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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyOxyphenbutazone
Identification
- Name
- Oxyphenbutazone
- Accession Number
- DB03585 (EXPT02440)
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Description
Oxyphenbutazone was withdrawn from the Canadian market in March 1985 due to concerns regarding bone marrow suppression.
- Structure
Structure for Oxyphenbutazone (DB03585)
- Synonyms
- Oxifenbutazona
- Oxiphenbutazone
- Oxyphenbutazonum
- External IDs
- USAF Ge-14
- Product Ingredients
Ingredient UNII CAS InChI Key Oxyphenbutazone monohydrate H806S4B3NS 7081-38-1 CNDQSXOVEQXJOE-UHFFFAOYSA-N - Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Oxybutazone Tab 100mg Tablet 100 mg Oral Icn Pharmaceuticals 1981-12-31 2005-04-26 Canada 
Oxyphenbutazone 100mg Tablets Tablet 100 mg Oral Laboratoires Confab Inc Not applicable Not applicable Canada - International/Other Brands
- Oxyphenbutazone / Reozon
- Categories
- Agents causing hyperkalemia
- 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
- Butylpyrazolidines
- Central Nervous System Agents
- Musculo-Skeletal System
- Nephrotoxic agents
- Ophthalmologicals
- Other Nonsteroidal Antiimflammatory Agents
- Peripheral Nervous System Agents
- Pyrazoles
- Pyrazolones
- Sensory Organs
- Sensory System Agents
- Topical Products for Joint and Muscular Pain
- UNII
- A7D84513GV
- CAS number
- 129-20-4
- Weight
- Average: 324.3737
Monoisotopic: 324.147392516 - Chemical Formula
- C19H20N2O3
- 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
Pharmacology
- Indication
- Not Available
- Pharmacodynamics
- Not Available
- Mechanism of action
Target Actions Organism UGroup IIE secretory phospholipase A2 Not Available Human - 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
- Toxicity
- Not Available
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (4R)-limonene The risk or severity of adverse effects can be increased when Oxyphenbutazone is combined with (4R)-limonene. 16-Bromoepiandrosterone The risk or severity of adverse effects can be increased when Oxyphenbutazone is combined with 16-Bromoepiandrosterone. 19-norandrostenedione The risk or severity of adverse effects can be increased when Oxyphenbutazone is combined with 19-norandrostenedione. 5-androstenedione The risk or severity of adverse effects can be increased when Oxyphenbutazone is combined with 5-androstenedione. 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. Acetaminophen Oxyphenbutazone may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetylsalicylic acid The risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Oxyphenbutazone. Acyclovir Oxyphenbutazone may decrease the excretion rate of Acyclovir which could result in a higher serum level. - Food Interactions
- Take with food to reduce irritation.
References
- General References
- Not Available
- External Links
- KEGG Compound
- C19494
- PubChem Compound
- 4641
- PubChem Substance
- 46507285
- ChemSpider
- 4480
- BindingDB
- 200298
- ChEBI
- 76258
- ChEMBL
- CHEMBL1228
- PharmGKB
- PA450750
- HET
- OPB
- Wikipedia
- Oxyphenbutazone
- ATC Codes
- S01BC02 — Oxyphenbutazone
- S01BC — Antiinflammatory agents, non-steroids
- S01B — ANTIINFLAMMATORY AGENTS
- S01 — OPHTHALMOLOGICALS
- S — SENSORY ORGANS
- M01AA — Butylpyrazolidines
- M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
- M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
- M — MUSCULO-SKELETAL SYSTEM
- AHFS Codes
- 28:08.04.92 — Other Nonsteroidal Antiimflammatory Agents
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
Form Route Strength Tablet Oral 100 mg - 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) 4.87 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 35.14 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
Spectrum Spectrum Type Splash Key GC-MS Spectrum - EI-B GC-MS splash10-0006-9601000000-0e93b2309b6f4ff21792 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-0002-3920000000-8a5be556648d9ff3213b
Taxonomy
- 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-hydroxy-2-unsubstituted benzenoid / Monocyclic benzene moiety / Pyrazolidinone / 1,3-dicarbonyl compound / Pyrazolidine / Carboxylic acid hydrazide / Azacycle / Organoheterocyclic compound / Carboxylic acid derivative / Organic oxide
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- phenols, pyrazolidines (CHEBI:76258)
Targets
- Kind
- Protein
- Organism
- Human
- 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. [PubMed:17139284]
- 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. [PubMed:17016423]
- 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. [PubMed:10592235]
Carriers
- Kind
- Protein
- Organism
- Human
- 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. [PubMed:9275312]
Transporters
- Kind
- Protein
- Organism
- Human
- 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. [PubMed:10220563]
Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 08:37