Oxipurinol

Oxipurinol Basic information
Product Name:Oxipurinol
Synonyms:4,6-Dihydroxy-1H-pyrazolo[3,4-d]pyrimidine, 98+%;4,6-Dihydropyrazolo Pyrimidine;4,6-Dihydroxypyrazolo[3,4-d]pyrimidine,99%;4,6-Dihydroxypyrazolo[3,4-d]pyriMidine (Oxypurinol);OXYPURINOL;OXIPURINOL;4,6-Dihydroxy-1H-pyrazolo[3,4-d]pyrimidine;4,6-Dioxopyrazolo[3,4-d]pyrimidine
CAS:2465-59-0
MF:C5H4N4O2
MW:152.11
EINECS:219-570-9
Product Categories:Heterocycles, Metabolites & Impurities, Nucleotides, Bases & Related Reagents, Pharmaceuticals, Intermediates & Fine Chemicals;Heterocycles;Bases & Related Reagents;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Pyridines, Pyrimidines, Purines and Pteredines;Nucleotides and Nucleosides;Nucleotides;Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
Mol File:2465-59-0.mol
Oxipurinol Structure
Oxipurinol Chemical Properties
Melting point 300 °C
Boiling point 274.55°C (rough estimate)
density 1.637
refractive index 1.8500 (estimate)
storage temp. Sealed in dry,Room Temperature
solubility Soluble in DMSO.
pkapKa 7.7 (Uncertain)
form Powder
color Light yellow
BRN 139956
Stability:Hygroscoipic
CAS DataBase Reference2465-59-0(CAS DataBase Reference)
EPA Substance Registry SystemOxypurinol (2465-59-0)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 36
WGK Germany 3
HazardClass IRRITANT
HS Code 29335990
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
Oxipurinol Usage And Synthesis
Chemical PropertiesOff White Solid
UsesA metabolite of Allopurinol.
Uses4,6-Dihydroxy-1H-pyrazolo[3,4-d]pyrimidine is an inhibitor to study the specificity and kinetics of xanthine oxidase. It is also used as an anti-inflammatory agent via inhibition of xanthine oxidase.
UsesOxypurinol, an allopurinol metabolite, is used as an inhibitor to study the specificity and kinetics of of xanthine oxidase(s). Oxypurinol is also used as an anti-inflammatory agent via inhibition of xanthine oxidase.
DefinitionChEBI: A pyrazolopyrimidine that is 4,5,6,7-tetrahydro-H-pyrazolo[3,4-d]pyrimidine substituted by oxo groups at positions 4 and 6.
Biological Activityoxipurinol is a xanthine oxidoreductase inhibitor.xanthine oxidoreductase (xo), a complex molybdoflavoenzyme present in milk and many other tissues, has been studied for many years. xo is generally recognized as a critical enzyme in purine catabolism.
Biochem/physiol ActionsAn allopurinol metabolite.
in vitroallopurinol could be rapidly oxidized by xo to its active metabolite oxypurinol (both isosteres of hypoxanthine and xanthine, respectively), which also could inhibit xo. oxypurinol was identified as a noncompetitive inhibitor of xo; the formation of this compound was reported to be responsible for much of the pharmacological activity of allopurinol. moreover, both allopurinol and oxypurinol showed free radical scavenging effects in isolated hearts, and exerted cardioprotective effects despite no detectable xo activities [1].
in vivoanimal study found that in the vasculature of hypercholesterolemic rabbits, oxypurinol treatment led to a decrease in vascular free radical production [1].
references[1] p. pacher, a. nivorozhkin and c. szabó. therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. pharmacological reviews 58(1), 87-114 (2006).
[2] day ro, graham gg, hicks m, mclachlan aj, stocker sl, williams km. clinical pharmacokinetics and pharmacodynamics of allopurinol and oxypurinol. clin pharmacokinet. 2007;46(8):623-44.
2,6-Dihydroxypurine 3-PHENYL-5,7-DIHYDROXYPYRAZOLO(1,5-A)PYRIMIDINE BUTTPARK 57\40-45 Guanine 1-[3-CHLORO-5-(TRIFLUOROMETHYL)-2-PYRIDINYL]-1H-PYRAZOLO[3,4-D]PYRIMIDINE-4,6(5H,7H)-DIONE Oxipurinol 6-Hydroxypurine Guanine hydrochloride Purine 6-Mercaptopurine monohydrate 8-Bromoguanosine 1-PHENYL-1H-PYRAZOLO[3,4-D]PYRIMIDINE-4,6(5H,7H)-DIONE 1-BENZYL-5-PHENYL-1,7-DIHYDRO-PYRAZOLO[3,4-D]PYRIMIDINE-4,6-DIONE ETHYL 5,7-DIHYDROXYPYRAZOLO[1,5-A]PYRIMIDINE-3-CARBOXYLATE 9-[(2-Acetoxyethoxy)methyl]-N2-acetylguanine Uric acid 2-Thioxanthine Allopurinol

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