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Identification
NameOxyphenbutazone
Accession NumberDB03585  (EXPT02440)
TypeSmall Molecule
GroupsExperimental, Withdrawn
Description

Oxyphenbutazone was withdrawn from the Canadian market in March 1985 due to concerns regarding bone marrow suppression.

Structure
Thumb
Synonyms
SynonymLanguageCode
OxifenbutazonaSpanishNot Available
OxiphenbutazoneNot AvailableNot Available
OxyphenbutazonumLatinNot Available
SaltsNot Available
Brand names
NameCompany
OxyphenbutazoneNot Available
ReozonNot Available
Brand mixturesNot Available
Categories
CAS number129-20-4
WeightAverage: 324.3737
Monoisotopic: 324.147392516
Chemical FormulaC19H20N2O3
InChI KeyHFHZKZSRXITVMK-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenols and Derivatives
Direct parentAminophenols
Alternative parentsPyrazolidinones; Carboxylic Acid Hydrazides; Polyamines; Enols; Carboxylic Acid Amides; Hydrazines and Derivatives
Substituentspyrazolidinone; pyrazolidine; carboxamide group; carboxylic acid hydrazide; carboxylic acid derivative; enol; polyamine; hydrazine derivative; organonitrogen compound; amine
Classification descriptionThis compound belongs to the aminophenols. These are organic compounds containing an amino group attached to a phenol.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Inhibitor 0.5
CYP450 2D6 substrate Non-inhibitor 0.923
CYP450 2C19 substrate Non-inhibitor 0.9035
CYP450 3A4 substrate 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
Pharmacoeconomics
Manufacturers
  • Watson laboratories inc
  • Novartis pharmaceuticals corp
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point96 °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 Solubility0.256ALOGPS
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
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound4641
PubChem Substance46507285
ChemSpider4480
PharmGKBPA450750
HETOPB
WikipediaOxyphenbutazone
ATC CodesM02AA04S01BC02M01AA03
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcenocoumarolThe NSAID, oxyphenbutazone, may increase the anticoagulant effect of acenocoumarol.
AlendronateIncreased risk of gastric toxicity
AnisindioneThe NSAID, oxyphenbutazone, may increase the anticoagulant effect of anisindione.
DicoumarolThe NSAID, oxyphenbutazone, may increase the anticoagulant effect of dicumarol.
EthotoinThe NSAID, oxyphenbutazone, may increase the hydantoin effect of ethotoin.
FosphenytoinThe NSAID, oxphenbutazone, may increase the hydantoin effect of fosphenytoin.
MephenytoinThe NSAID, oxyphenbutazone, may increase the hydantoin effect of mephenytoin.
PhenytoinThe NSAID, oxphenbutazone, may increase the therapeutic and adverse effects of phenytoin.
WarfarinThe NSAID, oxyphenbutazone, may increase the anticoagulant effect of warfarin.
Food Interactions
  • Take with food to reduce irritation.

Targets

1. Group IIE secretory phospholipase A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Group IIE secretory phospholipase A2 Q9NZK7 Details

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. Pubmed
  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. Pubmed
  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. Pubmed

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Bertucci C, Wainer IW: Improved chromatographic performance of a modified human albumin based stationary phase. Chirality. 1997;9(4):335-40. Pubmed

Transporters

1. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

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. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:21