Oxypurinol

Identification

Name
Oxypurinol
Accession Number
DB05262
Description

Oxypurinol, an inhibitor of xanthine oxidase, is a metabolite of allopurinol.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
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.

Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
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.

TargetActionsOrganism
UXanthine dehydrogenase/oxidaseNot AvailableHumans
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
Learn about our commercial Adverse Effects data.
Learn More
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
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.
DrugInteraction
AzathioprineThe serum concentration of the active metabolites of Azathioprine can be increased when Azathioprine is used in combination with Oxypurinol.
DidanosineThe serum concentration of Didanosine can be increased when it is combined with Oxypurinol.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
Not Available

Products

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)

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
  1. 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. [PubMed:16135657]
  2. 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. [PubMed:16214034]
  3. 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. [PubMed:16382292]
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

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2, 3CompletedTreatmentCongestive Heart Failure (CHF)1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentSickle Cell Disease (SCD)1

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
PropertyValueSource
Water Solubility4.58 mg/mLALOGPS
logP-0.65ALOGPS
logP-1.7ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)6.25ChemAxon
pKa (Strongest Basic)2.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.59 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity55.35 m3·mol-1ChemAxon
Polarizability12.6 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9947
Caco-2 permeable-0.6863
P-glycoprotein substrateNon-substrate0.7699
P-glycoprotein inhibitor INon-inhibitor0.9233
P-glycoprotein inhibitor IINon-inhibitor0.9933
Renal organic cation transporterNon-inhibitor0.8992
CYP450 2C9 substrateNon-substrate0.8677
CYP450 2D6 substrateNon-substrate0.8245
CYP450 3A4 substrateNon-substrate0.6962
CYP450 1A2 substrateNon-inhibitor0.8123
CYP450 2C9 inhibitorNon-inhibitor0.9289
CYP450 2D6 inhibitorNon-inhibitor0.9104
CYP450 2C19 inhibitorNon-inhibitor0.9251
CYP450 3A4 inhibitorNon-inhibitor0.9142
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9919
Ames testNon AMES toxic0.7265
CarcinogenicityNon-carcinogens0.9002
BiodegradationNot ready biodegradable0.8418
Rat acute toxicity2.0587 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8389
hERG inhibition (predictor II)Non-inhibitor0.9587
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0w29-4900000000-2b2a5e7237cb7a9dd60e
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0ab9-9700000000-8017eefe2f766f6a3382
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0690-9100000000-b997025b96b7398143d2
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0f79-0900000000-3de88a143c5683886f8d
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , NegativeLC-MS/MSsplash10-0udi-0900000000-cbc9adb0643d1712be57
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0900000000-cbc9adb0643d1712be57
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0f79-0900000000-3de88a143c5683886f8d
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Xanthine oxidase activity
Specific 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. Ha...
Gene Name
XDH
Uniprot ID
P47989
Uniprot Name
Xanthine dehydrogenase/oxidase
Molecular Weight
146422.99 Da
References
  1. 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. [PubMed:16135657]
  2. 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. [PubMed:16214034]

Drug created on November 18, 2007 11:22 / Updated on June 12, 2020 10:52

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates