23111-33-3

Basic information

• Product Name: SUXIBUZONE IMPURITY C
• Synonyms: SUXIBUZONE IMPURITY C;4-Butyl-4-(hydroxymethyl)-1,2-diphenyl-1,2-dihydro-4H-pyrazole-3,5-dione;4-Hydroxymethylphenylbutazone
• CAS NO: 23111-33-3
• Molecular Formula: C₂₀H₂₂N₂O₃
• Molecular Weight: 338.40028
• Mol File: 23111-33-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 473.3°Cat760mmHg
• Flash Point: 240°C
• Appearance: /
• Density: 1.209g/cm³
• Vapor Pressure: 9.22E-10mmHg at 25°C
• Refractive Index: 1.593
• CAS DataBase Reference: SUXIBUZONE IMPURITY C(CAS DataBase Reference)
• NIST Chemistry Reference: SUXIBUZONE IMPURITY C(23111-33-3)
• EPA Substance Registry System: SUXIBUZONE IMPURITY C(23111-33-3)

Safety Data

• Hazardous Substances Data: 23111-33-3(Hazardous Substances Data)

Usage

Uses

4-Hydroxymethylphenylbutazone is an intermediate in the synthesis of Suxibuzone (S880000) which is a prodrug of the non steroidal anti inflammatory drug phenylbutazone. It is a drug used for joint and muscular pain.

InChI:InChI=1/C20H22N2O3/c1-2-3-14-20(15-23)18(24)21(16-10-6-4-7-11-16)22(19(20)25)17-12-8-5-9-13-17/h4-13,23H,2-3,14-15H2,1H3

Upstream product

• 50-00-0 formaldehyd 
• 50-33-9 Phenylbutazone 

Downstream Products

• 77117-57-8 4-butyl-4-morpholinomethyl-1,2-diphenyl-pyrazolidine-3,5-dione 
• 76383-59-0 4-Butyl-4-(4-methyl-piperidin-1-ylmethyl)-1,2-diphenyl-pyrazolidine-3,5-dione 
• 76383-64-7 4-Butyl-4-(3,4-dihydro-1H-isoquinolin-2-ylmethyl)-1,2-diphenyl-pyrazolidine-3,5-dione 
• 1229521-07-6 4-butyl-4-((methylthiomethoxy)methyl)-1,2-diphenylpyrazolidine-3,5-dione 
• 16860-43-8 4-Butyl-4-hydroxy-1,2-diphenyl-1H-pyrazol-3,5(2H,4H)-dion 
• 50-33-9 Phenylbutazone 
• 1229645-20-8 C₂₁H₂₅N₂O₇P 
• 1229521-08-7 dibenzyl ((4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)methoxy)methyl phosphate 
• 1229645-19-5 C₂₀H₂₃N₂O₆P 
• 74460-92-7 4-Butyl-4-[(2,3-dimethyl-phenylamino)-methyl]-1,2-diphenyl-pyrazolidine-3,5-dione 
• 76383-65-8 4-Butyl-4-[(4-fluoro-phenylamino)-methyl]-1,2-diphenyl-pyrazolidine-3,5-dione 
• 74460-99-4 4-(Benzylamino-methyl)-4-butyl-1,2-diphenyl-pyrazolidine-3,5-dione 
• 74461-02-2 4-Butyl-1,2-diphenyl-4-(o-tolylamino-methyl)-pyrazolidine-3,5-dione 
• 74460-95-0 4-Butyl-4-[(3-chloro-4-methyl-phenylamino)-methyl]-1,2-diphenyl-pyrazolidine-3,5-dione 

Relevant articles and documents

A novel prodrug strategy for β-dicarbonyl carbon acids: Syntheses and evaluation of the physicochemical characteristics of C-phosphoryloxymethyl (POM) and phosphoryloxymethyloxymethyl (POMOM) prodrug derivatives

The C-phosphoryloxymethyl (POM) and phosphoryloxymethyloxymethyl (POMOM) prodrugs resulting from derivatization at the reactive α-carbon of β-dicarbonyl carbon acid drugs represent a unique approach for improving their chemical stability and aqueous solubility. This work evaluates the physicochemical and in vitro enzymatic bioconversion lability of selected prodrugs of phenylbutazone and phenindione. The POM and POMOM prodrug derivatives of phenylbutazone are highly water soluble (≥250 mg/mL), chemically stable with projected shelf-lives of 4.5 years (pH 3.5, 258C) and 1.1 years (pH 6.0, 25°C), respectively. Interestingly, both prodrug derivatives do not display a pH-dependency typical of many phosphate monoesters, although the similarities of their apparent thermodynamic activation parameters indicate a hydrolysis mechanism similar to other phosphates. These prodrugs undergo alkaline phosphatases catalyzed bioconversion to their respective carbon acids with an expected faster rate exhibited by the POMOM derivatives. Additionally, in marked contrast to the oxidative instability of phenindione, its POM prodrug is stable. The results from these studies reaffirm the rationale of transiently "masking" the reactive a-carbon/proton bond by covalently incorporating a POM or POMOM promoiety. This prodrug strategy presents a twofold advantage, enhancement of aqueous solubility and prevention of oxidative instability, two intrinsic formulation limitations found for β-dicarbonyl carbon acid drugs.

Derivatives of 1,2-diphenyl-4-hydroxymethyl-3,5-dioxopyrazolidine and various structurally related compounds

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