Allopurinol

Identification

Summary

Allopurinol is a xanthine oxidase inhibitor used to reduce urinary and serum uric acid concentrations in patients with gout, recurrent calcium oxalate calculi, and various malignancies.

Brand Names
Aloprim, Zyloprim
Generic Name
Allopurinol
DrugBank Accession Number
DB00437
Background

Gout is a disease that occurs by the deposition of monosodium urate crystals (MSU) in body tissues, especially around joints 7. This disease has been well-documented in historical medical records and appears in the biographies of several prominent, historically recognized individuals 7.

Allopurinol is a xanthine oxidase enzyme inhibitor that is considered to be one of the most effective drugs used to decrease urate levels and is frequently used in the treatment of chronic gout 6. It was initially approved by the FDA in 1966 12 and is now formulated by several manufacturers 13.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 136.1115
Monoisotopic: 136.03851077
Chemical Formula
C5H4N4O
Synonyms
  • 1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidin-4-one
  • 1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidine-4-one
  • 1H-Pyrazolo(3,4-d)pyrimidin-4-ol
  • 4-HPP
  • 4-Hydroxy-1H-pyrazolo(3,4-d)pyrimidine
  • 4-Hydroxy-3,4-pyrazolopyrimidine
  • 4-Hydroxypyrazolo(3,4-d)pyrimidine
  • 4-Hydroxypyrazolopyrimidine
  • 4-Hydroxypyrazolyl(3,4-d)pyrimidine
  • 4'-Hydroxypyrazolol(3,4-d)pyrimidine
  • 4H-Pyrazolo(3,4-d)pyrimidin-4-one
  • Allopurinol
  • Allopurinolum
  • Alopurinol
External IDs
  • BW 56-158
  • NSC-101655
  • NSC-1390

Pharmacology

Indication

Allopurinol is indicated in Label:

1) the management of patients with signs and symptoms of primary or secondary gout (acute attacks, tophi, joint destruction, uric acid lithiasis, and/or nephropathy).

2) the management of patients with leukemia, lymphoma and malignancies who are receiving cancer therapy which causes elevations of serum and urinary uric acid levels. Treatment with allopurinol should be discontinued when the potential for overproduction of uric acid is no longer present.

3) the management of patients with recurrent calcium oxalate calculi whose daily uric acid excretion exceeds 800 mg/day in male patients and 750 mg/day in female patients. Therapy in such patients should be carefully assessed initially and reassessed periodically to determine in each case that treatment is beneficial and that the benefits outweigh the risks.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatHyperuricemiaCombination Product in combination with: Benzbromarone (DB12319)••••••••••••••••••
Used in combination to treatHyperuricemiaCombination Product in combination with: Benzbromarone (DB12319)••••••••••••••••••
Used in combination to treatHyperuricemiaCombination Product in combination with: Benzbromarone (DB12319)••••••••••••••••••
Used in combination to treatHyperuricemiaCombination Product in combination with: Benzbromarone (DB12319)••••••••••••••••••
Used in combination to treatHyperuricemiaCombination Product in combination with: Benzbromarone (DB12319)••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Allopurinol decreases the production of uric acid by stopping the biochemical reactions that precede its formation Label. This process decreases urate and relieves the symptoms of gout, which may include painful tophi, joint pain, inflammation, redness, decreased range of motion, and swelling 2.

Mechanism of action

Allopurinol is a structural analog of the natural purine base, hypoxanthine. After ingestion, allopurinol is metabolized to its active metabolite, oxypurinol (alloxanthine) in the liver 11, which acts as an inhibitor of xanthine oxidase enzyme Label.

Allopurinol and its active metabolite inhibit xanthine oxidase, the enzyme that converts hypoxanthine to xanthine and xanthine to uric acid. Inhibition of this enzyme is responsible for the effects of allopurinol. This drug increases the reutilization of hypoxanthine and xanthine for nucleotide and nucleic acid synthesis by a process that involves the enzyme hypoxanthine-guanine phosphoribosyltransferase (HGPRTase). This process results in an increased nucleotide concentration, which causes feedback inhibition of de novo purine synthesis. The end result is decreased urine and serum uric acid concentrations 15, which decreases the incidence of gout symptoms.

Accompanying the reduction of serum uric acid by allopurinol is an increase in the serum and urine concentrations of hypoxanthine and xanthine (due to inhibition of xanthine oxidase). In the absence of allopurinol, regular urinary excretion of oxypurines almost entirely occurs in the form of uric acid. After the ingestion of allopurinol, the contents of excreted urine are hypoxanthine, xanthine, and uric acid. Because each substance has its own individual solubility, the concentration of uric acid in plasma is decreased without exposing the renal tissues to a high load of uric acid, thereby decreasing the risk of crystalluria. By lowering the uric acid concentration in the plasma below its limits of solubility, allopurinol encourages the dissolution of gout tophi. Although the levels of hypoxanthine and xanthine are found to be increased after allopurinol ingestion, the risk of deposition in renal tissues is less than that of uric acid, as they become more soluble and are rapidly excreted by the kidney 15.

TargetActionsOrganism
AXanthine dehydrogenase/oxidase
inhibitor
Humans
Absorption

This drug is about 90% absorbed from the gastrointestinal tract. Peak plasma levels normally occur at 1.5 hours and 4.5 hours post-dose for allopurinol and oxipurinol respectively. Following one oral dose of 300 mg of allopurinol, maximum plasma levels of about 3 mcg/mL of allopurinol and 6.5 mcg/mL of oxipurinol were measured Label.

Volume of distribution

Allopurinol and oxypurinol are both substrates for the enzyme xanthine oxidase, which is present in the cytoplasm of endothelial cells of capillaries, including sinusoids, with the highest activity demonstrated in the liver and intestinal lining. Tissue concentrations of allopurinol have not yet been reported in humans, however, it is probable that allopurinol and the metabolite oxypurinol would be measured in the highest concentrations in the abovementioned tissues. In animals, allopurinol concentrations are found to reach the highest levels in the blood, liver, intestine and heart, and lowest in the brain and lung tissues 9.

Protein binding

Allopurinol and oxypurinol are only negligibly bound to plasma proteins 10,9.

Metabolism

Allopurinol is rapidly metabolized to the corresponding xanthine analog, oxipurinol (alloxanthine), which is also an inhibitor of xanthine oxidase enzyme Label. Both allopurinol and oxypurinol inhibit the action of this enzyme. Allopurinol and oxypurinol are also converted by the purine salvage pathway to their respective ribonucleotides. The effect of these ribonucleotides related to the hypouricemic action of allopurinol in humans is not fully elucidated to this date. These metabolites may act to inhibit de novo purine biosynthesis by inhibiting the enzyme, amidophosphoribosyltransferase. The ribonucleotides have not been found to be incorporated in DNA 8.

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Route of elimination

Approximately 80% of orally ingested allopurinol is found excreted in the urine as various metabolites 9. About 20% of ingested allopurinol is excreted in the feces Label.

Half-life

The plasma half-life of allopurinol is 1-2 hours, due to its rapid renal clearance Label.

Clearance

Since allopurinol and its metabolites are mainly eliminated by the kidney, accumulation of this drug can occur in patients with renal dysfunction or failure, and the dose of allopurinol should, therefore, be reduced. With a creatinine clearance of 10 to 20 mL/min, a daily dosage of 200 mg of allopurinol is suitable. When the creatinine clearance is less than 10 mL/min, the daily dosage should not be higher than 100 mg. With severe renal impairment (creatinine clearance measured at less than 3 mL/min) a longer interval between doses may be required Label.

Adverse Effects
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Toxicity

Oral TDLO (rat): 10 mg/kg; Oral LD50 (mouse): 78 mg/kg; Oral TDLO (mouse): 100 mg/kg 14

Use in pregnancy

Reproductive studies have been completed using rats and rabbit models at doses up to twenty times the normal human dose ( about 5 mg/kg per day), and it was concluded that fertility was not impaired and there was no fetal harm. There is a published report of a study in pregnant mice administered 50 or 100 mg/kg allopurinol intraperitoneally on gestation days 10 or 13. There were increased numbers of dead fetuses in dams administered 100 mg/kg allopurinol, however, death did not occur in those given 50 mg/kg. There were higher numbers of external malformations in fetuses at both doses of allopurinol on gestation day 10 and higher numbers of skeletal malformations in fetuses at both doses on gestation day 13. Despite the above findings, there are no adequate or well-controlled studies in pregnant women. Because animal reproduction studies are not always predictive of human response, this drug should be used during pregnancy only if it is absolutely required Label.

Use in nursing

Both allopurinol and the metabolite oxipurinol have been found in the milk of a mother who was receiving allopurinol. Since the effect of allopurinol on the nursing infant is unknown, it is advisable to exercise caution when allopurinol is taken by a nursing woman Label.

Mutagenicity and carcinogenicity

Cytogenic studies demonstrate that allopurinol does not induce chromosomal abnormalities in human blood cells in vitro at concentrations up to 100 g/mL and in vivo at doses up to 60 mg/day for an average duration of 40 months. Allopurinol does not form nitroso compounds (which may be carcinogenic) or affect lymphocyte transformation in vitro. Evidence suggests that allopurinol does not have deleterious effects on DNA at any stage of the cell cycle and was not found to be mutagenic. No evidence of carcinogenicity has been observed in mice treated with allopurinol for up to a 2 year period 15.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
HLA class I histocompatibility antigen protein P5HLA-B*5801(G;G) / (G;T)G alleleADR Directly StudiedPatients who carry this allele are at a higher risk of experiencing severe cutaneous adverse reactions when treated with allopurinol.Details

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
AbacavirAllopurinol may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbemaciclibAbemaciclib may decrease the excretion rate of Allopurinol which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Allopurinol which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Allopurinol which could result in a higher serum level.
AcenocoumarolThe risk or severity of bleeding can be increased when Allopurinol is combined with Acenocoumarol.
Food Interactions
  • Avoid alcohol.
  • Take with a full glass of water.
  • Take with food.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Allopurinol sodium428673RC2Z17795-21-0PTJRZVJXXNYNLN-UHFFFAOYSA-M
Product Images
International/Other Brands
Adenock (Tanabe) / Allohexal / Alloril / Aluron / Milurit / Progout / Zyloric / Zyrik
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AlloprinTablet300 mgOralValeant Canada Lp Valeant Canada S.E.C.1980-12-312014-07-30Canada flag
AlloprinTablet200 mgOralValeant Canada Lp Valeant Canada S.E.C.1981-12-312014-07-30Canada flag
AlloprinTablet100 mgOralValeant Canada Lp Valeant Canada S.E.C.1979-12-312014-07-30Canada flag
AllopurinolTablet300 mg/1OralPreferreed Pharmaceuticals Inc.2012-06-04Not applicableUS flag
AllopurinolTablet100 mg/1OralA-S Medication Solutions2009-04-06Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ag-allopurinolTablet200 mgOralAngita Pharma Inc.2019-09-20Not applicableCanada flag
Ag-allopurinolTablet100 mgOralAngita Pharma Inc.2019-10-27Not applicableCanada flag
Ag-allopurinolTablet300 mgOralAngita Pharma Inc.2019-09-20Not applicableCanada flag
AllopurinolTablet300 mg/1OralPD-Rx Pharmaceuticals, Inc.2003-06-27Not applicableUS flag
AllopurinolTablet100 mg/1Oralbryant ranch prepack2003-06-27Not applicableUS flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
DUZALLOAllopurinol (200 MG) + Lesinurad (200 MG)Tablet, film coatedOralGrunenthal Gmbh2019-01-292020-08-28Italy flag
DuzalloAllopurinol (300 mg/1) + Lesinurad (200 mg/1)Tablet, film coatedOralIronwood Pharmaceuticals, Inc.2017-10-032019-11-30US flag
DUZALLOAllopurinol (300 MG) + Lesinurad (200 MG)Tablet, film coatedOralGrunenthal Gmbh2019-01-292020-08-28Italy flag
DUZALLOAllopurinol (200 MG) + Lesinurad (200 MG)Tablet, film coatedOralGrunenthal Gmbh2019-01-292020-08-28Italy flag
DuzalloAllopurinol (200 mg/1) + Lesinurad (200 mg/1)Tablet, film coatedOralIronwood Pharmaceuticals, Inc.2017-10-032020-04-30US flag

Categories

ATC Codes
M04AA01 — AllopurinolM04AA51 — Allopurinol, combinations
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyrazolo[3,4-d]pyrimidines. These are aromatic heterocyclic compounds containing a pyrazolo[3,4-d]pyrimidine ring system, which consists of a pyrazole ring fused to but and not sharing a nitrogen atom with a pyrimidine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrazolopyrimidines
Sub Class
Pyrazolo[3,4-d]pyrimidines
Direct Parent
Pyrazolo[3,4-d]pyrimidines
Alternative Parents
Pyrimidones / Vinylogous amides / Pyrazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
Substituents
Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organonitrogen compound / Organooxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heterobicyclic compound, nucleobase analogue (CHEBI:40279) / a small molecule (CPD-9024)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
63CZ7GJN5I
CAS number
315-30-0
InChI Key
OFCNXPDARWKPPY-UHFFFAOYSA-N
InChI
InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
IUPAC Name
1H-pyrazolo[3,4-d]pyrimidin-4-ol
SMILES
OC1=NC=NC2=C1C=NN2

References

Synthesis Reference

Druey, J. and Schmidt, P.; US. Patent 2868,803; January 13,1959; assigned to Ciba Pharmaceutical Products Inc. Hitchings, G.H. and Falco, EA.; U.S. Patent 3,474,098; October 21,1969; assigned to Bur- roughs Wellcome & Co. Cresswell, R.M.and Mentha, J.W.; US.Patent4,146,713; March27,1979; assigned to Bur- roughs Wellcome & Co.

General References
  1. Pacher P, Nivorozhkin A, Szabo C: Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev. 2006 Mar;58(1):87-114. [Article]
  2. Schlesinger N: Diagnosing and treating gout: a review to aid primary care physicians. Postgrad Med. 2010 Mar;122(2):157-61. doi: 10.3810/pgm.2010.03.2133. [Article]
  3. Suzuki I, Yamauchi T, Onuma M, Nozaki S: Allopurinol, an inhibitor of uric acid synthesis--can it be used for the treatment of metabolic syndrome and related disorders? Drugs Today (Barc). 2009 May;45(5):363-78. doi: 10.1358/dot.2009.45.5.1370460. [Article]
  4. Terkeltaub R: Update on gout: new therapeutic strategies and options. Nat Rev Rheumatol. 2010 Jan;6(1):30-8. doi: 10.1038/nrrheum.2009.236. [Article]
  5. George J, Struthers AD: Role of urate, xanthine oxidase and the effects of allopurinol in vascular oxidative stress. Vasc Health Risk Manag. 2009;5(1):265-72. Epub 2009 Apr 8. [Article]
  6. Seth R, Kydd AS, Buchbinder R, Bombardier C, Edwards CJ: Allopurinol for chronic gout. Cochrane Database Syst Rev. 2014 Oct 14;(10):CD006077. doi: 10.1002/14651858.CD006077.pub3. [Article]
  7. Ragab G, Elshahaly M, Bardin T: Gout: An old disease in new perspective - A review. J Adv Res. 2017 Sep;8(5):495-511. doi: 10.1016/j.jare.2017.04.008. Epub 2017 May 10. [Article]
  8. Murrell GA, Rapeport WG: Clinical pharmacokinetics of allopurinol. Clin Pharmacokinet. 1986 Sep-Oct;11(5):343-53. doi: 10.2165/00003088-198611050-00001. [Article]
  9. Reiter S, Simmonds HA, Webster DR, Watson AR: On the metabolism of allopurinol. Formation of allopurinol-1-riboside in purine nucleoside phosphorylase deficiency. Biochem Pharmacol. 1983 Jul 15;32(14):2167-74. [Article]
  10. Turnheim K, Krivanek P, Oberbauer R: Pharmacokinetics and pharmacodynamics of allopurinol in elderly and young subjects. Br J Clin Pharmacol. 1999 Oct;48(4):501-9. [Article]
  11. Ahmad Qurie; Rina Musa (2018). StatPearls: Allopurinol. StatPearls Publishing.
  12. Allopurinol approval package, FDA label [Link]
  13. Allopurinol, DailyMed [Link]
  14. Cayman Chem MSDS, Allopurinol [File]
  15. MedSafe NZ: Allopurinol [File]
Human Metabolome Database
HMDB0014581
KEGG Drug
D00224
PubChem Compound
2094
PubChem Substance
46508516
ChemSpider
2010
BindingDB
181133
RxNav
519
ChEBI
40279
ChEMBL
CHEMBL1467
ZINC
ZINC000013298313
Therapeutic Targets Database
DAP000773
PharmGKB
PA448320
PDBe Ligand
7HP
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Allopurinol
FDA label
Download (386 KB)
MSDS
Download (75.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceGout Chronic / Hyperuricemia1
4CompletedPreventionDiabetic Nephropathy / Type 1 Diabetes Mellitus1
4CompletedPreventionGout Flares / Impaired Renal Function1
4CompletedTreatmentAcute Coronary Syndrome (ACS)1
4CompletedTreatmentAdenine Phosphoribosyl Transferase Deficiency1

Pharmacoeconomics

Manufacturers
  • Apotex inc etobicoke site
  • Caraco pharmaceutical laboratories ltd
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Northstar healthcare holdings ltd
  • Par pharmaceutical inc
  • Purepac pharmaceutical co
  • Sandoz inc
  • Superpharm corp
  • Vintage pharmaceuticals inc
  • Watson laboratories inc
  • Abbott laboratories pharmaceutical products div
  • Dr reddys laboratories louisiana llc
  • Prometheus laboratories inc
  • Bedford laboratories
  • Bioniche pharma usa llc
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • A-S Medication Solutions LLC
  • Ascend Laboratories LLC
  • BASF Corp.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bioniche Pharma
  • Biotest Pharmaceuticals
  • Bryant Ranch Prepack
  • Caraco Pharmaceutical Labs
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Dept Health Central Pharmacy
  • DHHS Program Support Center Supply Service Center
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • DSM Corp.
  • H.J. Harkins Co. Inc.
  • Heartland Repack Services LLC
  • Kaiser Foundation Hospital
  • Liberty Pharmaceuticals
  • Major Pharmaceuticals
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mutual Pharmaceutical Co.
  • Mylan
  • Neighborcare Repackaging Inc.
  • Northstar Rx LLC
  • Nucare Pharmaceuticals Inc.
  • Paddock Labs
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pharmedix
  • Physicians Total Care Inc.
  • Piramal Healthcare
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Prometheus Laboratories Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • Spectrum Pharmaceuticals
  • UDL Laboratories
  • Va Cmop Dallas
  • Vangard Labs Inc.
  • Vintage Pharmaceuticals Inc.
  • Watson Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral300 mg
TabletOral
Injection, powder, lyophilized, for solutionIntravenous500 mg/25mL
TabletOral100.00 mg
TabletOral200 mg
Tablet, effervescent
GranuleOral4.4 %
Granule, effervescentOral300 mg
TabletOral150 MG
TabletOral10000000 mg
TabletOral100 MG
TabletOral300.00 mg
Tablet, film coatedOral
CapsuleOral
TabletOral
TabletOral300.000 mg
Tablet, film coatedOral
Tablet, soluble
TabletOral100 mg/1
TabletOral100.000 mg
TabletOral200 mg/1
TabletOral300 mg/1
GranuleOral300 MG
Tablet, coatedOral
Prices
Unit descriptionCostUnit
Aloprim 500 mg vial612.3USD vial
Allopurinol sodium 500 mg vial583.14USD vial
Allopurinol powder18.41USD g
Zyloprim 300 mg tablet1.89USD tablet
Zyloprim 100 mg tablet0.82USD tablet
Allopurinol 300 mg tablet0.46USD tablet
Allopurinol 100 mg tablet0.24USD tablet
Apo-Allopurinol 300 mg Tablet0.22USD tablet
Novo-Purol 300 mg Tablet0.22USD tablet
Apo-Allopurinol 200 mg Tablet0.14USD tablet
Novo-Purol 200 mg Tablet0.14USD tablet
Apo-Allopurinol 100 mg Tablet0.08USD tablet
Novo-Purol 100 mg Tablet0.08USD tablet
Suspendol-s liquid0.04USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8283369No2012-10-092028-11-26US flag
US8084483No2011-12-272029-08-17US flag
US8357713No2013-01-222028-11-26US flag
US8546437No2013-10-012029-04-29US flag
US9216179No2015-12-222030-08-02US flag
US8003681No2011-08-232025-08-25US flag
US8546436No2013-10-012032-02-29US flag
US9956205No2018-05-012031-12-28US flag
US10183012No2019-01-222028-11-26US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)>300 https://www.chemicalbook.com/ChemicalProductProperty_US_CB1181254.aspx
boiling point (°C)250.36https://www.chemicalbook.com/ChemicalProductProperty_US_CB1181254.aspx
water solubilitysolubility in water at 37°C is 80.0 mg/dL and is greater in an alkaline solutionFDA label
logP-1.8http://www.t3db.ca/toxins/T3D3477
logS-1.4http://www.t3db.ca/toxins/T3D3477
pKa10.2 (at 25℃)https://www.chemicalbook.com/ChemicalProductProperty_US_CB1181254.aspx
Predicted Properties
PropertyValueSource
Water Solubility22.0 mg/mLALOGPS
logP-0.41ALOGPS
logP0.031Chemaxon
logS-0.79ALOGPS
pKa (Strongest Acidic)8.47Chemaxon
pKa (Strongest Basic)1.25Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area74.69 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity34.98 m3·mol-1Chemaxon
Polarizability11.7 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.997
Blood Brain Barrier+0.9885
Caco-2 permeable-0.6232
P-glycoprotein substrateNon-substrate0.7409
P-glycoprotein inhibitor INon-inhibitor0.9135
P-glycoprotein inhibitor IINon-inhibitor0.9858
Renal organic cation transporterNon-inhibitor0.8653
CYP450 2C9 substrateNon-substrate0.8635
CYP450 2D6 substrateNon-substrate0.8256
CYP450 3A4 substrateNon-substrate0.6242
CYP450 1A2 substrateNon-inhibitor0.8817
CYP450 2C9 inhibitorNon-inhibitor0.9472
CYP450 2D6 inhibitorNon-inhibitor0.923
CYP450 2C19 inhibitorNon-inhibitor0.9198
CYP450 3A4 inhibitorNon-inhibitor0.858
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9169
Ames testNon AMES toxic0.7089
CarcinogenicityNon-carcinogens0.921
BiodegradationNot ready biodegradable0.9675
Rat acute toxicity2.1087 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9511
hERG inhibition (predictor II)Non-inhibitor0.9448
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.32 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0550-8900000000-225d53e43d6b82e006bf
Mass Spectrum (Electron Ionization)MSsplash10-000i-7900000000-f5a7601a354a9d25428f
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-4900000000-5d6d365d7525c7325e01
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000i-4900000000-ea448e075f973faea5ec
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-000l-8900000000-98d308813f954ccc66e0
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-9300000000-a0c962d1b7e8e76fd526
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-9100000000-d692c85314f5809e4758
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-01ox-9000000000-2662f35a8efe21c51958
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0900000000-4f38b316b66733e5ca8b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0900000000-547b3dac7e9b0d01ef66
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-0900000000-43ea9e7d5a0f94da482f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-000i-1900000000-fee6f9103fdd4cb1b6ed
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-01p9-1900000000-eb9ece2b9b724a6af483
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03dr-2900000000-85aef327ef1281780d05
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-788ea071a3463cfeb449
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0900000000-386b8a737e891fe218aa
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1900000000-b2af8ac33acc74bcd787
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0aou-9400000000-aa0dbe7b305164d7937d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uy1-9200000000-ad0f9bbce29a9c05d51d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kr-9700000000-74aa713f214db290843e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-121.513952
predicted
DarkChem Lite v0.1.0
[M-H]-121.416952
predicted
DarkChem Lite v0.1.0
[M-H]-122.79832
predicted
DeepCCS 1.0 (2019)
[M+H]+122.509652
predicted
DarkChem Lite v0.1.0
[M+H]+122.668152
predicted
DarkChem Lite v0.1.0
[M+H]+125.2091
predicted
DeepCCS 1.0 (2019)
[M+Na]+121.819352
predicted
DarkChem Lite v0.1.0
[M+Na]+122.118752
predicted
DarkChem Lite v0.1.0
[M+Na]+134.04073
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Suzuki I, Yamauchi T, Onuma M, Nozaki S: Allopurinol, an inhibitor of uric acid synthesis--can it be used for the treatment of metabolic syndrome and related disorders? Drugs Today (Barc). 2009 May;45(5):363-78. doi: 10.1358/dot.2009.45.5.1370460. [Article]
  3. Carro MD, Falkenstein E, Radke WJ, Klandorf H: Effects of allopurinol on uric acid concentrations, xanthine oxidoreductase activity and oxidative stress in broiler chickens. Comp Biochem Physiol C Toxicol Pharmacol. 2010 Jan;151(1):12-7. doi: 10.1016/j.cbpc.2009.07.010. Epub 2009 Aug 3. [Article]
  4. George J, Struthers AD: Role of urate, xanthine oxidase and the effects of allopurinol in vascular oxidative stress. Vasc Health Risk Manag. 2009;5(1):265-72. Epub 2009 Apr 8. [Article]
  5. Higgins P, Dawson J, Walters M: The potential for xanthine oxidase inhibition in the prevention and treatment of cardiovascular and cerebrovascular disease. Cardiovasc Psychiatry Neurol. 2009;2009:282059. doi: 10.1155/2009/282059. Epub 2009 Nov 4. [Article]
  6. Dincer HE, Dincer AP, Levinson DJ: Asymptomatic hyperuricemia: to treat or not to treat. Cleve Clin J Med. 2002 Aug;69(8):594, 597, 600-2 passim. [Article]
  7. Kelley WN, Wyngaarden JB: Effects of allopurinol and oxipurinol on purine synthesis in cultured human cells. J Clin Invest. 1970 Mar;49(3):602-9. [Article]
  8. Okamoto K: [Inhibitors of xanthine oxidoreductase]. Nihon Rinsho. 2008 Apr;66(4):748-53. [Article]
  9. Taha MO, Simoes MJ, Noguerol EC, Mendonca FP, Pascoalick HM, Alves RA, Vivian ME, Morales FP, Campos AC, Magalhaes KG, Venerando PS, Tersariol IL, Monteiro HP, Oliveira-Junior IS, Jurkiewicz A, Caricati-Neto A: Effects of allopurinol on ischemia and reperfusion in rabbit livers. Transplant Proc. 2009 Apr;41(3):820-3. doi: 10.1016/j.transproceed.2009.02.051. [Article]
  10. Terkeltaub R: Update on gout: new therapeutic strategies and options. Nat Rev Rheumatol. 2010 Jan;6(1):30-8. doi: 10.1038/nrrheum.2009.236. [Article]
  11. Pacher P, Nivorozhkin A, Szabo C: Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev. 2006 Mar;58(1):87-114. [Article]
  12. FDA label, Allopurinol [File]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xanthine dehydrogenase activity
Specific Function
Oxidase with broad substrate specificity, oxidizing aromatic azaheterocycles, such as N1-methylnicotinamide and N-methylphthalazinium, as well as aldehydes, such as benzaldehyde, retinal, pyridoxal...
Gene Name
AOX1
Uniprot ID
Q06278
Uniprot Name
Aldehyde oxidase
Molecular Weight
147916.735 Da
References
  1. Moriwaki Y, Yamamoto T, Nasako Y, Takahashi S, Suda M, Hiroishi K, Hada T, Higashino K: In vitro oxidation of pyrazinamide and allopurinol by rat liver aldehyde oxidase. Biochem Pharmacol. 1993 Sep 14;46(6):975-81. [Article]
  2. Yumiko Nasako, Tetsuya Yamamoto, Yuji Moriwaki, Sumio Takahashi, Zenta Tsutsumi, Toshikazu Hada, Kazuya Higashino (1995). Purine and Pyrimidine Metabolism in Man VIII. pringer Science+Business Media New York.
  3. BMJ Article: Allopurinol metabolism in a patient with xanthine oxidase deficiency [File]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. Pacher P, Nivorozhkin A, Szabo C: Therapeutic effects of xanthine oxidase inhibitors: renaissance half a century after the discovery of allopurinol. Pharmacol Rev. 2006 Mar;58(1):87-114. [Article]
  2. Seth R, Kydd AS, Buchbinder R, Bombardier C, Edwards CJ: Allopurinol for chronic gout. Cochrane Database Syst Rev. 2014 Oct 14;(10):CD006077. doi: 10.1002/14651858.CD006077.pub3. [Article]
  3. Murrell GA, Rapeport WG: Clinical pharmacokinetics of allopurinol. Clin Pharmacokinet. 1986 Sep-Oct;11(5):343-53. doi: 10.2165/00003088-198611050-00001. [Article]
  4. FDA label, Allopurinol [File]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Kobayashi Y, Ohshiro N, Tsuchiya A, Kohyama N, Ohbayashi M, Yamamoto T: Renal transport of organic compounds mediated by mouse organic anion transporter 3 (mOat3): further substrate specificity of mOat3. Drug Metab Dispos. 2004 May;32(5):479-83. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
Molecular Weight
60025.025 Da
References
  1. Kobayashi Y, Ohshiro N, Shibusawa A, Sasaki T, Tokuyama S, Sekine T, Endou H, Yamamoto T: Isolation, characterization and differential gene expression of multispecific organic anion transporter 2 in mice. Mol Pharmacol. 2002 Jul;62(1):7-14. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Nakamura M, Fujita K, Toyoda Y, Takada T, Hasegawa H, Ichida K: Investigation of the transport of xanthine dehydrogenase inhibitors by the urate transporter ABCG2. Drug Metab Pharmacokinet. 2018 Feb;33(1):77-81. doi: 10.1016/j.dmpk.2017.11.002. Epub 2017 Nov 22. [Article]
  2. Wen CC, Yee SW, Liang X, Hoffmann TJ, Kvale MN, Banda Y, Jorgenson E, Schaefer C, Risch N, Giacomini KM: Genome-wide association study identifies ABCG2 (BCRP) as an allopurinol transporter and a determinant of drug response. Clin Pharmacol Ther. 2015 May;97(5):518-25. doi: 10.1002/cpt.89. Epub 2015 Apr 6. [Article]
  3. Yu KH, Chang PY, Chang SC, Wu-Chou YH, Wu LA, Chen DP, Lo FS, Lu JJ: A comprehensive analysis of the association of common variants of ABCG2 with gout. Sci Rep. 2017 Aug 30;7(1):9988. doi: 10.1038/s41598-017-10196-2. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Liang Y, Li S, Chen L: The physiological role of drug transporters. Protein Cell. 2015 May;6(5):334-50. doi: 10.1007/s13238-015-0148-2. Epub 2015 Mar 24. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48