Identification

Name
Allopurinol
Accession Number
DB00437  (APRD00435, DB03027)
Type
Small Molecule
Groups
Approved
Description

A xanthine oxidase inhibitor that decreases uric acid production. It also acts as an antimetabolite on some simpler organisms. Allopurinol is considered a standard treatment of hyperuricemia associated with gout. In August 2017, an oral combination agent Duzallo was approved by FDA as a dual-mechanism treatment of hyperuricemia in patients with uncontrolled gout. Duzallo contains allopurinol and Lesinurad, a recently FDA-approved URAT1 inhibitor indicated for the treatment of hyperuricemia associated with gout.

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 Key
Allopurinol Sodium428673RC2Z17795-21-0PTJRZVJXXNYNLN-UHFFFAOYSA-M
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
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
AlloprinTablet100 mgOralValeant Canada Lp Valeant Canada S.E.C.1979-12-312014-07-30Canada
AllopurinolTablet300 mg/1OralActavis Pharma Company2009-04-06Not applicableUs
AllopurinolTablet300 mg/1OralRemedy Repack2010-01-132018-10-23Us
AllopurinolTablet300 mg/1OralH. J. Harkins Company Inc2017-01-03Not applicableUs
AllopurinolTablet300 mg/1OralAidarex Pharmaceuticals LLC2009-04-06Not applicableUs
AllopurinolTablet300 mg/1OralCardinal Health2009-03-11Not applicableUs
AllopurinolTablet100 mg/1OralA-S Medication Solutions2009-04-06Not applicableUs
AllopurinolTablet300 mg/1Oralbryant ranch prepack2009-04-06Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AllopurinolTablet300 mg/1OralMajor2004-12-102013-09-30Us
AllopurinolTablet300 mg/1OralAvera McKennan Hospital2016-10-242018-07-09Us
AllopurinolTablet100 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2010-04-01Not applicableUs
AllopurinolTablet100 mg/1OralMc Kesson Contract Packaging1986-10-242017-09-30Us
AllopurinolTablet100 mg/1OralCardinal Health1987-01-092013-08-31Us
AllopurinolTablet100 mg/1OralPreferreed Pharmaceuticals Inc.2009-10-01Not applicableUs
AllopurinolTablet100 mg/1OralMylan Pharmaceuticals Inc.1986-10-24Not applicableUs
AllopurinolTablet300 mg/1OralBlenheim Pharmacal, Inc.2013-10-07Not applicableUs
AllopurinolTablet300 mg/1OralRanbaxy Inc.2011-06-06Not applicableUs
AllopurinolTablet100 mg/1OralRemedy Repack2010-12-022010-12-03Us
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
DuzalloAllopurinol (200 mg/1) + Lesinurad (200 mg/1)Tablet, film coatedOralIronwood Pharmaceuticals, Inc.2017-10-03Not applicableUs
DuzalloAllopurinol (300 mg/1) + Lesinurad (200 mg/1)Tablet, film coatedOralIronwood Pharmaceuticals, Inc.2017-10-03Not applicableUs
International/Other Brands
Adenock (Tanabe) / Allohexal / Alloril / Aluron / Milurit / Progout / Zyloric / Zyrik
Categories
UNII
63CZ7GJN5I
CAS number
315-30-0
Weight
Average: 136.1115
Monoisotopic: 136.03851077
Chemical Formula
C5H4N4O
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,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.

Associated Conditions
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.

TargetActionsOrganism
AXanthine dehydrogenase/oxidase
inhibitor
Human
Absorption

Approximately 80-90% absorbed from the gastrointestinal tract.

Volume of distribution
Not Available
Protein binding

Allopurinol and oxypurinol are not bound to plasma proteins

Metabolism

Hepatic

Route of elimination

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

Half life

1-3 hours

Clearance
Not Available
Toxicity

LD50=214 mg/kg (in mice)

Affected organisms
  • Humans and other mammals
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
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Allopurinol is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Allopurinol is combined with (S)-Warfarin.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Allopurinol.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Allopurinol is combined with 4-hydroxycoumarin.
6-O-benzylguanineThe serum concentration of 6-O-benzylguanine can be increased when it is combined with Allopurinol.
7-DeazaguanineThe serum concentration of 7-Deazaguanine can be increased when it is combined with Allopurinol.
7,9-DimethylguanineThe serum concentration of 7,9-Dimethylguanine can be increased when it is combined with Allopurinol.
8-azaguanineThe serum concentration of 8-azaguanine can be increased when it is combined with Allopurinol.
8-chlorotheophyllineThe serum concentration of 8-chlorotheophylline can be increased when it is combined with Allopurinol.
9-DeazaguanineThe serum concentration of 9-Deazaguanine can be increased when it is combined with Allopurinol.
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
Human Metabolome Database
HMDB0014581
KEGG Drug
D00224
PubChem Compound
2094
PubChem Substance
46508516
ChemSpider
2010
BindingDB
181133
ChEBI
40279
ChEMBL
CHEMBL1467
Therapeutic Targets Database
DAP000773
PharmGKB
PA448320
HET
7HP
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Allopurinol
ATC Codes
M04AA01 — AllopurinolM04AA51 — Allopurinol, combinations
AHFS Codes
  • 92:16.00 — Antigout Agents
MSDS
Download (75.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingBasic ScienceHyperuricemia1
0RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL)1
1CompletedBasic ScienceAcute Gouty Arthritis1
1CompletedBasic ScienceCardiovascular Disease (CVD) / Cardiovascular Risk Factors / Vasoconstriction1
1CompletedBasic ScienceCardiovascular Disease (CVD) / Cardiovascular Risk Factors / Vasodilation1
1CompletedTreatmentFasting State1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentInflammatory Bowel Diseases (IBD)1
1CompletedTreatmentLeukemias / Malignant Lymphomas / Multiple Myeloma (MM) / Myelodysplastic Syndromes / Plasma Cell Neoplasms1
1CompletedTreatmentTuberculosis Infection1
1Enrolling by InvitationTreatmentAcute Gouty Arthritis1
1Not Yet RecruitingBasic ScienceCardiovascular Disease (CVD) / Cardiovascular Risk Factors / Vasoconstriction1
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, 2RecruitingTreatmentTreatment of Arthritis1
1, 2WithdrawnBasic ScienceCardiovascular Disease (CVD) / Congestive Cardiomyopathy / Congestive Heart Failure (CHF) / Heart Diseases1
1, 2WithdrawnTreatmentHigh Blood Pressure (Hypertension) / Transplant, Kidney1
2Active Not RecruitingTreatmentChronic Lymphocytic Leukaemia (CLL)1
2CompletedPreventionAcute Gouty Arthritis1
2CompletedPreventionHand-foot Syndrome1
2CompletedPreventionHepatic Enzymes / Metabolic Syndrome Parameters / Systolic and Diastolic Blood Pressure Levels / Uric Acid Levels1
2CompletedPreventionMetabolic Syndromes1
2CompletedTreatmentAcute Gouty Arthritis5
2CompletedTreatmentAcute Gouty Arthritis / Hyperuricemia1
2CompletedTreatmentBMI >30 kg/m2 / Hyperuricemia / Pre-Hypertension1
2CompletedTreatmentCongestive Heart Failure (CHF)1
2CompletedTreatmentElevated Serum Uric Acid / Heart Failure, Unspecified1
2CompletedTreatmentGout and Hyperuricemia1
2CompletedTreatmentHigh Blood Pressure (Hypertension) / Severe Obstructive Sleep Apnea (Apnea Hypopnea Index > 30 Events/Hour)1
2CompletedTreatmentHypertension,Essential1
2CompletedTreatmentHyperuricemia, Gout1
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 RecruitingTreatmentHyperuricemia / Type 2 Diabetes Mellitus1
2RecruitingPreventionRenal Transplant Donor of Left Kidney / Renal Transplant Donor of Right Kidney1
2RecruitingTreatmentAcute Lymphocytic Leukemia (ALL) / Acute Myelogenous Leukaemia (AML) / Burkitt's Lymphoma / Chronic Chronic myelogenous leukemia / Chronic Lymphocytic Leukaemia (CLL) / Follicular Lymphoma (FL) / Hematological Diseases / Leukemia, Plasma Cell / Leukemia, Prolymphocytic / Lymphoma, B-Cell / Lymphoma, Lymphoblastic / Lymphoplasmacytic Lymphoma / Mantle Cell Lymphoma (MCL) / Multiple Myeloma (MM) / Myelodysplastic Syndromes / Myeloproliferative Syndromes / Non-Hodgkin's Lymphoma (NHL) / Small Lymphocytic Lymphoma (SLL)1
2RecruitingTreatmentChronic Lymphocytic Leukaemia (CLL) / Primary Lymphoid Haematopoietic Neoplasms / Small Lymphocytic Lymphoma (SLL)1
2RecruitingTreatmentLymphoblastic Leukemia, Acute, Childhood1
2RecruitingTreatmentMultiple Myeloma (MM)1
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 of the Ovary / Fallopian Tube Cancer / Peritoneal Cavity Cancer1
2, 3CompletedTreatmentDiabetes Mellitus (DM)1
2, 3CompletedTreatmentHeart Failure, Hyperuricemia1
2, 3CompletedTreatmentJNC 7 Stage I Hypertension / Pre-Hypertension1
3Active Not RecruitingPreventionCoronary Artery Disease / Diabetic Nephropathies1
3CompletedPreventionHyperuricemia / Malignancies / Tumour lysis syndrome1
3CompletedPreventionTumour lysis syndrome1
3CompletedTreatmentAcute Gouty Arthritis8
3CompletedTreatmentAdult Acute Lymphocytic Leukemia / Lymphoma, High-Grade1
3CompletedTreatmentCardiovascular Disease (CVD)1
3CompletedTreatmentCardiovascular Disease (CVD) / Heart Diseases / High Blood Pressure (Hypertension)1
3CompletedTreatmentDiabetic Autonomic Neuropathy1
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
3RecruitingTreatmentColitis Ulcerative Exacerbation / Ulcerative Colitis (UC)1
3RecruitingTreatmentHypoxic-Ischaemic Encephalopathy / Infant, Newborn, Diseases1
3TerminatedTreatmentAcute Gouty Arthritis1
3TerminatedTreatmentHyperuricemia1
3Unknown StatusTreatmentFetal Hypoxia / Reperfusion Injury1
4Active Not RecruitingBasic ScienceGout Chronic / Hyperuricemia1
4Active Not RecruitingPreventionComplications of Renal Transplant1
4Active Not RecruitingTreatmentAcute Gouty Arthritis1
4CompletedPreventionAcute Gouty Arthritis / Impaired Renal Function1
4CompletedPreventionDiabetes, Diabetes Mellitus Type 1 / Diabetic Nephropathies1
4CompletedTreatmentAcute Gouty Arthritis3
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
4CompletedTreatmentHeart Failure, Unspecified / Hyperuricemia1
4CompletedTreatmentHigh Blood Pressure (Hypertension) / Left Ventricular Hypertrophy1
4CompletedTreatmentHyperuricemia1
4CompletedTreatmentIntercritical Gout1
4CompletedTreatmentKidney Diseases / Left Ventricular Hypertrophy1
4CompletedTreatmentMania1
4CompletedTreatmentPeripheral Arterial Disease (PAD)1
4CompletedTreatmentRenal Stones / Urolithiasis1
4CompletedTreatmentSarcopenia1
4CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders1
4CompletedTreatmentSyndrome X1
4Not Yet RecruitingPreventionDiabetes Mellitus (DM) / Ischaemic Heart Diseases / Multi Vessel Coronary Artery Disease1
4RecruitingBasic ScienceCardiovascular Disease (CVD)1
4RecruitingTreatmentAcute Gouty Arthritis / Chronic Kidney Disease (CKD)1
4RecruitingTreatmentDiabetes Mellitus Type 2 Platelets Reactivity Statin1
4RecruitingTreatmentIschaemic Stroke1
4TerminatedPreventionBipolar Disorder (BD) / Mania / Mixed Mania1
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 AvailableNot Yet RecruitingTreatmentAcute Gouty Arthritis1
Not AvailableRecruitingNot AvailableDiabetic Nephropathies1
Not AvailableRecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / Leukemia Acute Myeloid Leukemia (AML) / Myelodysplastic Syndrome1
Not AvailableRecruitingTreatmentCoronary Artery Disease / Diabetes Mellitus (DM)1
Not AvailableUnknown StatusTreatmentIntrauterine Growth Retardation1
Not AvailableWithdrawnNot AvailableObstructive Sleep Apnea (OSA)1
Not AvailableWithdrawnTreatmentAcute Gouty Arthritis1

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
Tablet, coatedOral100 mg/1
Tablet, coatedOral300 mg/1
Injection, powder, lyophilized, for solutionIntravenous500 mg/25mL
TabletOral200 mg
Tablet, film coatedOral
TabletOral100 mg/1
TabletOral100 mg
TabletOral300 mg/1
TabletOral300 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.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US8283369No2012-10-092028-11-26Us
US8084483No2011-12-272029-08-17Us
US8357713No2013-01-222028-11-26Us
US8546437No2013-10-012029-04-29Us
US9216179No2015-12-222030-08-02Us
US8003681No2011-08-232025-08-25Us
US8546436No2013-10-012032-02-29Us
US9956205No2018-05-012031-12-28Us

Properties

State
Solid
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
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-000i-7900000000-f5a7601a354a9d25428f
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-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

Taxonomy

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
Pyrazolo[3,4-d]pyrimidine / Pyrimidone / Pyrimidine / Azole / Pyrazole / Vinylogous amide / Heteroaromatic compound / Azacycle / Organonitrogen compound / Organic oxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic 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. 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. [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...
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. [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. Ha...
Gene Name
XDH
Uniprot ID
P47989
Uniprot Name
Xanthine dehydrogenase/oxidase
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, 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. [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 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. [PubMed:12065749]

Drug created on June 13, 2005 07:24 / Updated on November 18, 2018 13:32