Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Oxypurinol
- DrugBank Accession Number
- DB05262
- Background
Oxypurinol, an inhibitor of xanthine oxidase, is a metabolite of allopurinol.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Oxypurinol (DB05262)
- Weight
- Average: 152.1109
Monoisotopic: 152.033425392 - Chemical Formula
- C5H4N4O2
- Synonyms
- 1H-Pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione
- Alloxanthine
- DHPP
- Ossipurinolo
- Oxipurinol
- Oxipurinolum
- Oxoallopurinol
- Oxypurinol
- External IDs
- B. W. 55-5
- BW 55-5
- BW 555
- NSC-76239
Pharmacology
- Indication
Intended for the treatment of congestive heart failure and hyperuricemia.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Oxypurinol inhibits the enzyme xanthine oxidase, blocking the conversion of the oxypurines hypoxanthine and xanthine to uric acid. Elevated concentrations of oxypurine and oxypurine inhibition of xanthine oxidase through negative feedback results in a decrease in the concentrations of uric acid in the blood and urine. Oxypurinol also facilitates the incorporation of hypoxanthine and xanthine into DNA and RNA, resulting in further reductions of serum uric acid concentrations.
Target Actions Organism AXanthine dehydrogenase/oxidase inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
23.3 +/- 6.0 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAzathioprine The serum concentration of the active metabolites of Azathioprine can be increased when Azathioprine is used in combination with Oxypurinol. Didanosine The serum concentration of Didanosine can be increased when it is combined with Oxypurinol. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Imidazopyrimidines
- Sub Class
- Purines and purine derivatives
- Direct Parent
- Xanthines
- Alternative Parents
- Pyrazolo[3,4-d]pyrimidines / Alkaloids and derivatives / Pyrimidones / Vinylogous amides / Pyrazoles / Heteroaromatic compounds / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds show 3 more
- Substituents
- Alkaloid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Lactam / Organic nitrogen compound / Organic oxide / Organic oxygen compound show 10 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- pyrazolopyrimidine (CHEBI:28315) / C40 isoprenoids (tetraterpenes) (C07599)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- G97OZE5068
- CAS number
- 2465-59-0
- InChI Key
- HXNFUBHNUDHIGC-UHFFFAOYSA-N
- InChI
- InChI=1S/C5H4N4O2/c10-4-2-1-6-9-3(2)7-5(11)8-4/h1H,(H3,6,7,8,9,10,11)
- IUPAC Name
- 1H,2H,4H,5H,6H-pyrazolo[3,4-d]pyrimidine-4,6-dione
- SMILES
- O=C1NC2=C(C=NN2)C(=O)N1
References
- General References
- Iwanaga T, Kobayashi D, Hirayama M, Maeda T, Tamai I: Involvement of uric acid transporter in increased renal clearance of the xanthine oxidase inhibitor oxypurinol induced by a uricosuric agent, benzbromarone. Drug Metab Dispos. 2005 Dec;33(12):1791-5. Epub 2005 Aug 31. [Article]
- Baldus S, Koster R, Chumley P, Heitzer T, Rudolph V, Ostad MA, Warnholtz A, Staude HJ, Thuneke F, Koss K, Berger J, Meinertz T, Freeman BA, Munzel T: Oxypurinol improves coronary and peripheral endothelial function in patients with coronary artery disease. Free Radic Biol Med. 2005 Nov 1;39(9):1184-90. Epub 2005 Aug 10. [Article]
- Reyes AJ, Leary WP: Allopurinol or oxypurinol in heart failure therapy - a promising new development or end of story? Cardiovasc Drugs Ther. 2005 Oct;19(5):311-3. [Article]
- External Links
- Human Metabolome Database
- HMDB0000786
- KEGG Drug
- D02365
- KEGG Compound
- C07599
- PubChem Compound
- 4644
- PubChem Substance
- 175426963
- ChemSpider
- 4483
- BindingDB
- 50423777
- ChEBI
- 28315
- ChEMBL
- CHEMBL859
- ZINC
- ZINC000084462581
- PDBe Ligand
- 141
- Wikipedia
- Oxipurinol
- PDB Entries
- 1jrp / 3bdj / 8j79 / 8q6n
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data2, 3 Completed Treatment Congestive Heart Failure (CHF) 1 somestatus stop reason just information to hide 1 Completed Treatment Healthy Volunteers (HV) 1 somestatus stop reason just information to hide 1 Completed Treatment Sickle Cell Disease (SCD) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 4.58 mg/mL ALOGPS logP -0.65 ALOGPS logP -1.7 Chemaxon logS -1.5 ALOGPS pKa (Strongest Acidic) 6.25 Chemaxon pKa (Strongest Basic) 2.09 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 82.59 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 55.35 m3·mol-1 Chemaxon Polarizability 12.6 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9947 Caco-2 permeable - 0.6863 P-glycoprotein substrate Non-substrate 0.7699 P-glycoprotein inhibitor I Non-inhibitor 0.9233 P-glycoprotein inhibitor II Non-inhibitor 0.9933 Renal organic cation transporter Non-inhibitor 0.8992 CYP450 2C9 substrate Non-substrate 0.8677 CYP450 2D6 substrate Non-substrate 0.8245 CYP450 3A4 substrate Non-substrate 0.6962 CYP450 1A2 substrate Non-inhibitor 0.8123 CYP450 2C9 inhibitor Non-inhibitor 0.9289 CYP450 2D6 inhibitor Non-inhibitor 0.9104 CYP450 2C19 inhibitor Non-inhibitor 0.9251 CYP450 3A4 inhibitor Non-inhibitor 0.9142 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9919 Ames test Non AMES toxic 0.7265 Carcinogenicity Non-carcinogens 0.9002 Biodegradation Not ready biodegradable 0.8418 Rat acute toxicity 2.0587 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8389 hERG inhibition (predictor II) Non-inhibitor 0.9587
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 127.5443877 predictedDarkChem Lite v0.1.0 [M-H]- 135.2754758 predictedDarkChem Standard v0.1.0 [M-H]- 127.5468877 predictedDarkChem Lite v0.1.0 [M-H]- 127.5886877 predictedDarkChem Lite v0.1.0 [M-H]- 123.30826 predictedDeepCCS 1.0 (2019) [M-H]- 127.5443877 predictedDarkChem Lite v0.1.0 [M-H]- 135.2754758 predictedDarkChem Standard v0.1.0 [M-H]- 127.5468877 predictedDarkChem Lite v0.1.0 [M-H]- 127.5886877 predictedDarkChem Lite v0.1.0 [M-H]- 123.30826 predictedDeepCCS 1.0 (2019) [M+H]+ 127.7899877 predictedDarkChem Lite v0.1.0 [M+H]+ 138.478771 predictedDarkChem Standard v0.1.0 [M+H]+ 127.8237877 predictedDarkChem Lite v0.1.0 [M+H]+ 127.8309877 predictedDarkChem Lite v0.1.0 [M+H]+ 127.17339 predictedDeepCCS 1.0 (2019) [M+H]+ 127.7899877 predictedDarkChem Lite v0.1.0 [M+H]+ 138.478771 predictedDarkChem Standard v0.1.0 [M+H]+ 127.8237877 predictedDarkChem Lite v0.1.0 [M+H]+ 127.8309877 predictedDarkChem Lite v0.1.0 [M+H]+ 127.17339 predictedDeepCCS 1.0 (2019) [M+Na]+ 127.9563877 predictedDarkChem Lite v0.1.0 [M+Na]+ 127.8111877 predictedDarkChem Lite v0.1.0 [M+Na]+ 127.8819877 predictedDarkChem Lite v0.1.0 [M+Na]+ 127.8307877 predictedDarkChem Lite v0.1.0 [M+Na]+ 136.24437 predictedDeepCCS 1.0 (2019) [M+Na]+ 127.9563877 predictedDarkChem Lite v0.1.0 [M+Na]+ 127.8111877 predictedDarkChem Lite v0.1.0 [M+Na]+ 127.8819877 predictedDarkChem Lite v0.1.0 [M+Na]+ 127.8307877 predictedDarkChem Lite v0.1.0 [M+Na]+ 136.24437 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro)
- Specific Function
- 2 iron, 2 sulfur cluster binding
- Gene Name
- XDH
- Uniprot ID
- P47989
- Uniprot Name
- Xanthine dehydrogenase/oxidase
- Molecular Weight
- 146422.99 Da
References
- Iwanaga T, Kobayashi D, Hirayama M, Maeda T, Tamai I: Involvement of uric acid transporter in increased renal clearance of the xanthine oxidase inhibitor oxypurinol induced by a uricosuric agent, benzbromarone. Drug Metab Dispos. 2005 Dec;33(12):1791-5. Epub 2005 Aug 31. [Article]
- Baldus S, Koster R, Chumley P, Heitzer T, Rudolph V, Ostad MA, Warnholtz A, Staude HJ, Thuneke F, Koss K, Berger J, Meinertz T, Freeman BA, Munzel T: Oxypurinol improves coronary and peripheral endothelial function in patients with coronary artery disease. Free Radic Biol Med. 2005 Nov 1;39(9):1184-90. Epub 2005 Aug 10. [Article]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at November 18, 2007 18:22 / Updated at August 26, 2024 19:23