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
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
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 |
DescriptionCurator'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
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.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16507884
Curator's Comment: http://pubs.acs.org/doi/abs/10.1021/ja01585a023
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1929 |
2.9 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Secondary | ZYLOPRIM Approved UseINDICATIONS & 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 Date1966 |
|||
Secondary | ZYLOPRIM Approved UseINDICATIONS & 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 Date1966 |
|||
Primary | ZYLOPRIM Approved UseINDICATIONS & 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 Date1966 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10583019 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.46 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10583019 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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 Sources: https://pubmed.ncbi.nlm.nih.gov/23802435/ |
|||
Sources: https://pubmed.ncbi.nlm.nih.gov/23802435/ |
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 Sources: https://pubmed.ncbi.nlm.nih.gov/23802435/ |
||
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 Sources: https://pubmed.ncbi.nlm.nih.gov/23802435/ |
|||
Sources: https://pubmed.ncbi.nlm.nih.gov/23802435/ |
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 Sources: https://pubmed.ncbi.nlm.nih.gov/23802435/ |
||
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 Sources: https://pubmed.ncbi.nlm.nih.gov/23802435/ |
|||
Sources: https://pubmed.ncbi.nlm.nih.gov/23802435/ |
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 Sources: https://pubmed.ncbi.nlm.nih.gov/23802435/ |
||
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 Sources: https://pubmed.ncbi.nlm.nih.gov/23802435/ |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/allopurinol.html
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26968635
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
Edited
Mon Mar 31 17:37:02 GMT 2025
by
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Mon Mar 31 17:37:02 GMT 2025
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Record UNII |
428673RC2Z
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Record Status |
Validated (UNII)
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Record Version |
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EU-Orphan Drug |
EU/3/12/1076
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FDA ORPHAN DRUG |
22787
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NCI_THESAURUS |
C1637
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NCI_THESAURUS |
C921
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FDA ORPHAN DRUG |
68392
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C2564
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428673RC2Z
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Allopurinol sodium
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m1541
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23662349
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DTXSID401021473
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SUB30291
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CHEMBL1467
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428673RC2Z
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241-771-5
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108836
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DBSALT000350
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100000092723
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17795-21-0
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80566
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PRIMARY | RxNorm |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |