CAS 129-20-4|Flegmostam|Butapirone|4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione|Infamil|P-hydroxyphenylbutazone|Hydroxyphenylbutazon|Iridil|Flogodin|Telidac|Rapostan|Ipabutona|Isobutil...

General Information

Structure

Molecular Formula

C₁₉H₂₀N₂O₃

Molecular Mass

324.3737

Exact Mass

324.14739251

Charge

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

InChIKey

HFHZKZSRXITVMK-UHFFFAOYSA-N

Canonic Smiles

CCCCC1C(=O)N(N(C1=O)c1ccc(cc1)O)c1ccccc1

Isomeric Smiles

O=C1N(N(C(=O)C1CCCC)c1ccccc1)c1ccc(O)cc1

Calculated Properties

JChem

LogD (pH = 7.4)

1.83

LogD (pH = 5.5)

3.01

Log P

3.83

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

4.73

Polar Surface Area

60.85

Polarizability

35.18

Molar Refractivity

90.74

LOG S

-4.37

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

Neo-farmadolIpabutonaFlogitoloFlogheneFlegmostamIridilTandalgesicIdrobutazinaPoliflogilFlanarilFlogodinButapironeReumoxFlopirinaMetabolite ITelidacButanovaInfammilPortorilGenalRemazinOxyphentaminTanderilDefloginInfamilOxazolidinIsobutilOxazolioinRapostanRumapaxAradinumButafloginOxi-fenibutolOxibutolFlogorilMysiteEtrozolidinaPirabutinaTanderalReunabutalCinophen-nOxazolidin-geigyOptimalPirafloginTelidalIsobutazinaCalifornitVisubutinaButanoraTandearilTandacoteTendearilOxalidFlogalOxybutonOffitrilNeofenArtroflogButileneFrabelFlogistinFlogostopValioilCrovarilButazonicFlamaril

Synonyms

3,5-Pyrazolidinedione, 4-butyl-1-(4-hydroxyphenyl)-2-phenyl4-Butyl-2-(p-hydroxyphenyl)-1-phenyl-3,5-pyrazolidinedione1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-butylpyrazolidine4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedioneP-hydroxyphenylbutazoneHydroxyphenylbutazonOssifenbutazone [dcit]1-p-Hydroxyphenyl-2-phenyl-3,5-dioxo-4-N-butylpyrazolidineUsaf Ge-14OPBOxyphenbutazoneOxiphenbutazonumOxyphenobutazone1-(p-Hydroxyphenyl)-2-phenyl-4-butyl-3,5-pyrazolidinedioneOxifenylbutazon4-Butyl-1-(p-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedioneOxiphenbutazoneOxyphenbutazonum [inn-latin]Oxyphenylbutazone4-Butyl-2-(4-hydroxyphenyl)-1-phenyl-3,5-dioxopyrazolidineOxifenbutazona [inn-spanish]P-oxyphenylbutazoneRapostanCrovarilVisubutinaCalifornitButapironeOxyphenylbutazone1-(p-Hydroxyphenyl)-2-phenyl-4-butyl-3,5-pyrazolidinedioneOxifenylbutazonp-Hydroxyphenylbutazoneoxyphenbutazone4-Butyl-1-(p-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione4-Butyl-2-(4-hydroxyphenyl)-1-phenyl-3,5-dioxopyrazolidine4-Butyl-2-(p-hydroxyphenyl)-1-phenyl-3,5-pyrazolidinedione4-Butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedionep-OxyphenylbutazoneHydroxyphenylbutazon1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-n-butylpyrazolidine3,5-Dioxo-1-phenyl-2-(p-hydroxyphenyl)-4-N-butylpyrazolideneOxiphenbutazonumOxi-fenibutol1-Phenyl-2-(p-hydroxyphenyl)-3,5-dioxo-4-butylpyrazolidine

IUPAC name

4-butyl-1-(4-hydroxyphenyl)-2-phenylpyrazolidine-3,5-dione

IUPAC Traditional name

cinophen-N oxyphenbutazone

API Name

Oxyphenbutazone

International Nonproprietary Name (INN)

oxyphenbutazonumoxyphenbutazoneoxifenbutazona

Names and Identifiers

Registration numbers

PubChem SID

16096668846507285170474386

PubChem CID

CAS Number

DrugBank ID

Reaxys Registry

PubMed Citation Links

1222682189639851916166883585950154673689667309664141661689437928622906860567143457812398301376615720299217214287587001487380595661771154685723012453

BRENDA Ligand Database

165883

BRENDA Database

1.1.1.2133.1.1.4

KEGG ID

C19494

MetaboLights Database

MTBLS2291MTBLS804MTBLS2224

Patent number

WO2005107748US2008014272EP642336

BindingDB Database

200298

CHEBI ID

CHEBI:76258

CHEMBL

CHEMBL1228

Drug Central Database

CompTox Database

LINCS Database

ACToR Database

BKMS React Database

KEGG DRUG Database

SureChEMBL Database

Wikipedia Title

Registration numbers

Properties

Physical Property

Solubility

0.06 mg/mL at 30 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]

Methanol

Chloroform

Hydrophobicity(logP)

2.72 [HANSCH,C ET AL. (1995)]

Apperance

Light Beige Solid

Melting Point

109-111°C

Product Information

Certificate of Analysis

Download link

Safety Information

MSDS Link

Download link

Storage Condition

Hygroscopic, -20°C Freezer, Under Inert Atmosphere

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB03585

Drug Groups

experimental; withdrawn

Description

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

External Links

• [Wikipedia]

TRC

O876950

Anti-inflammatory.

ChEBI

CHEBI:76258

A metabolite of phenylbutazone obtained by hydroxylation at position 4 of one of the phenyl rings. Commonly used (as its hydrate) to treat pain, swelling and stiffness associated with arthritis and gout, it was withdrawn from the market 1984 following association with blood dyscrasis and Stevens-Johnson syndrome.

Molecule Details

References

PubChem Literature

From Data Sources

• Yoshida, F., et al.: J. Med. Chem., 43, 2575 (2000)

• Chen, M., ET AL.: Pharm. Res., 18, 1645 (2000)

• Davis, A., et al.: Curr. Opin. Chem. Biol., 8, 378 (2000)

• Wang, J., ET AL.: Anal. Chim. Acta, 601, 156 (2000)

References

Bioactivity

PubChem BioAssay

Bioactivity