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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Allopurinol (DB00437)

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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

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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 Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Used in combination to treat	Hyperuricemia	Combination Product in combination with: Benzbromarone (DB12319)	••••••••••••			••••••
Used in combination to treat	Hyperuricemia	Combination Product in combination with: Benzbromarone (DB12319)	••••••••••••			••••••
Used in combination to treat	Hyperuricemia	Combination Product in combination with: Benzbromarone (DB12319)	••••••••••••			••••••
Used in combination to treat	Hyperuricemia	Combination Product in combination with: Benzbromarone (DB12319)	••••••••••••			••••••
Used in combination to treat	Hyperuricemia	Combination Product in combination with: Benzbromarone (DB12319)	••••••••••••			••••••

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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.

Target	Actions	Organism
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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• Allopurinol
  • oxypurinol

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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Interacting Gene/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
HLA class I histocompatibility antigen protein P5	HLA-B*5801	(G;G) / (G;T)	G allele	ADR Directly Studied	Patients who carry this allele are at a higher risk of experiencing severe cutaneous adverse reactions when treated with allopurinol.	Details

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abacavir	Allopurinol may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abemaciclib	Abemaciclib may decrease the excretion rate of Allopurinol which could result in a higher serum level.
Aceclofenac	Aceclofenac may decrease the excretion rate of Allopurinol which could result in a higher serum level.
Acemetacin	Acemetacin may decrease the excretion rate of Allopurinol which could result in a higher serum level.
Acenocoumarol	The 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

Ingredient	UNII	CAS	InChI Key
Allopurinol sodium	428673RC2Z	17795-21-0	PTJRZVJXXNYNLN-UHFFFAOYSA-M

Product Images

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International/Other Brands

Adenock (Tanabe) / Allohexal / Alloril / Aluron / Milurit / Progout / Zyloric / Zyrik

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Alloprin	Tablet	200 mg	Oral	Valeant Canada Lp Valeant Canada S.E.C.	1981-12-31	2014-07-30
Alloprin	Tablet	100 mg	Oral	Valeant Canada Lp Valeant Canada S.E.C.	1979-12-31	2014-07-30
Alloprin	Tablet	300 mg	Oral	Valeant Canada Lp Valeant Canada S.E.C.	1980-12-31	2014-07-30
Allopurinol	Tablet	300 mg/1	Oral	Remedy Repack	2012-12-31	2013-12-31
Allopurinol	Tablet	100 mg/1	Oral	Proficient Rx LP	2009-04-06	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Ag-allopurinol	Tablet	200 mg	Oral	Angita Pharma Inc.	2019-09-20	Not applicable
Ag-allopurinol	Tablet	100 mg	Oral	Angita Pharma Inc.	2019-10-27	Not applicable
Ag-allopurinol	Tablet	300 mg	Oral	Angita Pharma Inc.	2019-09-20	Not applicable
Allopurinol	Tablet	100 mg/1	Oral	Mylan Institutional Inc.	1997-04-29	Not applicable
Allopurinol	Tablet	300 mg/1	Oral	Ranbaxy Inc.	2011-06-06	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
DUZALLO	Allopurinol (200 MG) + Lesinurad (200 MG)	Tablet, film coated	Oral	Grunenthal Gmbh	2019-01-29	2020-08-28
Duzallo	Allopurinol (300 mg/1) + Lesinurad (200 mg/1)	Tablet, film coated	Oral	Ironwood Pharmaceuticals, Inc.	2017-10-03	2019-11-30
DUZALLO	Allopurinol (300 MG) + Lesinurad (200 MG)	Tablet, film coated	Oral	Grunenthal Gmbh	2019-01-29	2020-08-28
DUZALLO	Allopurinol (200 MG) + Lesinurad (200 MG)	Tablet, film coated	Oral	Grunenthal Gmbh	2019-01-29	2020-08-28
Duzallo	Allopurinol (200 mg/1) + Lesinurad (200 mg/1)	Tablet, film coated	Oral	Ironwood Pharmaceuticals, Inc.	2017-10-03	2020-04-30

Categories

ATC Codes

M04AA01 — Allopurinol

• M04AA — Preparations inhibiting uric acid production
• M04A — ANTIGOUT PREPARATIONS
• M04 — ANTIGOUT PREPARATIONS
• M — MUSCULO-SKELETAL SYSTEM

M04AA51 — Allopurinol, combinations

• M04AA — Preparations inhibiting uric acid production
• M04A — ANTIGOUT PREPARATIONS
• M04 — ANTIGOUT PREPARATIONS
• M — MUSCULO-SKELETAL SYSTEM

Drug Categories

• Antigout Preparations
• Antimetabolites
• Antioxidants
• BCRP/ABCG2 Substrates
• Drugs that are Mainly Renally Excreted
• Enzyme Inhibitors
• Free Radical Scavengers
• Heterocyclic Compounds, Fused-Ring
• Musculo-Skeletal System
• OAT3/SLC22A8 Substrates
• Preparations Inhibiting Uric Acid Production
• Protective Agents
• Purines
• Uricosuric Agents
• Xanthine Oxidase Inhibitors

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]

External Links

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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Basic Science	Gout Chronic / Hyperuricemia	1
4	Completed	Prevention	Diabetic Nephropathy / Type 1 Diabetes Mellitus	1
4	Completed	Prevention	Gout / Impaired Renal Function	1
4	Completed	Treatment	Acute Coronary Syndrome (ACS)	1
4	Completed	Treatment	Acute Gouty Arthritis / Gout	1

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

Form	Route	Strength
Tablet	Oral	300 mg
Tablet	Oral
Injection, powder, lyophilized, for solution	Intravenous	500 mg/25mL
Tablet	Oral	100.00 mg
Tablet	Oral	200 mg
Tablet, effervescent
Granule	Oral	4.4 %
Granule, effervescent	Oral	300 mg
Tablet	Oral	150 MG
Tablet	Oral	10000000 mg
Tablet	Oral	100 MG
Tablet	Oral	300.00 mg
Tablet, film coated	Oral
Capsule	Oral
Tablet	Oral
Tablet	Oral	300.000 mg
Tablet, film coated	Oral
Tablet, soluble
Tablet	Oral	100 mg/1
Tablet	Oral	100.000 mg
Tablet	Oral	200 mg/1
Tablet	Oral	300 mg/1
Granule	Oral	300 MG
Tablet, coated	Oral

Prices

Unit description	Cost	Unit
Aloprim 500 mg vial	612.3USD	vial
Allopurinol sodium 500 mg vial	583.14USD	vial
Allopurinol powder	18.41USD	g
Zyloprim 300 mg tablet	1.89USD	tablet
Zyloprim 100 mg tablet	0.82USD	tablet
Allopurinol 300 mg tablet	0.46USD	tablet
Allopurinol 100 mg tablet	0.24USD	tablet
Apo-Allopurinol 300 mg Tablet	0.22USD	tablet
Novo-Purol 300 mg Tablet	0.22USD	tablet
Apo-Allopurinol 200 mg Tablet	0.14USD	tablet
Novo-Purol 200 mg Tablet	0.14USD	tablet
Apo-Allopurinol 100 mg Tablet	0.08USD	tablet
Novo-Purol 100 mg Tablet	0.08USD	tablet
Suspendol-s liquid	0.04USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
US8283369	No	2012-10-09	2028-11-26
US8084483	No	2011-12-27	2029-08-17
US8357713	No	2013-01-22	2028-11-26
US8546437	No	2013-10-01	2029-04-29
US9216179	No	2015-12-22	2030-08-02
US8003681	No	2011-08-23	2025-08-25
US8546436	No	2013-10-01	2032-02-29
US9956205	No	2018-05-01	2031-12-28
US10183012	No	2019-01-22	2028-11-26

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	>300	https://www.chemicalbook.com/ChemicalProductProperty_US_CB1181254.aspx
boiling point (°C)	250.36	https://www.chemicalbook.com/ChemicalProductProperty_US_CB1181254.aspx
water solubility	solubility in water at 37°C is 80.0 mg/dL and is greater in an alkaline solution	FDA label
logP	-1.8	http://www.t3db.ca/toxins/T3D3477
logS	-1.4	http://www.t3db.ca/toxins/T3D3477
pKa	10.2 (at 25℃)	https://www.chemicalbook.com/ChemicalProductProperty_US_CB1181254.aspx

Predicted Properties

Property	Value	Source
Water Solubility	22.0 mg/mL	ALOGPS
logP	-0.41	ALOGPS
logP	0.031	Chemaxon
logS	-0.79	ALOGPS
pKa (Strongest Acidic)	8.47	Chemaxon
pKa (Strongest Basic)	1.25	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	4	Chemaxon
Hydrogen Donor Count	2	Chemaxon
Polar Surface Area	74.69 Å2	Chemaxon
Rotatable Bond Count	0	Chemaxon
Refractivity	34.98 m3·mol-1	Chemaxon
Polarizability	11.7 Å3	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.997
Blood Brain Barrier	+	0.9885
Caco-2 permeable	-	0.6232
P-glycoprotein substrate	Non-substrate	0.7409
P-glycoprotein inhibitor I	Non-inhibitor	0.9135
P-glycoprotein inhibitor II	Non-inhibitor	0.9858
Renal organic cation transporter	Non-inhibitor	0.8653
CYP450 2C9 substrate	Non-substrate	0.8635
CYP450 2D6 substrate	Non-substrate	0.8256
CYP450 3A4 substrate	Non-substrate	0.6242
CYP450 1A2 substrate	Non-inhibitor	0.8817
CYP450 2C9 inhibitor	Non-inhibitor	0.9472
CYP450 2D6 inhibitor	Non-inhibitor	0.923
CYP450 2C19 inhibitor	Non-inhibitor	0.9198
CYP450 3A4 inhibitor	Non-inhibitor	0.858
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9169
Ames test	Non AMES toxic	0.7089
Carcinogenicity	Non-carcinogens	0.921
Biodegradation	Not ready biodegradable	0.9675
Rat acute toxicity	2.1087 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9511
hERG inhibition (predictor II)	Non-inhibitor	0.9448

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	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0550-8900000000-225d53e43d6b82e006bf
Mass Spectrum (Electron Ionization)	MS	splash10-000i-7900000000-f5a7601a354a9d25428f
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-000i-4900000000-5d6d365d7525c7325e01
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-000i-4900000000-ea448e075f973faea5ec
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-000l-8900000000-98d308813f954ccc66e0
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0006-9300000000-a0c962d1b7e8e76fd526
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0006-9100000000-d692c85314f5809e4758
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-01ox-9000000000-2662f35a8efe21c51958
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-000i-0900000000-4f38b316b66733e5ca8b
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-000i-0900000000-547b3dac7e9b0d01ef66
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-000i-0900000000-43ea9e7d5a0f94da482f
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-000i-1900000000-fee6f9103fdd4cb1b6ed
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-01p9-1900000000-eb9ece2b9b724a6af483
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-03dr-2900000000-85aef327ef1281780d05
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-0900000000-788ea071a3463cfeb449
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-0900000000-386b8a737e891fe218aa
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-1900000000-b2af8ac33acc74bcd787
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0aou-9400000000-aa0dbe7b305164d7937d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0uy1-9200000000-ad0f9bbce29a9c05d51d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00kr-9700000000-74aa713f214db290843e
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[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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Details1. Xanthine dehydrogenase/oxidase

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]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55