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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. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Allopurinol Sodium
Allopurinolum [INN-Latin]
Alopurinol [INN-Spanish]
Salts Not Available
Brand names
Name Company
7HP
Adenock
Ailural
Allo-Puren
Allohexal
Allopur
Allozym
Allural
Aloprim
Aloral
Alositol
Aluline
Anoprolin
Anzief
Apo-Allopurinol
Apulonga
Apurin
Apurol
Atisuril
Bleminol
Bloxanth
Caplenal
Cellidrin
Cosuric
Dabrosin
Dabroson
Dura Al
Embarin
Epidropal
Epuric
Foligan
Geapur
Gichtex
Gotax
Hamarin
Hexanuret
HPP
Ketanrift
Ketobun-A
Ledopur
Lopurin
Lysuron
Milurit
Miniplanor
Monarch
Nektrohan
Progout
Purinol
Remid
Riball
Sigapurol
Suspendol
Takanarumin
Urbol
Uricemil
Uriprim
Uripurinol
Uritas
Urobenyl
Urolit
Urosin
Urtias
Urtias 100
Xanturat
Zyloprim
Zyloric
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Brand mixtures Not Available
Categories
  • Free Radical Scavengers
  • Antimetabolites
  • Enzyme Inhibitors
  • Enzyme Inhibitors Antimetabolites
  • Gout Suppressants
CAS number 315-30-0
Weight Average: 136.1115
Monoisotopic: 136.03851077
Chemical Formula C5H4N4O
InChI Key InChIKey=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)
Plain Text
IUPAC Name
1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one
SMILES
O=C1N=CN=C2NNC=C12
Plain Text
Mass Spec show (7.32 KB)
Taxonomy
Kingdom Organic
Classes
  • Pyrazolopyrimidines
Substructures
  • Pyrazoles
  • Pyrimidines and Derivatives
  • Pyrazolopyrimidines
  • Heterocyclic compounds
  • Aromatic compounds
  • Cyanamides
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.
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.
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
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
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Aloprim 500 mg vial 612.3 USD vial
Allopurinol sodium 500 mg vial 583.14 USD vial
Allopurinol powder 18.41 USD g
Zyloprim 300 mg tablet 1.89 USD tablet
Zyloprim 100 mg tablet 0.82 USD tablet
Allopurinol 300 mg tablet 0.46 USD tablet
Allopurinol 100 mg tablet 0.24 USD tablet
Apo-Allopurinol 300 mg Tablet 0.22 USD tablet
Novo-Purol 300 mg Tablet 0.22 USD tablet
Apo-Allopurinol 200 mg Tablet 0.14 USD tablet
Novo-Purol 200 mg Tablet 0.14 USD tablet
Apo-Allopurinol 100 mg Tablet 0.08 USD tablet
Novo-Purol 100 mg Tablet 0.08 USD tablet
Suspendol-s liquid 0.04 USD ml
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 350 °C PhysProp
water solubility 569 mg/L (at 25 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP -0.55 BUNDGAARD,H & FALCH,E (1985)
logS -2.38 ADME Research, USCD
Predicted Properties
Property Value Source
water solubility 5.88e+00 g/l ALOGPS
logP -1.7 ALOGPS
logP -1.8 ChemAxon
logS -1.4 ALOGPS
pKa (strongest acidic) 7.83 ChemAxon
pKa (strongest basic) 2.57 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 5 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 65.85 ChemAxon
rotatable bond count 0 ChemAxon
refractivity 54.24 ChemAxon
polarizability 11.67 ChemAxon
References
Synthesis Reference Not Available
General Reference
  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
  2. Schlesinger N: Diagnosing and treating gout: a review to aid primary care physicians. Postgrad Med. 2010 Mar;122(2):157-61. Pubmed
  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. Pubmed
  4. Terkeltaub R: Update on gout: new therapeutic strategies and options. Nat Rev Rheumatol. 2010 Jan;6(1):30-8. Pubmed
  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
External Links
Resource Link
KEGG Drug D00224 Link_out
PubChem Compound 2094 Link_out
PubChem Substance 46508516 Link_out
ChemSpider 2010 Link_out
BindingDB 50241255 Link_out
ChEBI 40279 Link_out
ChEMBL 40279 Link_out
Therapeutic Targets Database DAP000773 Link_out
PharmGKB PA448320 Link_out
HET 7HP Link_out
Drug Product Database 555681 Link_out
RxList http://www.rxlist.com/cgi/generic/allopur.htm Link_out
Drugs.com http://www.drugs.com/allopurinol.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/zyl1508.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Allopurinol Link_out
ATC Codes
  • M04AA01
AHFS Codes
  • 92:00.00
PDB Entries
FDA label Not Available
MSDS show (75.9 KB)
Interactions
Drug Interactions
Drug Interaction
Acenocoumarol Allopurinol may increase the anticoagulant effect of acenocoumarol.
Anisindione Allopurinol may increase the anticoagulant effect of anisindione.
Azathioprine Allopurinol may increase the effect of thiopurine, azathioprine.
Cyclosporine Allopurinol increases the effect and toxicity of cyclosporine
Dicumarol Allopurinol may increase the anticoagulant effect of dicumarol.
Mercaptopurine Allopurinol may increase the effect of thiopurine, mercaptopurine.
Trandolapril The ACE inhibitor, Trandolapril, may increase the risk of hypersensitivity reactions to Allopurinol.
Warfarin Allopurinol may increase the anticoagulant effect of warfarin. Monitor for changes in prothrombin times and therapeutic effects of warfarin if allopurinol is initiated, discontinued or dose changed.
Food Interactions
  • Avoid alcohol.
  • Take with a full glass of water.
  • Take with food.
Targets

1. Xanthine dehydrogenase/oxidase

Pharmacological action: yes
Actions: inhibitor

This enzyme can be converted from the dehydrogenase form (D) to the oxidase form (O) irreversibly by proteolysis or reversibly through the oxidation of sulfhydryl groups

Organism class: human
UniProt ID: P47989 Link_out
Gene: XDH Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  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. Pubmed
  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. Epub 2009 Aug 3. Pubmed
  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
  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. Epub 2009 Nov 4. Pubmed
  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
  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
  8. Okamoto K: [Inhibitors of xanthine oxidoreductase] Nippon Rinsho. 2008 Apr;66(4):748-53. Pubmed
  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. Pubmed
  10. Terkeltaub R: Update on gout: new therapeutic strategies and options. Nat Rev Rheumatol. 2010 Jan;6(1):30-8. Pubmed
  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
Enzymes

1. Aldehyde oxidase

Actions: substrate

An aldehyde + H(2)O + O(2) = a carboxylic acid + H(2)O(2)

UniProt ID: Q06278 Link_out
Gene: AOX1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

2. Xanthine dehydrogenase/oxidase

Actions: substrate

This enzyme can be converted from the dehydrogenase form (D) to the oxidase form (O) irreversibly by proteolysis or reversibly through the oxidation of sulfhydryl groups

UniProt ID: P47989 Link_out
Gene: XDH Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Transporters

1. Solute carrier family 22 member 8

Actions: substrate

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, fexofenadine. Transports benzylpenicillin (PCG), estrone- 3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA)

UniProt ID: Q8TCC7 Link_out
Gene: SLC22A8 Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

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

2. Solute carrier family 22 member 7

Actions: substrate

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

UniProt ID: Q9Y694 Link_out
Gene: SLC22A7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19