Identification
NameAllopurinol
Accession NumberDB00437  (APRD00435, DB03027)
TypeSmall Molecule
GroupsApproved
Description

A xanthine oxidase inhibitor that decreases uric acid production. It also acts as an antimetabolite on some simpler organisms.

Structure
Thumb
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
Allopurinolum
Alopurinol
External IDs BW 56-158 / NSC-101655 / NSC-1390
Product Ingredients
IngredientUNIICASInChI KeyDetails
Allopurinol Sodium428673RC2Z 17795-21-0PTJRZVJXXNYNLN-UHFFFAOYSA-MDetails
Product Images
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AlloprinTablet100 mgOralValeant Canada Lp Valeant Canada S.E.C.1979-12-312014-07-30Canada
AlloprinTablet200 mgOralValeant Canada Lp Valeant Canada S.E.C.1981-12-312014-07-30Canada
AlloprinTablet300 mgOralValeant Canada Lp Valeant Canada S.E.C.1980-12-312014-07-30Canada
AllopurinolTablet100 mg/1OralRed Pharm Drug, Inc.2009-04-06Not applicableUs
AllopurinolTablet300 mg/1OralRemedy Repack2013-01-112016-11-01Us
AllopurinolTablet100 mg/1OralAmerincan Health Packaging2009-03-11Not applicableUs
AllopurinolTablet300 mg/1Oralbryant ranch prepack2009-04-06Not applicableUs
AllopurinolTablet100 mg/1OralA S Medication Solutions2009-04-062017-06-20Us
AllopurinolTablet100 mg/1OralRemedy Repack2007-04-092016-11-30Us
AllopurinolTablet100 mg/1Oralbryant ranch prepack2009-04-06Not applicableUs
AllopurinolTablet300 mg/1OralRemedy Repack2010-01-13Not applicableUs
AllopurinolTablet100 mg/1Oralbryant ranch prepack2009-04-06Not applicableUs
AllopurinolTablet300 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
AllopurinolTablet300 mg/1OralPhysicians Total Care, Inc.1997-01-17Not applicableUs
AllopurinolTablet300 mg/1OralCardinal Health2009-03-11Not applicableUs
AllopurinolTablet300 mg/1OralRemedy Repack2017-04-17Not applicableUs
AllopurinolTablet100 mg/1OralRemedy Repack2017-05-25Not applicableUs
AllopurinolTablet100 mg/1OralRemedy Repack2009-09-15Not applicableUs
AllopurinolTablet300 mg/1OralAidarex Pharmaceuticals LLC2009-04-06Not applicableUs
AllopurinolTablet300 mg/1OralProficient Rx LP2009-04-06Not applicableUs
AllopurinolTablet100 mg/1OralActavis Pharma Company2009-04-06Not applicableUs
AllopurinolTablet300 mg/1Oralbryant ranch prepack2009-04-06Not applicableUs
AllopurinolTablet300 mgOralApotex Corporation1974-12-31Not applicableCanada
AllopurinolTablet100 mg/1OralState of Florida DOH Central Pharmacy2009-07-01Not applicableUs
AllopurinolTablet300 mg/1OralAmerincan Health Packaging2009-03-11Not applicableUs
AllopurinolTablet100 mg/1OralCardinal Health2009-03-11Not applicableUs
AllopurinolTablet300 mg/1OralPreferreed Pharmaceuticals Inc.2012-06-04Not applicableUs
AllopurinolTablet100 mg/1OralAidarex Pharmaceuticals LLC2009-04-06Not applicableUs
AllopurinolTablet300 mg/1OralPd Rx Pharmaceuticals, Inc.2009-04-06Not applicableUs
AllopurinolTablet300 mg/1OralA S Medication Solutions2009-04-062017-02-16Us
AllopurinolTablet100 mg/1OralAidarex Pharmaceuticals LLC2009-04-06Not applicableUs
AllopurinolTablet100 mg/1OralProficient Rx LP2009-04-06Not applicableUs
AllopurinolTablet300 mg/1OralActavis Pharma Company2009-04-06Not applicableUs
AllopurinolTablet100 mg/1OralPhysicians Total Care, Inc.2002-05-10Not applicableUs
Allopurinol Tablets 100mgTablet100 mgOralLaboratoires Confab IncNot applicableNot applicableCanada
Allopurinol Tablets 200mgTablet200 mgOralLaboratoires Confab IncNot applicableNot applicableCanada
Allopurinol Tablets 300mgTablet300 mgOralLaboratoires Confab IncNot applicableNot applicableCanada
Allopurinol-100Tablet100 mgOralPro Doc Limitee1982-12-31Not applicableCanada
Allopurinol-200Tablet200 mgOralPro Doc Limitee1995-12-31Not applicableCanada
Allopurinol-300Tablet300 mgOralPro Doc Limitee1982-12-31Not applicableCanada
AloprimInjection, powder, lyophilized, for solution500 mg/25mLIntravenousMylan Institutional1996-05-01Not applicableUs
Ipg-allopurinolTablet100 mgOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Ipg-allopurinolTablet200 mgOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Ipg-allopurinolTablet300 mgOralMarcan Pharmaceuticals IncNot applicableNot applicableCanada
Jamp-allopurinolTablet200 mgOralJamp Pharma Corporation2014-03-10Not applicableCanada
Jamp-allopurinolTablet100 mgOralJamp Pharma Corporation2014-03-10Not applicableCanada
Jamp-allopurinolTablet300 mgOralJamp Pharma Corporation2014-03-10Not applicableCanada
Mar-allopurinolTablet100 mgOralMarcan Pharmaceuticals Inc2013-04-17Not applicableCanada
Mar-allopurinolTablet200 mgOralMarcan Pharmaceuticals Inc2013-04-17Not applicableCanada
Mar-allopurinolTablet300 mgOralMarcan Pharmaceuticals Inc2013-04-17Not applicableCanada
Novo-purol Tab 100mgTablet100 mgOralNovopharm Limited1981-12-312015-10-26Canada
Novo-purol Tab 200 mgTablet200 mgOralNovopharm Limited1982-12-312015-10-26Canada
Novo-purol Tab 300mgTablet300 mgOralNovopharm Limited1981-12-312015-10-26Canada
Ntp-allopurinolTablet300 mgOralTevaNot applicableNot applicableCanada
Ntp-allopurinolTablet200 mgOralTevaNot applicableNot applicableCanada
Ntp-allopurinolTablet100 mgOralTevaNot applicableNot applicableCanada
Nu-allopurinolTablet300 mgOralNu Pharm IncNot applicableNot applicableCanada
Nu-allopurinolTablet100 mgOralNu Pharm IncNot applicableNot applicableCanada
Nu-allopurinolTablet200 mgOralNu Pharm IncNot applicableNot applicableCanada
Purinol Tab 100mgTablet100 mgOralCarter Horner Corp.1978-12-312001-01-02Canada
Purinol Tab 200mgTablet200 mgOralCarter Horner Corp.1978-12-312001-01-02Canada
Purinol Tab 300mgTablet300 mgOralCarter Horner Corp.1978-12-312001-01-02Canada
Riva-purinol 100mg TabletsTablet100 mgOralLaboratoire Riva Inc1999-10-152003-07-28Canada
Riva-purinol 200mg TabletsTablet200 mgOralLaboratoire Riva Inc1999-10-152003-07-28Canada
Riva-purinol 300mg TabletsTablet300 mgOralLaboratoire Riva Inc1999-10-152003-07-28Canada
ZyloprimTablet200 mgOralAa Pharma Inc1981-12-31Not applicableCanada
ZyloprimTablet100 mg/1OralRemedy Repack2017-05-25Not applicableUs
ZyloprimTablet300 mg/1OralRemedy Repack2016-11-17Not applicableUs
ZyloprimTablet100 mgOralAa Pharma Inc1981-12-31Not applicableCanada
ZyloprimTablet100 mg/1OralSebela Pharmaceuticals Inc.2017-05-23Not applicableUs
ZyloprimTablet100 mg/1OralPrometheus Laboratories1966-08-19Not applicableUs
ZyloprimTablet300 mgOralAa Pharma Inc1981-12-31Not applicableCanada
ZyloprimTablet300 mg/1OralPrometheus Laboratories1966-08-19Not applicableUs
ZyloprimTablet300 mg/1OralSebela Pharmaceuticals Inc.2017-05-23Not applicableUs
Zyloprim 100Tablet100 mgOralGlaxosmithkline Inc1966-12-312006-11-21Canada
Zyloprim 200Tablet200 mgOralGlaxosmithkline Inc1980-12-312007-04-04Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AllopurinolTablet100 mg/1OralBlenheim Pharmacal, Inc.2013-10-07Not applicableUs
AllopurinolTablet300 mg/1OralClinical Solutions Wholsesale2003-06-272017-06-20Us
AllopurinolTablet100 mg/1OralA S Medication Solutions2003-06-272017-06-20Us
AllopurinolTablet100 mg/1OralPreferreed Pharmaceuticals Inc.2016-09-13Not applicableUs
AllopurinolTablet100 mg/1OralUnit Dose Services2003-06-27Not applicableUs
AllopurinolTablet300 mg/1OralNorthwind Pharmaceuticals2015-02-04Not applicableUs
AllopurinolTablet300 mg/1OralRemedy Repack2015-09-02Not applicableUs
AllopurinolTablet100 mg/1OralDr Reddy's Laboratories2009-10-01Not applicableUs
AllopurinolTablet300 mg/1OralPreferreed Pharmaceuticals Inc.2009-10-01Not applicableUs
AllopurinolTablet100 mg/1OralState of Florida DOH Central Pharmacy2014-01-01Not applicableUs63304 0539 10 nlmimage10 db396dab
AllopurinolTablet300 mg/1OralRemedy Repack2015-03-092017-03-14Us
AllopurinolTablet100 mg/1OralMylan Pharmaceuticals1986-10-24Not applicableUs
AllopurinolTablet300 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs1986-10-24Not applicableUs
AllopurinolTablet300 mg/1OralNorth Star Rx Llc2009-11-16Not applicableUs16714 0042 11 nlmimage10 3f441f90
AllopurinolTablet100 mg/1OralPreferreed Pharmaceuticals Inc.2012-06-04Not applicableUs
AllopurinolTablet100 mg/1OralGolden State Medical Supply2015-02-09Not applicableUs
AllopurinolTablet300 mg/1OralCardinal Health2011-05-20Not applicableUs
AllopurinolTablet300 mg/1OralMc Kesson2009-11-16Not applicableUs
AllopurinolTablet300 mg/1OralA S Medication Solutions2003-06-272017-06-20Us
AllopurinolTablet300 mg/1OralAphena Pharma Solutions Tennessee, Inc.2003-06-27Not applicableUs
AllopurinolTablet300 mg/1OralQualitest2003-06-27Not applicableUs
AllopurinolTablet100 mg/1OralMylan Institutional1997-04-29Not applicableUs
AllopurinolTablet100 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2003-06-27Not applicableUs
AllopurinolTablet100 mg/1OralAv Pak2016-08-01Not applicableUs
AllopurinolTablet300 mg/1OralSt. Marys Medical Park Pharmacy2014-02-20Not applicableUs
AllopurinolTablet100 mg/1OralNcs Health Care Of Ky, Inc Dba Vangard Labs1986-10-24Not applicableUs
AllopurinolTablet100 mg/1OralNorth Star Rx Llc2009-11-16Not applicableUs16714 0041 12 nlmimage10 23441180
AllopurinolTablet300 mg/1OralPreferreed Pharmaceuticals Inc.2014-10-20Not applicableUs
AllopurinolTablet300 mg/1OralA S Medication Solutions2009-11-162017-06-20Us
AllopurinolTablet100 mg/1OralAphena Pharma Solutions Tennessee, Inc.1986-10-24Not applicableUs
AllopurinolTablet100 mg/1OralNucare Pharmaceuticals, Inc.2015-04-29Not applicableUs
AllopurinolTablet300 mg/1OralRemedy Repack2013-05-142017-01-18Us63304 0540 05 nlmimage10 c739638b
AllopurinolTablet100 mg/1OralRemedy Repack2017-05-02Not applicableUs
AllopurinolTablet300 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2013-05-14Not applicableUs
AllopurinolTablet100 mg/1OralMutual Pharmaceutical1987-01-09Not applicableUs
AllopurinolTablet100 mg/1OralIpca Laboratories Limited2011-06-06Not applicableUs
AllopurinolTablet, coated100 mg/1OralMajor2011-12-01Not applicableUs
AllopurinolTablet300 mg/1OralPd Rx Pharmaceuticals, Inc.2003-06-27Not applicableUs
AllopurinolTablet100 mg/1OralRemedy Repack2010-12-022016-10-13Us
AllopurinolTablet300 mg/1OralIngenus Pharmaceuticals Llc2016-08-08Not applicableUs
AllopurinolTablet300 mg/1OralAphena Pharma Solutions Tennessee, Inc.2015-02-09Not applicableUs
AllopurinolTablet300 mg/1OralGolden State Medical Supply2015-02-09Not applicableUs
AllopurinolTablet100 mg/1OralUnit Dose Services2009-10-01Not applicableUs
AllopurinolTablet300 mg/1OralBlenheim Pharmacal, Inc.2013-10-07Not applicableUs
AllopurinolTablet300 mg/1OralRemedy Repack2015-01-23Not applicableUs00603 2116 28 nlmimage10 a23fd13e
AllopurinolTablet100 mg/1OralA S Medication Solutions2009-11-162017-06-20Us
AllopurinolTablet300 mg/1OralPreferreed Pharmaceuticals Inc.2016-10-17Not applicableUs
AllopurinolTablet300 mg/1OralUnit Dose Services2003-06-27Not applicableUs
AllopurinolTablet300 mg/1OralRemedy Repack2013-02-212016-12-22Us
AllopurinolTablet300 mg/1OralAvera Mc Kennan Hospital2016-10-24Not applicableUs
AllopurinolTablet300 mg/1OralDr Reddy's Laboratories2009-10-01Not applicableUs
AllopurinolTablet100 mg/1OralPreferreed Pharmaceuticals Inc.2009-10-01Not applicableUs
AllopurinolTablet300 mg/1OralState of Florida DOH Central Pharmacy2014-10-01Not applicableUs
AllopurinolTablet100 mg/1OralRanbaxy Inc.2011-06-06Not applicableUs
AllopurinolTablet300 mg/1OralMylan Pharmaceuticals1986-10-24Not applicableUs
AllopurinolTablet100 mg/1OralAccord Healthcare Limited2015-04-29Not applicableUs
AllopurinolTablet300 mg/1OralRebel Distributors2009-06-01Not applicableUs
AllopurinolTablet100 mg/1OralCardinal Health2011-05-20Not applicableUs
AllopurinolTablet100 mg/1OralAphena Pharma Solutions Tennessee, Inc.2003-06-27Not applicableUs
AllopurinolTablet100 mg/1OralMajor1998-08-03Not applicableUs
AllopurinolTablet300 mg/1OralMylan Institutional1997-04-29Not applicableUs
AllopurinolTablet100 mg/1OralStat Rx USA2003-06-27Not applicableUs
AllopurinolTablet300 mg/1OralAv Pak2016-08-01Not applicableUs
AllopurinolTablet100 mg/1OralMajor Pharamceuticals2003-06-27Not applicableUs
AllopurinolTablet100 mg/1OralRemedy Repack2013-05-222017-01-10Us
AllopurinolTablet100 mg/1OralUnit Dose Services1987-01-09Not applicableUs
AllopurinolTablet100 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2010-04-01Not applicableUs
AllopurinolTablet300 mg/1OralPreferreed Pharmaceuticals Inc.2016-06-14Not applicableUs
AllopurinolTablet100 mg/1OralRemedy Repack2017-01-31Not applicableUs
AllopurinolTablet300 mg/1OralMutual Pharmaceutical1987-01-09Not applicableUs
AllopurinolTablet300 mg/1OralIpca Laboratories Limited2011-06-06Not applicableUs
AllopurinolTablet, coated300 mg/1OralMajor2011-12-01Not applicableUs
AllopurinolTablet100 mg/1OralClinical Solutions Wholsesale2003-06-272017-06-20Us
AllopurinolTablet100 mg/1OralQualitest2003-06-27Not applicableUs
AllopurinolTablet300 mg/1OralAccord Healthcare Limited2015-04-29Not applicableUs
AllopurinolTablet100 mg/1OralRebel Distributors2009-06-01Not applicableUs
AllopurinolTablet300 mg/1OralAphena Pharma Solutions Tennessee, Inc.1986-10-24Not applicableUs
AllopurinolTablet100 mg/1OralSt. Marys Medical Park Pharmacy2013-04-25Not applicableUs
AllopurinolTablet300 mg/1OralUnit Dose Services2003-06-27Not applicableUs
AllopurinolTablet300 mg/1OralBlenheim Pharmacal, Inc.2015-04-21Not applicableUs
AllopurinolTablet100 mg/1OralRemedy Repack2015-04-022017-04-14Us
AllopurinolTablet300 mg/1OralA S Medication Solutions2003-06-272017-06-20Us
AllopurinolTablet300 mg/1OralNucare Pharmaceuticals, Inc.2015-04-29Not applicableUs
AllopurinolTablet100 mg/1OralRemedy Repack2013-05-132017-01-19Us
AllopurinolTablet100 mg/1OralRemedy Repack2017-04-21Not applicableUs
AllopurinolTablet100 mg/1OralCardinal Health1987-01-09Not applicableUs
AllopurinolTablet100 mg/1OralMc Kesson2009-11-16Not applicableUs
AllopurinolTablet100 mg/1OralA S Medication Solutions2003-06-272017-06-20Us
AllopurinolTablet300 mg/1OralRanbaxy Inc.2011-06-06Not applicableUs
AllopurinolTablet300 mg/1OralMajor Pharamceuticals2003-06-27Not applicableUs
AllopurinolTablet100 mg/1OralRemedy Repack2013-05-232017-01-07Us
AllopurinolTablet100 mg/1OralRed Pharm Drug, Inc.2003-06-27Not applicableUs
AllopurinolTablet300 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2003-06-27Not applicableUs
AllopurinolTablet100 mg/1OralMc Kesson Contract Packaging2011-12-16Not applicableUs
AllopurinolTablet300 mg/1OralMajor2004-12-10Not applicableUs
AllopurinolTablet100 mg/1OralRemedy Repack2012-09-282017-01-11Us
AllopurinolTablet100 mg/1OralPd Rx Pharmaceuticals, Inc.2003-06-27Not applicableUs
AllopurinolTablet100 mg/1OralIngenus Pharmaceuticals Llc2016-08-08Not applicableUs
Allopurinol SodiumInjection, powder, lyophilized, for solution500 mg/25mLIntravenousWest Ward Pharmaceutical2004-09-01Not applicableUs
Apo-allopurinolTablet300 mgOralApotex Corporation2013-04-23Not applicableCanada
Apo-allopurinolTablet100 mgOralApotex Corporation2013-04-23Not applicableCanada
Apo-allopurinolTablet200 mgOralApotex Corporation2013-04-23Not applicableCanada
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AdenockTanabe
AllohexalNot Available
AllorilNot Available
AluronNot Available
MiluritNot Available
ProgoutNot Available
ZyloricNot Available
ZyrikNot Available
Brand mixturesNot Available
Categories
UNII63CZ7GJN5I
CAS number315-30-0
WeightAverage: 136.1115
Monoisotopic: 136.03851077
Chemical FormulaC5H4N4O
InChI KeyOFCNXPDARWKPPY-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,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one
SMILES
O=C1N=CN=C2NNC=C12
Pharmacology
Indication

For the treatment of hyperuricemia associated with primary or secondary gout. Also indicated for the treatment of primary or secondary uric acid nephropathy, with or without the symptoms of gout, as well as chemotherapy-induced hyperuricemia and recurrent renal calculi.

Structured Indications
Pharmacodynamics

Allopurinol, a structural analog of the natural purine base hypoxanthine, is used to prevent gout and renal calculi due to either uric acid or calcium oxalate and to treat uric acid nephropathy, hyperuricemia, and some solid tumors.

Mechanism of action

Allopurinol and its active metabolite, 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 serum and urine. Allopurinol also facilitates the incorporation of hypoxanthine and xanthine into DNA and RNA, leading to a feedback inhibition of de novo purin synthesis and a decrease in serum uric acid concentrations as a result of an increase in nucleotide concentration.

TargetKindPharmacological actionActionsOrganismUniProt ID
Xanthine dehydrogenase/oxidaseProteinyes
inhibitor
HumanP47989 details
Related Articles
Absorption

Approximately 80-90% absorbed from the gastrointestinal tract.

Volume of distributionNot Available
Protein binding

Allopurinol and oxypurinol are not bound to plasma proteins

Metabolism

Hepatic

SubstrateEnzymesProduct
Allopurinol
oxypurinolDetails
Route of elimination

Approximately 20% of the ingested allopurinol is excreted in the feces.

Half life

1-3 hours

ClearanceNot Available
Toxicity

LD50=214 mg/kg (in mice)

Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
HLA class I histocompatibility antigen protein P5HLA-B*5701(G;G) / (G;T)G allele ADR Directly StudiedSevere cutaneous adverse reaction Details
Interactions
Drug Interactions
DrugInteractionDrug group
AcenocoumarolAllopurinol may increase the anticoagulant activities of Acenocoumarol.Approved
Aluminum hydroxideAluminum hydroxide can cause a decrease in the absorption of Allopurinol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Ambroxol acefyllinateThe serum concentration of Ambroxol acefyllinate can be increased when it is combined with Allopurinol.Experimental
AminophyllineThe serum concentration of Aminophylline can be increased when it is combined with Allopurinol.Approved
AmoxicillinThe risk of a hypersensitivity reaction to Amoxicillin is increased when it is combined with Allopurinol.Approved, Vet Approved
AmpicillinThe risk of a hypersensitivity reaction to Ampicillin is increased when it is combined with Allopurinol.Approved, Vet Approved
AzathioprineThe serum concentration of the active metabolites of Azathioprine can be increased when Azathioprine is used in combination with Allopurinol.Approved
BenazeprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Benazepril.Approved, Investigational
BendamustineThe risk or severity of adverse effects can be increased when Allopurinol is combined with Bendamustine.Approved, Investigational
BendroflumethiazideThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Bendroflumethiazide.Approved
Bismuth SubcitrateBismuth Subcitrate can cause a decrease in the absorption of Allopurinol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
BumetanideThe risk or severity of adverse effects can be increased when Bumetanide is combined with Allopurinol.Approved
Calcium CarbonateCalcium carbonate can cause a decrease in the absorption of Allopurinol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
CandoxatrilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Candoxatril.Experimental
CaptoprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Captopril.Approved
CarbamazepineThe serum concentration of Carbamazepine can be increased when it is combined with Allopurinol.Approved, Investigational
ChlorothiazideThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Chlorothiazide.Approved, Vet Approved
ChlorpropamideThe serum concentration of Chlorpropamide can be increased when it is combined with Allopurinol.Approved
ChlorthalidoneThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Chlorthalidone.Approved
CilazaprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Cilazapril.Approved
CyclophosphamideThe risk or severity of adverse effects can be increased when Allopurinol is combined with Cyclophosphamide.Approved, Investigational
DicoumarolAllopurinol may increase the anticoagulant activities of Dicoumarol.Approved
DidanosineThe serum concentration of Didanosine can be increased when it is combined with Allopurinol.Approved
DoxofyllineThe serum concentration of Doxofylline can be increased when it is combined with Allopurinol.Approved
DyphyllineThe serum concentration of Dyphylline can be increased when it is combined with Allopurinol.Approved
EnalaprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Enalapril.Approved, Vet Approved
EnalaprilatThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Enalaprilat.Approved
Etacrynic acidThe risk or severity of adverse effects can be increased when Etacrynic acid is combined with Allopurinol.Approved
Ethyl biscoumacetateAllopurinol may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindioneAllopurinol may increase the anticoagulant activities of Fluindione.Investigational
FosinoprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Fosinopril.Approved
FurosemideThe risk or severity of adverse effects can be increased when Furosemide is combined with Allopurinol.Approved, Vet Approved
HydrochlorothiazideThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazideThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Hydroflumethiazide.Approved
ImidaprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Imidapril.Investigational
IndapamideThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Indapamide.Approved
LisinoprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Lisinopril.Approved, Investigational
MagaldrateMagaldrate can cause a decrease in the absorption of Allopurinol resulting in a reduced serum concentration and potentially a decrease in efficacy.Withdrawn
Magnesium carbonateMagnesium carbonate can cause a decrease in the absorption of Allopurinol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium HydroxideMagnesium hydroxide can cause a decrease in the absorption of Allopurinol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium oxideMagnesium oxide can cause a decrease in the absorption of Allopurinol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
Magnesium TrisilicateMagnesium Trisilicate can cause a decrease in the absorption of Allopurinol resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
MercaptopurineThe serum concentration of Mercaptopurine can be increased when it is combined with Allopurinol.Approved
MethyclothiazideThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Methyclothiazide.Approved
MetolazoneThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Metolazone.Approved
MoexiprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Moexipril.Approved
OmapatrilatThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Omapatrilat.Investigational
PegloticaseThe risk or severity of adverse effects can be increased when Allopurinol is combined with Pegloticase.Approved
PerindoprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Perindopril.Approved
PhenindioneAllopurinol may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonAllopurinol may increase the anticoagulant activities of Phenprocoumon.Approved
PiretanideThe risk or severity of adverse effects can be increased when Piretanide is combined with Allopurinol.Experimental
PolythiazideThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Polythiazide.Approved
QuinaprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Quinapril.Approved, Investigational
QuinethazoneThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Quinethazone.Approved
RamiprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Ramipril.Approved
RescinnamineThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Rescinnamine.Approved
SpiraprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Spirapril.Approved
TegafurThe therapeutic efficacy of Tegafur can be decreased when used in combination with Allopurinol.Approved
TemocaprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Temocapril.Experimental, Investigational
TheophyllineThe serum concentration of Theophylline can be increased when it is combined with Allopurinol.Approved
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Allopurinol.Approved
TrandolaprilThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Trandolapril.Approved
TrichlormethiazideThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Trichlormethiazide.Approved, Vet Approved
WarfarinAllopurinol may increase the anticoagulant activities of Warfarin.Approved
Food Interactions
  • Avoid alcohol.
  • Take with a full glass of water.
  • Take with food.
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. [PubMed:16507884 ]
  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. [PubMed:20203467 ]
  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. [PubMed:19584965 ]
  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. [PubMed:20046204 ]
  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. [PubMed:19436671 ]
External Links
ATC CodesM04AA01 — AllopurinolM04AA51 — Allopurinol, combinations
AHFS Codes
  • 92:00.00
PDB Entries
FDA labelNot Available
MSDSDownload (75.9 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingBasic ScienceHyperuricemia1
1CompletedBasic ScienceGout Acute1
1CompletedTreatmentFasting State1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentInflammatory Bowel Diseases (IBD)1
1CompletedTreatmentLeukemias / Malignant Lymphomas / Multiple Myeloma (MM) / Myelodysplastic Syndromes / Plasma Cell Neoplasms1
1CompletedTreatmentTuberculosis1
1RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL)1
1, 2CompletedTreatmentAcute Undifferentiated Leukemia (AUL) / B-cell Adult Acute Lymphoblastic Leukemia / B-cell Childhood Acute Lymphoblastic Leukemia / L1 Adult Acute Lymphoblastic Leukemia / L1 Childhood Acute Lymphoblastic Leukemia / L2 Adult Acute Lymphoblastic Leukemia / L2 Childhood Acute Lymphoblastic Leukemia / Philadelphia Chromosome Negative Adult Precursor Acute Lymphoblastic Leukemia / Philadelphia Chromosome Positive Adult Precursor Acute Lymphoblastic Leukemia / Philadelphia Chromosome Positive Childhood Precursor Acute Lymphoblastic Leukemia / T-cell Adult Acute Lymphoblastic Leukemia / T-cell Childhood Acute Lymphoblastic Leukemia / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
1, 2TerminatedTreatmentHypertensive / Transplant, Kidney1
1, 2WithdrawnBasic ScienceCardiovascular Disease (CVD) / Congestive Cardiomyopathy / Congestive Heart Failure (CHF) / Heart Diseases1
2Active Not RecruitingTreatmentChronic Lymphocytic Leukaemia (CLL)1
2CompletedPreventionGout Acute1
2CompletedPreventionHand-foot Syndrome1
2CompletedPreventionHepatic Enzymes / Metabolic Syndrome Parameters / Systolic and Diastolic Blood Pressure Levels / Uric Acid Levels1
2CompletedPreventionMetabolic Syndromes1
2CompletedTreatmentCongestive Heart Failure (CHF)1
2CompletedTreatmentElevated Serum Uric Acid / Heart Failure, Unspecified1
2CompletedTreatmentGout Acute5
2CompletedTreatmentGout Acute / Hyperuricemia1
2CompletedTreatmentGout and Hyperuricemia1
2CompletedTreatmentHypertension,Essential1
2CompletedTreatmentHypertensive / Severe Obstructive Sleep Apnea (Apnea Hypopnea Index > 30 Events/Hour)1
2CompletedTreatmentHyperuricemia / Moderate to Severe Gout1
2CompletedTreatmentHyperuricosuria / Renal Stones1
2CompletedTreatmentLeishmaniasis1
2CompletedTreatmentLeukemias2
2CompletedTreatmentLeukemias / Malignant Lymphomas2
2CompletedTreatmentLeukemias / Malignant Lymphomas / Multiple Myeloma (MM) / Myelodysplastic Syndromes / Myeloproliferative Neoplasms / Plasma Cell Neoplasms1
2Not Yet RecruitingTreatmentChronic Lymphocytic Leukaemia (CLL) / Primary Lymphoid Haematopoietic Neoplasms / Small Lymphocytic Lymphoma (SLL)1
2RecruitingTreatmentAcute Lymphocytic Leukemia (ALL) / Acute Myelogenous Leukaemia (AML) / Burkitt's Lymphoma / Chronic Lymphocytic Leukaemia (CLL) / Chronic Myelogenous Leukemia (CML) / Follicular Lymphoma (FL) / Hematological Diseases / Leukemia, Plasma Cell / Leukemia, Prolymphocytic / Lymphoma, B-Cell / Lymphoma, Lymphoblastic / Lymphoma, Mantle-Cell / Lymphoplasmacytic Lymphoma / Multiple Myeloma (MM) / Myelodysplastic Syndromes / Myeloproliferative Syndromes / Non-Hodgkin's Lymphoma (NHL) / Small Lymphocytic Lymphoma (SLL)1
2RecruitingTreatmentChronic Lymphocytic Leukaemia (CLL) / Leukemias1
2RecruitingTreatmentLymphoblastic Leukemia, Acute, Childhood1
2TerminatedTreatmentAcute Myelogenous Leukaemia (AML) / Refractory Acute Myelogenous Leukemia1
2TerminatedTreatmentAdult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(15;17)(q22;q12) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Blastic Phase Chronic Myelogenous Leukemia / Contiguous Stage II Adult Burkitt Lymphoma / De Novo Myelodysplastic Syndromes / Noncontiguous Stage II Adult Burkitt Lymphoma / Previously Treated Myelodysplastic Syndromes / Recurrent Adult Acute Lymphoblastic Leukemia / Recurrent Adult Acute Myeloid Leukemia / Recurrent Adult Burkitt Lymphoma / Stage I Adult Burkitt Lymphoma / Stage III Adult Burkitt Lymphoma / Stage IV Adult Burkitt Lymphoma / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Adult Acute Myeloid Leukemia1
2TerminatedTreatmentCancer, Ovarian / Fallopian Tube Cancer / Peritoneal Cavity Cancer1
2WithdrawnTreatmentHyperuricemia, Gout1
2, 3CompletedTreatmentDiabetes1
2, 3RecruitingTreatmentHeart Failure, Hyperuricemia1
2, 3RecruitingTreatmentJNC 7 Stage I Hypertension / Pre-Hypertension1
3Active Not RecruitingPreventionCoronary Artery Disease / Diabetic Nephropathies1
3Active Not RecruitingTreatmentCardiovascular Disease (CVD)1
3CompletedPreventionCancers / Hyperuricemia / Tumour lysis syndrome1
3CompletedPreventionTumour lysis syndrome1
3CompletedTreatmentAdult Acute Lymphocytic Leukemia / Lymphoma, High-Grade1
3CompletedTreatmentCardiovascular Disease (CVD) / Heart Diseases / Hypertensive1
3CompletedTreatmentDiabetic Autonomic Neuropathy1
3CompletedTreatmentGout Acute8
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Non-Hodgkin's Lymphoma (NHL)1
3CompletedTreatmentMania1
3CompletedTreatmentPatients With Grade II Ankle Sprain1
3RecruitingBasic ScienceType 2 Diabetes Mellitus1
3RecruitingTreatmentB Acute Lymphoblastic Leukemia1
3TerminatedTreatmentGout Acute1
3TerminatedTreatmentHyperuricemia1
3Unknown StatusTreatmentFetal Hypoxia / Reperfusion Injury1
4Active Not RecruitingPreventionComplications of Renal Transplant1
4Active Not RecruitingPreventionDiabetes, Diabetes Mellitus Type 1 / Diabetic Nephropathies1
4Active Not RecruitingTreatmentGout Acute1
4Active Not RecruitingTreatmentHypertensive / Left Ventricular Hypertrophy1
4CompletedPreventionBipolar Disorder (BD) / Mania / Mixed Mania1
4CompletedPreventionGout Acute / Impaired Renal Function1
4CompletedTreatmentAdenine Phosphoribosyltransferase Deficiency1
4CompletedTreatmentBipolar Disorder (BD) / Mixed Mania / Treatment-Resistant Mania1
4CompletedTreatmentChronic Heart Failure (CHF)1
4CompletedTreatmentChronic Heart Failure (CHF) / Hyperuricemia1
4CompletedTreatmentEnd Stage Renal Disease (ESRD) / Left Ventricular Hypertrophy1
4CompletedTreatmentGout Acute3
4CompletedTreatmentHeart Failure, Unspecified / Hyperuricemia1
4CompletedTreatmentHyperuricemia1
4CompletedTreatmentIntercritical Gout1
4CompletedTreatmentKidney Diseases / Left Ventricular Hypertrophy1
4CompletedTreatmentMania1
4CompletedTreatmentPeripheral Arterial Disease (PAD)1
4CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
4CompletedTreatmentSyndrome X1
4Enrolling by InvitationTreatmentSarcopenia1
4RecruitingBasic ScienceCardiovascular Disease (CVD)1
4RecruitingBasic ScienceChronic Gout / Hyperuricemia1
4RecruitingTreatmentChronic Kidney Disease (CKD) / Gout Acute1
4RecruitingTreatmentDiabetes Mellitus Type 2 Platelets Reactivity Statin1
4RecruitingTreatmentIschaemic Stroke1
4RecruitingTreatmentRenal Stones / Urolithiasis1
4TerminatedPreventionDiabetic Nephropathies1
4TerminatedTreatmentChronic, stable Angina pectoris1
Not AvailableActive Not RecruitingTreatmentKidney Diseases1
Not AvailableCompletedBasic ScienceBlood Pressures / BMI >27 kg/m2 / BMI >30 kg/m2 / Endothelial Function / Renal Function1
Not AvailableCompletedPreventionEndoscopic Retrograde Cholangiopancreatography1
Not AvailableCompletedScreeningChronic Kidney Disease (CKD) / Hyperuricemia1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Non-Hodgkin's Lymphoma (NHL)1
Not AvailableCompletedTreatmentIgA Nephropathy1
Not AvailableRecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Acute Myeloid Leukaemias (AML) / Myelodysplastic Syndrome1
Not AvailableUnknown StatusTreatmentIntrauterine Growth Retardation1
Not AvailableWithdrawnNot AvailableObstructive Sleep Apnea (OSA)1
Not AvailableWithdrawnTreatmentGout Acute1
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
Dosage forms
FormRouteStrength
TabletOral100 mg/1
TabletOral300 mg
TabletOral300 mg/1
Tablet, coatedOral100 mg/1
Tablet, coatedOral300 mg/1
TabletOral200 mg
Injection, powder, lyophilized, for solutionIntravenous500 mg/25mL
TabletOral100 mg
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)350 °CPhysProp
water solubility569 mg/L (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP-0.55BUNDGAARD,H & FALCH,E (1985)
logS-2.38ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility5.88 mg/mLALOGPS
logP-1.7ALOGPS
logP-1.8ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)7.83ChemAxon
pKa (Strongest Basic)2.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.85 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.24 m3·mol-1ChemAxon
Polarizability11.67 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
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-4900000000-5d6d365d7525c7325e01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-4900000000-ea448e075f973faea5ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000l-8900000000-98d308813f954ccc66e0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9300000000-a0c962d1b7e8e76fd526View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9100000000-d692c85314f5809e4758View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-01ox-9000000000-2662f35a8efe21c51958View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0900000000-4f38b316b66733e5ca8bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0900000000-547b3dac7e9b0d01ef66View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0900000000-43ea9e7d5a0f94da482fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-1900000000-fee6f9103fdd4cb1b6edView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01p9-1900000000-eb9ece2b9b724a6af483View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03dr-2900000000-85aef327ef1281780d05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-000i-7900000000-f5a7601a354a9d25428fView in MoNA
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPyrazolopyrimidines
Direct ParentPyrazolo[3,4-d]pyrimidines
Alternative ParentsPyrimidones / Vinylogous amides / Pyrazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives
SubstituentsPyrazolo[3,4-d]pyrimidine / Pyrimidone / Pyrimidine / Azole / Pyrazole / Vinylogous amide / Heteroaromatic compound / Azacycle / Organonitrogen compound / Organic oxygen compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptorsorganic heterobicyclic compound, nucleobase analogue (CHEBI:40279 ) / a small molecule (CPD-9024 )

Targets

Kind
Protein
Organism
Human
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. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
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. [PubMed:11752352 ]
  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. [PubMed:19584965 ]
  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. [PubMed:19654053 ]
  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. [PubMed:19436671 ]
  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. [PubMed:20029618 ]
  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. [PubMed:12184468 ]
  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. [PubMed:5415686 ]
  8. Okamoto K: [Inhibitors of xanthine oxidoreductase]. Nihon Rinsho. 2008 Apr;66(4):748-53. [PubMed:18409526 ]
  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. [PubMed:19376361 ]
  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. [PubMed:20046204 ]
  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. [PubMed:16507884 ]

Enzymes

Kind
Protein
Organism
Human
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, and vanillin. Plays a key role in the metabolism of xenobiotics and drugs containing aromatic azaheterocyclic substituents. Participates in the bioactivation of prodrugs such as famciclovir, catalyz...
Gene Name:
AOX1
Uniprot ID:
Q06278
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. [PubMed:8216357 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular Weight:
146422.99 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. [PubMed:8216357 ]

Transporters

Kind
Protein
Organism
Human
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, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
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. [PubMed:15100168 ]
Kind
Protein
Organism
Human
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 sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha-ketoglutarate.
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
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. [PubMed:12065749 ]
Drug created on June 13, 2005 07:24 / Updated on July 21, 2017 17:45