OXYPURINOL

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C5H4N4O2
Molecular Weight	152.1109
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C1NC2=C(C=NN2)C(=O)N1

InChI

InChIKey=HXNFUBHNUDHIGC-UHFFFAOYSA-N

InChI=1S/C5H4N4O2/c10-4-2-1-6-9-3(2)7-5(11)8-4/h1H,(H3,6,7,8,9,10,11)

HIDE SMILES / InChI

Molecular Formula	C5H4N4O2
Molecular Weight	152.1109
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22300439 | https://www.ncbi.nlm.nih.gov/pubmed/5658870 | https://www.ncbi.nlm.nih.gov/pubmed/15139781 | https://adisinsight.springer.com/drugs/800016266

Oxypurinol is an active metabolite of allopurinol and is an inhibitor of xanthine oxidase. Cardiome Pharma developed oxipurinol for the treatment of allopurinol-intolerant hyperuricemia (gout) and for the treatment of congestive heart failure. It is known, that inhibition of xanthine oxidase can improve myocardial work efficiency by sensitizing cardiac muscle cells to calcium ions, which are a key determinant of cardiac muscle function. However, all these studied were discontinued.

Approval Year

PubMed

Title	Date	PubMed
Sodium nitroprusside-induced seizure and taurine release from rat hippocampus.	2000	11140358
Photoreactivation of alloxanthine-inhibited xanthine oxidase.	2001 Apr	11332041
Effect of furosemide on renal excretion of oxypurinol and purine bases.	2001 Feb	11229436
Characterization of the magnitude and kinetics of xanthine oxidase-catalyzed nitrite reduction. Evaluation of its role in nitric oxide generation in anoxic tissues.	2001 Jul 6	11312267
Does xanthine oxidase contribute to the hydroxyl radical generation in ischemia and reperfusion of the cochlea?	2001 Mar	11223291
Elevated superoxide production by active H-ras enhances human lung WI-38VA-13 cell proliferation, migration and resistance to TNF-alpha.	2001 Mar 22	11313892
[Hypersensitivity syndrome during therapy with allopurinol in asymptomatic hyperuricemia with a fatal outcome].	2001 Nov 23	11719858
Effect of fenofibrate on plasma concentration and urinary excretion of purine bases and oxypurinol.	2001 Oct	11669172
Effect of norepinephrine on the urinary excretion of purine bases and oxypurinol.	2001 Oct	11586499
Ischemia-reperfusion injury of retinal endothelium by cyclooxygenase- and xanthine oxidase-derived superoxide.	2002 Apr	12076093
Further studies on the use of allopurinol to reduce plasma uric acid concentrations in the Red-tailed Hawk (Buteo jamaicensis) hyperuricaemic model.	2002 Dec	12593739
Xanthine oxidase-catalyzed metabolism of 2-nitrofluorene, a carcinogenic air pollutant, in rat skin.	2003 Apr	12642461
Deferoxamine, allopurinol and oxypurinol are not neuroprotective after oxygen/glucose deprivation in an organotypic hippocampal model, lacking functional endothelial cells.	2003 Feb 14	12560112
Oxypurinol administration fails to prevent hypoxic-ischemic brain injury in neonatal rats.	2003 Feb 15	12576142
Confirmation of superoxide generation via xanthine oxidase in streptozotocin-induced diabetic mice.	2003 Jul	12911273
Facile and rapid high-performance liquid chromatography method for simultaneous determination of allopurinol and oxypurinol in human serum.	2003 Jun	12795781
Determination of allopurinol by micelle-stabilised room-temperature phosphorescence in real samples.	2003 Jun 1	12763532
Ischaemia-reperfusion injury in photodynamic therapy-treated mouse tumours.	2003 Mar 10	12618887
Effect of allopurinol pretreatment on free radical generation after primary coronary angioplasty for acute myocardial infarction.	2003 May	12717099
Nitric oxide -- superoxide cooperation in the regulation of renal Na(+),K(+)-ATPase.	2004	15625565
Oxipurinol: alloxanthine, Oxyprim, oxypurinol.	2004	15139781
Liquid chromatographic method for the determination of uridine in human serum.	2004 Apr 25	15063346
Effect of simultaneous inhibition of TNF-alpha production and xanthine oxidase in experimental acute pancreatitis: the role of mitogen activated protein kinases.	2004 Jul	15213626
Stable compounds of cigarette smoke induce endothelial superoxide anion production via NADPH oxidase activation.	2004 Jun	15059808
Race-specific differences in endothelial function: predisposition of African Americans to vascular diseases.	2004 Jun 1	15159296
Insulin generates free radicals by an NAD(P)H, phosphatidylinositol 3'-kinase-dependent mechanism in human skin fibroblasts ex vivo.	2004 May	15111505
Potential role of mycophenolate mofetil in the management of neuroblastoma patients.	2004 Oct	15571295
Pharmacology of drugs for hyperuricemia. Mechanisms, kinetics and interactions.	2005	15604604
Atrial fibrillation increases production of superoxide by the left atrium and left atrial appendage: role of the NADPH and xanthine oxidases.	2005 Aug 30	16129811
Chronic heart failure: an overview of conventional treatment versus novel approaches.	2005 Dec	16306919
Involvement of uric acid transporter in increased renal clearance of the xanthine oxidase inhibitor oxypurinol induced by a uricosuric agent, benzbromarone.	2005 Dec	16135657
A defect of neuronal nitric oxide synthase increases xanthine oxidase-derived superoxide anion and attenuates the control of myocardial oxygen consumption by nitric oxide derived from endothelial nitric oxide synthase.	2005 Feb 18	15637297
Sulfonylurea as well as elevated glucose levels stimulate reactive oxygen species production in the pancreatic beta-cell line, MIN6-a role of NAD(P)H oxidase in beta-cells.	2005 Jan 7	15567152
Vascular ossification-calcification in metabolic syndrome, type 2 diabetes mellitus, chronic kidney disease, and calciphylaxis-calcific uremic arteriolopathy: the emerging role of sodium thiosulfate.	2005 Mar 18	15777477
Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection.	2005 May 25	15833286
Comparative substrate recognition by bacterial and fungal purine transporters of the NAT/NCS2 family.	2005 May-Jun	16096268
Oxypurinol improves coronary and peripheral endothelial function in patients with coronary artery disease.	2005 Nov 1	16214034
Allopurinol or oxypurinol in heart failure therapy - a promising new development or end of story?	2005 Oct	16382292
Involvement of molybdenum hydroxylases in reductive metabolism of nitro polycyclic aromatic hydrocarbons in mammalian skin.	2005 Sep	15932950
A concise history of gout and hyperuricemia and their treatment.	2006	16820040
Xanthine oxidoreductase inhibition causes reverse remodeling in rats with dilated cardiomyopathy.	2006 Feb 3	16357304
Plasma concentrations and urinary excretion of purine bases (uric acid, hypoxanthine, and xanthine) and oxypurinol after rigorous exercise.	2006 Jan	16324927
Micellar electrokinetic capillary chromatographic method for the quantitative analysis of uricosuric and antigout drugs in pharmaceutical preparations.	2006 Jun	16718644
Superoxide radical production by allopurinol and xanthine oxidase.	2006 Jun 14	16650385
Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol.	2006 Mar	16507884
TNF-alpha contributes to endothelial dysfunction in ischemia/reperfusion injury.	2006 Mar	16385082
[Genetically determined gout: characteristics of the course].	2006 May-Jun	16933856
Clinical trials update from the Heart Failure Society of America meeting: FIX-CHF-4, selective cardiac myosin activator and OPT-CHF.	2006 Nov	17049305
Inhibition of xanthine oxidase improves myocardial contractility in patients with ischemic cardiomyopathy.	2006 Oct 15	17015175
The effect of xanthine oxidase inhibition upon ejection fraction in heart failure patients: La Plata Study.	2006 Sep	16952781

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:36:54 GMT 2025` Edited by `admin` on `Mon Mar 31 17:36:54 GMT 2025`
Record UNII	G97OZE5068
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXYPURINOL

Official Name

English

OXIPURINOL

Preferred Name

English

NSC-76239

Code

English

Oxipurinol [WHO-DD]

Common Name

English

1H-PYRAZOLO(3,4-D)PYRIMIDINE,4,6(5H,7H)-DIONE

Common Name

English

OXYPURINOL [USAN]

Common Name

English

1H-Pyrazolo[3,4-d]pyrimidine-4,6-diol

Systematic Name

English

oxipurinol [INN]

Common Name

English

Classification Tree Code System Code

LOINC

75132-1