DrugBank: Oxyphenbutazone (DB03585)

targets (1) transporters (1) carriers (1)

Identification

Name

Oxyphenbutazone

Accession Number

DB03585 (EXPT02440)

Type

small molecule

Groups

experimental, withdrawn

Description

Oxyphenbutazone was withdrawn from the Canadian market in March 1985 due to concerns regarding bone marrow suppression.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

1-(p-Hydroxyphenyl)-2-phenyl-4-butyl-3,5-pyrazolidinedione
1-p-Hydroxyphenyl-2-phenyl-3,5-dioxo-4-N-butylpyrazolidine
1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-butylpyrazolidine
3,5-Pyrazolidinedione, 4-butyl-1-(4-hydroxyphenyl)-2-phenyl
4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione
4-Butyl-1-(p-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione
4-Butyl-2-(4-hydroxyphenyl)-1-phenyl-3,5-dioxopyrazolidine
4-Butyl-2-(p-hydroxyphenyl)-1-phenyl-3,5-pyrazolidinedione
Hydroxyphenylbutazon
OPB
Ossifenbutazone [dcit]
Oxifenbutazona [inn-spanish]
Oxifenylbutazon
Oxiphenbutazone
Oxiphenbutazonum
Oxyphenbutazonum [inn-latin]
Oxyphenobutazone
Oxyphenylbutazone
P-hydroxyphenylbutazone
P-oxyphenylbutazone
Usaf Ge-14

Brand names

Aradinum
Artroflog
Butaflogin
Butanora
Butanova
Butapirone
Butazonic
Butilene
Californit
Cinophen-n
Crovaril
Deflogin
Etrozolidina
Flamaril
Flanaril
Flegmostam
Flogal
Floghene
Flogistin
Flogitolo
Flogodin
Flogoril
Flogostop
Flopirina
Frabel
Genal
Idrobutazina
Infamil
Infammil
Ipabutona
Iridil
Isobutazina
Isobutil
Metabolite I
Mysite
Neo-farmadol
Neofen
Offitril
Optimal
Oxalid
Oxazolidin
Oxazolidin-geigy
Oxazolioin
Oxi-fenibutol
Oxibutol
Oxybuton
Oxyphentamin
Pirabutina
Piraflogin
Poliflogil
Portoril
Rapostan
Remazin
Reumox
Reunabutal
Rumapax
Tandacote
Tandalgesic
Tandearil
Tanderal
Tanderil
Telidac
Telidal
Tendearil
Valioil
Visubutina

Brand name mixtures

Not Available

Categories

Phospholipase A2 Vrv-Pl-Viiia inhibitor

CAS number

129-20-4

Weight

Average: 324.3737
Monoisotopic: 324.147392516

Chemical Formula

C₁₉H₂₀N₂O₃

InChI Key

InChIKey=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

Plain Text

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

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

Not Available

Pharmacodynamics

Not Available

Mechanism of action

Not Available

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Not Available

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Watson laboratories inc
Novartis pharmaceuticals corp

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Melting point

96 oC

Experimental Properties

Property	Value	Source
water solubility	0.06 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
logP	2.72 [HANSCH,C ET AL. (1995)]	PhysProp
logS	-3.73 [ADME Research, USCD]	PhysProp

Predicted Properties

Property	Value	Source
water solubility	2.56e-01 g/l	ALOGPS
logP	2.79	ALOGPS
logP	3.83	ChemAxon Molconvert
logS	-3.10	ALOGPS
pKa	9.29	ChemAxon Molconvert
hydrogen acceptor count	3	ChemAxon Molconvert
hydrogen donor count	1	ChemAxon Molconvert
polar surface area	60.85	ChemAxon Molconvert
rotatable bond count	5	ChemAxon Molconvert
refractivity	90.74	ChemAxon Molconvert
polarizability	35.14	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
PubChem Compound	4641
PubChem Substance	46507285
ChemSpider	4480
PharmGKB	PA450750
HET	OPB
Drug Product Database	0
Wikipedia	http://en.wikipedia.org/wiki/Oxyphenbutazone

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

1Q7A

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Take with food to reduce irritation.

Targets
1. Group IIE secretory phospholipase A2 Pharmacological action: unknown PA2 catalyzes the calcium-dependent hydrolysis of the 2- acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids Organism class: human UniProt ID: Q9NZK7 Gene: PLA2G2E Protein Sequence: FASTA SNPs: SNPJam Report 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 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 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

Targets

1. Group IIE secretory phospholipase A2

Pharmacological action: unknown

PA2 catalyzes the calcium-dependent hydrolysis of the 2- acyl groups in 3-sn-phosphoglycerides. Has a preference for arachidonic-containing phospholipids

Organism class: human
UniProt ID: Q9NZK7 Link_out

Gene: PLA2G2E Link_out

Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

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
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
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

Transporters
1. Solute carrier family 22 member 6 Actions: inhibitor UniProt ID: Q4U2R8 Gene: hROAT1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report 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

Transporters

1. Solute carrier family 22 member 6

Actions: inhibitor
UniProt ID: Q4U2R8 Link_out

Gene: hROAT1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Carriers
1. Serum albumin 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 colloidal osmotic pressure of blood UniProt ID: P02768 Gene: ALB Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Bertucci C, Wainer IW: Improved chromatographic performance of a modified human albumin based stationary phase. Chirality. 1997;9(4):335-40. Pubmed

Carriers

1. Serum albumin

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 colloidal osmotic pressure of blood

UniProt ID: P02768 Link_out

Gene: ALB

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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

Comments

Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 14:46

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.