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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-27 20:30:07 UTC
HMDB IDHMDB0014581
Secondary Accession Numbers
  • HMDB14581
Metabolite Identification
Common NameAllopurinol
DescriptionAllopurinol is only found in individuals that have used or taken this drug. It is a xanthine oxidase inhibitor that decreases uric acid production. It also acts as an antimetabolite on some simpler organisms. [PubChem]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.
Structure
Data?1582753195
Synonyms
ValueSource
1,5-Dihydro-4H-pyrazolo(3,4-D)pyrimidin-4-oneChEBI
1,5-Dihydro-4H-pyrazolo(3,4-D)pyrimidine-4-oneChEBI
1H-Pyrazolo(3,4-D)pyrimidin-4-olChEBI
4'-Hydroxypyrazolol(3,4-D)pyrimidineChEBI
4-HPPChEBI
4-Hydroxy-1H-pyrazolo(3,4-D)pyrimidineChEBI
4-Hydroxy-3,4-pyrazolopyrimidineChEBI
4-Hydroxypyrazolo(3,4-D)pyrimidineChEBI
4-HydroxypyrazolopyrimidineChEBI
4-Hydroxypyrazolyl(3,4-D)pyrimidineChEBI
4H-Pyrazolo(3,4-D)pyrimidin-4-oneChEBI
AL-100ChEBI
AllopurinolumChEBI
AlopurinolChEBI
ZyloprimChEBI
Allopurinol alphapharm brandHMDB
Allopurinol basf brandHMDB
Allopurinol merz brandHMDB
Allopurinol pharmafarm brandHMDB
Allopurinol roche brandHMDB
Allopurinol tad brandHMDB
Allopurinol thiemann brandHMDB
Allopurinol wellcome brandHMDB
Ashbourne brand OF allopurinolHMDB
Boots brand OF allopurinolHMDB
Fawns and mcallan brand OF allopurinolHMDB
FoliganHMDB
HamarinHMDB
Hennig brand OF allopurinolHMDB
Horner brand OF allopurinolHMDB
Jenapharm brand OF allopurinolHMDB
MiluritHMDB
MiluriteHMDB
Quimica, panHMDB
RemidHMDB
Rima brand OF allopurinolHMDB
RimapurinolHMDB
Rougier brand OF allopurinolHMDB
Thiemann brand OF allopurinolHMDB
UrtiasHMDB
XanturicHMDB
AllohexanHMDB
Allopurinol horner brandHMDB
Allopurinol merckle brandHMDB
Allopurinol multipharma brandHMDB
Allopurinol nicholas brandHMDB
Allopurinol novopharm brandHMDB
Allopurinol r.a.n. brandHMDB
Allopurinol rima brandHMDB
AlluralHMDB
Amrad brand OF allopurinolHMDB
AtisurilHMDB
Clonmel brand OF allopurinolHMDB
EmbarinHMDB
Glaxo wellcome brand OF allopurinolHMDB
ICN brand OF allopurinolHMDB
Merz brand OF allopurinolHMDB
Multipharma brand OF allopurinolHMDB
Nicholas brand OF allopurinolHMDB
PurinolHMDB
Rhône-poulenc rorer brand OF allopurinolHMDB
Rosen brand OF allopurinolHMDB
SuspendolHMDB
TAD brand OF allopurinolHMDB
TipuricHMDB
UripurinolHMDB
Wellcome brand OF allopurinolHMDB
XanthomaxHMDB
APS brand OF allopurinolHMDB
AlloprinHMDB
Allopurinol ashbourne brandHMDB
Allopurinol clonmel brandHMDB
Allopurinol douglas brandHMDB
Allopurinol hennig brandHMDB
Allopurinol hexal brandHMDB
Allopurinol rosen brandHMDB
Allopurinol gepepharm brandHMDB
AllparginHMDB
Alphapharm brand OF allopurinolHMDB
ApulongaHMDB
ApurinHMDB
BASF brand OF allopurinolHMDB
BleminolHMDB
Boehringer mannheim brand OF allopurinolHMDB
Byk gulden brand OF allopurinolHMDB
CapurateHMDB
Dorsch brand OF allopurinolHMDB
Douglas brand OF allopurinolHMDB
Hexal brand OF allopurinolHMDB
JenapurinolHMDB
Merckle brand OF allopurinolHMDB
NovopurolHMDB
Pan quimicaHMDB
PureductHMDB
Rhône poulenc rorer brand OF allopurinolHMDB
Roche brand OF allopurinolHMDB
RoucolHMDB
UrosinHMDB
Gepepharm brand OF allopurinolHMDB
AllohexalHMDB
AllopurinHMDB
Allopurinol aps brandHMDB
Allopurinol amrad brandHMDB
Allopurinol azupharma brandHMDB
Allopurinol bicther brandHMDB
Allopurinol boots brandHMDB
Allopurinol dorsch brandHMDB
Allopurinol icn brandHMDB
Allopurinol jenapharm brandHMDB
Allopurinol pinewood brandHMDB
Allopurinol protea brandHMDB
Allopurinol rougier brandHMDB
AllorinHMDB
Azupharma brand OF allopurinolHMDB
Bicther brand OF allopurinolHMDB
CaplenalHMDB
CellidrinHMDB
Henning berlin brand OF allopurinolHMDB
LopurinHMDB
LysuronHMDB
Novopharm brand OF allopurinolHMDB
Pharmafarm brand OF allopurinolHMDB
Pinewood brand OF allopurinolHMDB
ProgoutHMDB
Protea brand OF allopurinolHMDB
R.A.N. brand OF allopurinolHMDB
Reig jofre brand OF allopurinolHMDB
UribenzHMDB
UridocidHMDB
ZygoutHMDB
ZyloricHMDB
Chemical FormulaC5H4N4O
Average Molecular Weight136.1115
Monoisotopic Molecular Weight136.03851077
IUPAC Name1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one
Traditional NameALLO
CAS Registry Number315-30-0
SMILES
O=C1N=CN=C2NNC=C12
InChI Identifier
InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
InChI KeyOFCNXPDARWKPPY-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrazolopyrimidines
Sub ClassPyrazolo[3,4-d]pyrimidines
Direct ParentPyrazolo[3,4-d]pyrimidines
Alternative Parents
Substituents
  • Pyrazolo[3,4-d]pyrimidine
  • Pyrimidone
  • Pyrimidine
  • Azole
  • Pyrazole
  • Vinylogous amide
  • Heteroaromatic compound
  • Azacycle
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point350 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility5.88 g/LNot Available
LogP-1Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.88 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity54.24 m³·mol⁻¹ChemAxon
Polarizability11.67 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0550-8900000000-225d53e43d6b82e006bfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-4900000000-5d6d365d7525c7325e01Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-4900000000-ea448e075f973faea5ecSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000l-8900000000-98d308813f954ccc66e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9300000000-a0c962d1b7e8e76fd526Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9100000000-d692c85314f5809e4758Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-01ox-9000000000-2662f35a8efe21c51958Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0900000000-4f38b316b66733e5ca8bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0900000000-547b3dac7e9b0d01ef66Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-0900000000-43ea9e7d5a0f94da482fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-1900000000-fee6f9103fdd4cb1b6edSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-01p9-1900000000-eb9ece2b9b724a6af483Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-03dr-2900000000-85aef327ef1281780d05Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-1eb7584dbb0630e49004Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1900000000-4e5cd23deb565d2f87e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-07wc-9200000000-214c548ad4d15f5bfbf4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-b7681f9e17751c711d37Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-2900000000-a7c487c6207a07bf2903Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-af7211d0cc75dda0b005Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-7900000000-f5a7601a354a9d25428fSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00437 details
UrineDetected and Quantified18-23 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00437 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified630 umol/mmol creatinineAdult (>18 years old)BothMolybdenum cofactor deficiency details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease References
Molybdenum cofactor deficiency
  1. Wevers RA, Engelke UF, Moolenaar SH, Brautigam C, de Jong JG, Duran R, de Abreu RA, van Gennip AH: 1H-NMR spectroscopy of body fluids: inborn errors of purine and pyrimidine metabolism. Clin Chem. 1999 Apr;45(4):539-48. [PubMed:10102915 ]
Associated OMIM IDsNone
DrugBank IDDB00437
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2010
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAllopurinol
METLIN IDNot Available
PubChem Compound2094
PDB IDNot Available
ChEBI ID40279
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. 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 ]
  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. 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 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
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 ]
General function:
Involved in oxidoreductase activity
Specific function:
Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Has also low oxidase activity towards aldehydes (in vitro).
Gene Name:
XDH
Uniprot ID:
P47989
Molecular weight:
146422.99
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 ]
  12. 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

General function:
Involved in transmembrane transport
Specific function:
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulfate, allopurinol, 5-fluorouracil, paclitaxel, L-ascorbic acid, salicylate, ethotrexate, and alpha- ketoglutarate
Gene Name:
SLC22A7
Uniprot ID:
Q9Y694
Molecular weight:
60025.0
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 ]