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Details

Stereochemistry ACHIRAL
Molecular Formula C5H3N4O.Na
Molecular Weight 158.0933
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALLOPURINOL SODIUM

SMILES

[Na+].O=C1N=CNC2=C1C=N[N-]2

InChI

InChIKey=PTJRZVJXXNYNLN-UHFFFAOYSA-M
InChI=1S/C5H4N4O.Na/c10-5-3-1-8-9-4(3)6-2-7-5;/h1-2H,(H2,6,7,8,9,10);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula C5H3N4O
Molecular Weight 135.1035
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.drugs.com/allopurinol.html | https://www.ncbi.nlm.nih.gov/pubmed/11137320 | http://pubs.acs.org/doi/abs/10.1021/ja01585a023 | https://www.ncbi.nlm.nih.gov/pubmed/16507884

Allopurinol is a xanthine oxidase inhibitor used to decrease high blood uric acid levels. Allopurinol is specifically used to prevent gout, prevent specific types of kidney stones, and for the high uric acid levels that can occur with chemotherapy. Allopurinol acts on purine catabolism, without disrupting the biosynthesis of purines. It reduces the production of uric acid by inhibiting the biochemical reactions immediately preceding its formation. Allopurinol is a structural analog of the natural purine base, hypoxanthine. It is an inhibitor of xanthine oxidase, the enzyme responsible for the conversion of hypoxanthine to xanthine and of xanthine to uric acid, the end product of purine metabolism in man. Allopurinol is metabolized to the corresponding xanthine analog, oxypurinol (Allopurinol), which also is an inhibitor of xanthine oxidase. Allopurinol is taken by mouth or injected into a vein. Common side effects, when used by mouth, include itchiness and rash. Common side effects when used by injection include vomiting and kidney problems.

Originator

Curator's Comment: http://pubs.acs.org/doi/abs/10.1021/ja01585a023

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.9 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
ZYLOPRIM

Approved Use

INDICATIONS & USAGE THIS IS NOT AN INNOCUOUS DRUG. IT IS NOT RECOMMENDED FOR THE TREATMENT OF ASYMPTOMATIC HYPERURICEMIA. Allopurinol tablets reduce serum and urinary uric acid concentrations. Its use should be individualized for each patient and requires an understanding of its mode of action and pharmacokinetics (see CLINICAL PHARMACOLOGY, CONTRAINDICATIONS, WARNINGS, and PRECAUTIONS). Allopurinol tablets are indicated in: -the management of patients with signs and symptoms of primary or secondary gout (acute attacks, tophi, joint destruction, uric acid lithiasis, and/or nephropathy). -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 tablets should be discontinued when the potential for overproduction of uric acid is no longer present. -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.

Launch Date

1966
Secondary
ZYLOPRIM

Approved Use

INDICATIONS & USAGE THIS IS NOT AN INNOCUOUS DRUG. IT IS NOT RECOMMENDED FOR THE TREATMENT OF ASYMPTOMATIC HYPERURICEMIA. Allopurinol tablets reduce serum and urinary uric acid concentrations. Its use should be individualized for each patient and requires an understanding of its mode of action and pharmacokinetics (see CLINICAL PHARMACOLOGY, CONTRAINDICATIONS, WARNINGS, and PRECAUTIONS). Allopurinol tablets are indicated in: -the management of patients with signs and symptoms of primary or secondary gout (acute attacks, tophi, joint destruction, uric acid lithiasis, and/or nephropathy). -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 tablets should be discontinued when the potential for overproduction of uric acid is no longer present. -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.

Launch Date

1966
Primary
ZYLOPRIM

Approved Use

INDICATIONS & USAGE THIS IS NOT AN INNOCUOUS DRUG. IT IS NOT RECOMMENDED FOR THE TREATMENT OF ASYMPTOMATIC HYPERURICEMIA. Allopurinol tablets reduce serum and urinary uric acid concentrations. Its use should be individualized for each patient and requires an understanding of its mode of action and pharmacokinetics (see CLINICAL PHARMACOLOGY, CONTRAINDICATIONS, WARNINGS, and PRECAUTIONS). Allopurinol tablets are indicated in: -the management of patients with signs and symptoms of primary or secondary gout (acute attacks, tophi, joint destruction, uric acid lithiasis, and/or nephropathy). -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 tablets should be discontinued when the potential for overproduction of uric acid is no longer present. -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.

Launch Date

1966
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3 μg/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALLOPURINOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
0.64 μg/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALLOPURINOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4.46 μg × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALLOPURINOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
ALLOPURINOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
no (co-administration study)
Comment: allopurinol in vivo on probes of CYP2C9, CYP2C19 and CYP2D6 metabolism suggest that there are no clinically relevant drug-drug interactions between the drugs metabolized by these enzymes and allopurinol when used concomitantly
no
no (co-administration study)
Comment: allopurinol in vivo on probes of CYP2C9, CYP2C19 and CYP2D6 metabolism suggest that there are no clinically relevant drug-drug interactions between the drugs metabolized by these enzymes and allopurinol when used concomitantly
no
no (co-administration study)
Comment: allopurinol in vivo on probes of CYP2C9, CYP2C19 and CYP2D6 metabolism suggest that there are no clinically relevant drug-drug interactions between the drugs metabolized by these enzymes and allopurinol when used concomitantly
no
no (co-administration study)
Comment: allopurinol in vivo on probes of CYP2C9, CYP2C19 and CYP2D6 metabolism suggest that there are no clinically relevant drug-drug interactions between the drugs metabolized by these enzymes and allopurinol when used concomitantly
no
no (co-administration study)
Comment: allopurinol in vivo on probes of CYP2C9, CYP2C19 and CYP2D6 metabolism suggest that there are no clinically relevant drug-drug interactions between the drugs metabolized by these enzymes and allopurinol when used concomitantly
no
no (co-administration study)
Comment: allopurinol in vivo on probes of CYP2C9, CYP2C19 and CYP2D6 metabolism suggest that there are no clinically relevant drug-drug interactions between the drugs metabolized by these enzymes and allopurinol when used concomitantly
no
no (co-administration study)
Comment: allopurinol in vivo on probes of CYP2C9, CYP2C19 and CYP2D6 metabolism suggest that there are no clinically relevant drug-drug interactions between the drugs metabolized by these enzymes and allopurinol when used concomitantly
PubMed

PubMed

TitleDatePubMed
Subjective sensation of heaviness in gout patients.
2000 Jun
Rat ventral prostate xanthine oxidase bioactivation of ethanol to acetaldehyde and 1-hydroxyethyl free radicals: analysis of its potential role in heavy alcohol drinking tumor-promoting effects.
2001
Eotaxin expression and eosinophil infiltrate in the liver of patients with drug-induced liver disease.
2001 Apr
Bioequivalence of allopurinol and its metabolite oxipurinol in two tablet formulations.
2001 Apr
Pharmacoeconomic considerations in the management of acute tumor lysis syndrome.
2001 Apr
Role of intravenous allopurinol in the management of acute tumor lysis syndrome.
2001 Apr
Allopurinol hypersensitivity syndrome associated with systemic cytomegalovirus infection and systemic bacteremia.
2001 Apr
Successful treatment of visceral leishmaniasis with allopurinol plus ketoconazole in an infant who developed pancreatitis caused by meglumine antimoniate.
2001 Apr
Photoreactivation of alloxanthine-inhibited xanthine oxidase.
2001 Apr
Xanthine oxidase-derived reactive oxygen metabolites contribute to liver necrosis: protection by 4-hydroxypyrazolo[3,4-d]pyrimidine.
2001 Apr 30
[Therapeutic criteria in hyperuricemia].
2001 Feb
Protective effect of allopurinol on hepatic energy metabolism in ischemic and reperfused rat liver.
2001 Feb
Tumor lysis syndrome in an infant with Langerhans cell histiocytosis successfully treated using continuous arteriovenous hemofiltration.
2001 Feb
Erythema-multiforme-like eruption from amoxycillin and allopurinol.
2001 Feb
Pancreas preservation with Celsior solution in a pig autotransplantation model: comparative study with University of Wisconsin solution.
2001 Feb-Mar
Randomized clinical study comparing UW and Celsior solution in liver preservation for transplantation: preliminary results.
2001 Feb-Mar
Loss of No-induced relaxation in abdominal aorta preserved in a Co-culture system.
2001 Feb-Mar
Production of free radicals measured by spin trapping during operations for stenosis of the carotid artery.
2001 Jan
Efficacy and safety of desensitization to allopurinol following cutaneous reactions.
2001 Jan
The multidrug resistance protein MRP1 mediates the release of glutathione disulfide from rat astrocytes during oxidative stress.
2001 Jan
Study on free radicals and pancreatic fibrosis--pancreatic fibrosis induced by repeated injections of superoxide dismutase inhibitor.
2001 Jan
Cypermethrin-induced oxidative stress in rat brain and liver is prevented by vitamin E or allopurinol.
2001 Jan 3
Type 1 glycogen storage disease and recurrent calcium nephrolithiasis.
2001 Jun
Allopurinol enhances adenine nucleotide levels and improves myocardial function in isolated hypoxic rat heart.
2001 Mar
Does xanthine oxidase contribute to the hydroxyl radical generation in ischemia and reperfusion of the cochlea?
2001 Mar
A randomized comparison between rasburicase and allopurinol in children with lymphoma or leukemia at high risk for tumor lysis.
2001 May 15
Patents

Sample Use Guides

In Vivo Use Guide
The dosage of Allopurinol to accomplish full control of gout and to lower serum uric acid to normal or near-normal levels varies with the severity of the disease. The average is 200 to 300 mg per day for patients with mild gout and 400 to 600 mg per day for those with moderately severe tophaceous gout. The appropriate dosage may be administered in divided doses or as a single equivalent dose with the 300 mg tablet. Dosage requirements in excess of 300 mg should be administered in divided doses. The minimal effective dosage is 100 to 200 mg daily and the maximal recommended dosage is 800 mg daily.
Route of Administration: Other
Primary rat osteoblast cells were obtained from 2-day-old neonatal Sprague-Dawley rats. Following isolation, cells were resuspended in Dulbecco's Modified Essential Medium, supplemented with 10% foetal calf serum (FCS), 2 mM L-glutamine, 100 U/ml penicillin, 100 mg/ml streptomycin and 0.25 mg/ml amphotericin (complete mixture abbreviated to DMEM). Cells were cultured for 2–4 days in a humidified atmosphere of 5% CO2–95% air at 37 °C in 75 cm2 flasks until confluent. Upon confluence, cells were sub-cultured into 24- well trays in DMEM supplemented with 2 mM β-glycerophosphate, 50 μg/ml ascorbic acid and 10 nM dexamethasone (supplemented DMEM), with half medium changes every 3 days. Osteoblasts were cultured in the presence of allopurinol and oxypurinol (1 nM–10 mM) to determine the effect on cell proliferation, differentiation, function and gene expression. For the bone formation experiments, cells were also treated with febuxostat and, as a positive control of an anabolic agent, BMP2 (0.1 mM). Unless stated, experiments were carried out at 2 time points during the osteoblast culture; day 7, which represents differentiating osteoblasts, and day 14 (mature, bone forming osteoblasts). All experiments were carefully pH-controlled because bone mineralisation is extremely sensitive to inhibition by acidosis
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:37:02 GMT 2025
Edited
by admin
on Mon Mar 31 17:37:02 GMT 2025
Record UNII
428673RC2Z
Record Status Validated (UNII)
Record Version
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Name Type Language
ALLOPURINOL SODIUM
ORANGE BOOK   WHO-DD  
Common Name English
NSC-108836
Preferred Name English
4H-PYRAZOLO(3,4-D)PYRIMIDIN-4-ONE, 1,5-DIHYDRO-, MONOSODIUM SALT
Common Name English
1,5-DIHYDRO-4H-PYRAZOLO(3,4-D)PYRIMIDIN-4-ONE, MONOSODIUM SALT
Common Name English
ALLOPURINOL SODIUM [ORANGE BOOK]
Common Name English
ALLOPURINOL SODIUM SALT [MI]
Common Name English
ALOPRIM
Common Name English
Allopurinol sodium [WHO-DD]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/12/1076
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
FDA ORPHAN DRUG 22787
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
NCI_THESAURUS C1637
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
NCI_THESAURUS C921
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
FDA ORPHAN DRUG 68392
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C2564
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
PRIMARY
DAILYMED
428673RC2Z
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
PRIMARY
WIKIPEDIA
Allopurinol sodium
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
PRIMARY
MERCK INDEX
m1541
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
PRIMARY Merck Index
PUBCHEM
23662349
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
PRIMARY
EPA CompTox
DTXSID401021473
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
PRIMARY
EVMPD
SUB30291
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
PRIMARY
ChEMBL
CHEMBL1467
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
PRIMARY
FDA UNII
428673RC2Z
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
PRIMARY
ECHA (EC/EINECS)
241-771-5
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
PRIMARY
NSC
108836
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PRIMARY
DRUG BANK
DBSALT000350
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PRIMARY
SMS_ID
100000092723
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
PRIMARY
CAS
17795-21-0
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
PRIMARY
RXCUI
80566
Created by admin on Mon Mar 31 17:37:02 GMT 2025 , Edited by admin on Mon Mar 31 17:37:02 GMT 2025
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY