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
Clinical trials update from the Heart Failure Society of America meeting: FIX-CHF-4, selective cardiac myosin activator and OPT-CHF.	2006-11	17049305
Inhibition of xanthine oxidase improves myocardial contractility in patients with ischemic cardiomyopathy.	2006-10-15	17015175
The effect of xanthine oxidase inhibition upon ejection fraction in heart failure patients: La Plata Study.	2006-09	16952781
[Genetically determined gout: characteristics of the course].	2006-08-29	16933856
Chemo- and regioselective functionalization of uracil derivatives. Applications to the synthesis of oxypurinol and emivirine.	2006-08-17	16898805
[The current concepts of functional role of carotenoids in the eukaryotic chloroplasts].	2006-07-26	16862869
Century-long synchrony of fossil algae in a chain of Canadian prairie lakes.	2006-07	16922321
Superoxide radical production by allopurinol and xanthine oxidase.	2006-06-14	16650385
Micellar electrokinetic capillary chromatographic method for the quantitative analysis of uricosuric and antigout drugs in pharmaceutical preparations.	2006-06	16718644
Effects of allopurinol on beer-induced increases in plasma concentrations and urinary excretion of purine bases (uric acid, hypoxanthine, and xanthine).	2006-03	16673211
Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol.	2006-03	16507884
Acute depletion of reduced glutathione causes extensive carbonylation of rat brain proteins.	2006-03	16447283
TNF-alpha contributes to endothelial dysfunction in ischemia/reperfusion injury.	2006-03	16385082
Acute inhibition of the endogenous xanthine oxidase improves renal hemodynamics in hypercholesterolemic pigs.	2006-03	16284087
Xanthine oxidoreductase inhibition causes reverse remodeling in rats with dilated cardiomyopathy.	2006-02-03	16357304
Xanthine oxidase inhibitors improve energetics and function after infarction in failing mouse hearts.	2006-02	16183726
Plasma concentrations and urinary excretion of purine bases (uric acid, hypoxanthine, and xanthine) and oxypurinol after rigorous exercise.	2006-01	16324927
Recent developments in our understanding of the renal basis of hyperuricemia and the development of novel antihyperuricemic therapeutics.	2006	16820043
A concise history of gout and hyperuricemia and their treatment.	2006	16820040
Chronic heart failure: an overview of conventional treatment versus novel approaches.	2005-12	16306919
Involvement of uric acid transporter in increased renal clearance of the xanthine oxidase inhibitor oxypurinol induced by a uricosuric agent, benzbromarone.	2005-12	16135657
Oxypurinol improves coronary and peripheral endothelial function in patients with coronary artery disease.	2005-11-01	16214034
Allopurinol or oxypurinol in heart failure therapy - a promising new development or end of story?	2005-10	16382292
Allopurinol-induced DRESS syndrome.	2005-10	16259349
Role of oxidative stress in angiotensin-II mediated contraction of human conduit arteries in patients with cardiovascular disease.	2005-10	16243586
Gateways to clinical trials.	2005-09-24	16179960
Involvement of molybdenum hydroxylases in reductive metabolism of nitro polycyclic aromatic hydrocarbons in mammalian skin.	2005-09	15932950
Atrial fibrillation increases production of superoxide by the left atrium and left atrial appendage: role of the NADPH and xanthine oxidases.	2005-08-30	16129811
Comparative substrate recognition by bacterial and fungal purine transporters of the NAT/NCS2 family.	2005-08-13	16096268
Cloning and functional characterization of two bacterial members of the NAT/NCS2 family in Escherichia coli.	2005-08-13	16096267
Appropriate dosing regimen of allopurinol in Japanese patients.	2005-08	15985055
Transplacental effects of allopurinol on suppression of oxygen free radical production in chronically instrumented fetal lamb brains during intermittent umbilical cord occlusion.	2005-07	16105785
Simultaneous determination of 16 purine derivatives in urinary calculi by gradient reversed-phase high-performance liquid chromatography with UV detection.	2005-05-25	15833286
Vascular ossification-calcification in metabolic syndrome, type 2 diabetes mellitus, chronic kidney disease, and calciphylaxis-calcific uremic arteriolopathy: the emerging role of sodium thiosulfate.	2005-03-18	15777477
Selectivity of febuxostat, a novel non-purine inhibitor of xanthine oxidase/xanthine dehydrogenase.	2005-03-04	15698861
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.	2005-02-18	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.	2005-01-07	15567152
Pharmacology of drugs for hyperuricemia. Mechanisms, kinetics and interactions.	2005	15604604
Rationale, design and organisation of an efficacy and safety study of oxypurinol added to standard therapy in patients with NYHA class III - IV congestive heart failure.	2004-11	15500398
Potential role of mycophenolate mofetil in the management of neuroblastoma patients.	2004-10	15571295
Are allopurinol and metabolites found in HPRT deficient erythrocytes responsible for increased NAD synthesis?	2004-10	15571228
Binding of xanthine oxidase to glycosaminoglycans limits inhibition by oxypurinol.	2004-09-03	15231841
Effect of simultaneous inhibition of TNF-alpha production and xanthine oxidase in experimental acute pancreatitis: the role of mitogen activated protein kinases.	2004-07	15213626
Race-specific differences in endothelial function: predisposition of African Americans to vascular diseases.	2004-06-01	15159296
Rationale for a new generation of indicators for coastal waters.	2004-06	15198917
Insulin generates free radicals by an NAD(P)H, phosphatidylinositol 3'-kinase-dependent mechanism in human skin fibroblasts ex vivo.	2004-05	15111505
Liquid chromatographic method for the determination of uridine in human serum.	2004-04-25	15063346
Nitric oxide -- superoxide cooperation in the regulation of renal Na(+),K(+)-ATPase.	2004	15625565
Management of acute and chronic gouty arthritis: present state-of-the-art.	2004	15481999
Oxipurinol: alloxanthine, Oxyprim, oxypurinol.	2004	15139781

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