-inhibitor 0.9035 CYP450 3A4 inhibitor Inhibitor 0.796 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6021 Ames test AMES toxic 0.9107 Carcinogenicity Non-carcinogens 0.7686 Biodegradation Not ready biodegradable 0.9847 Rat acute toxicity 2.9626 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9507 hERG inhibition (predictor II) Non-inhibitor 0.924
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 186.63911 predictedDeepCCS 1.0 (2019) [M+H]+ 189.1494 predictedDeepCCS 1.0 (2019) [M+Na]+ 197.55394 predictedDeepCCS 1.0 (2019)
Targets
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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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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]
- 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
- 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
- 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 at June 13, 2005 13:24 / Updated at February 20, 2024 23:55