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Identification
NameOxyphenbutazone
Accession NumberDB03585  (EXPT02440)
TypeSmall Molecule
GroupsWithdrawn
Description

Oxyphenbutazone was withdrawn from the Canadian market in March 1985 due to concerns regarding bone marrow suppression.

Structure
Thumb
Synonyms
Oxifenbutazona
Oxiphenbutazone
Oxyphenbutazonum
External Identifiers
  • USAF Ge-14
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Oxybutazone Tab 100mgtablet100 mgoralIcn Canada Ltd.1981-12-312005-04-26Canada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Oxyphenbutazone 100mg Tabletstablet100 mgoralLaboratoires Confab IncNot applicableNot applicableCanada 5f16b84899037e23705f146ff57e3794121879cb055f0954756d94bc690476b4
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
OxyphenbutazoneNot Available
ReozonNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number129-20-4
WeightAverage: 324.3737
Monoisotopic: 324.147392516
Chemical FormulaC19H20N2O3
InChI KeyInChIKey=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
Taxonomy
ClassificationNot classified
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tabletoral100 mg
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 Solubility0.256 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesM01AA03M02AA04S01BC02
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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 December 08, 2015 16:02