Chemical Component Summary

Name7-HYDROXY-PYRAZOLO[4,3-D]PYRIMIDINE
Identifiers1H-pyrazolo[3,4-e]pyrimidin-7-ol
FormulaC5 H4 N4 O
Molecular Weight136.111
TypeNON-POLYMER
Isomeric SMILESc1c2c(c(ncn2)O)[nH]n1
InChIInChI=1S/C5H4N4O/c10-5-4-3(1-8-9-4)6-2-7-5/h1-2H,(H,8,9)(H,6,7,10)
InChIKeyJFZSDNLQDTYVEE-UHFFFAOYSA-N

Chemical Details

Formal Charge0
Atom Count14
Chiral Atom Count0
Bond Count15
Aromatic Bond Count10

Drug Info: DrugBank

DrugBank IDDB00437 
NameAllopurinol
Groups approved
DescriptionGout is a disease that occurs by the deposition of monosodium urate crystals (MSU) in body tissues, especially around joints [A175942]. This disease has been well-documented in historical medical records and appears in the biographies of several prominent, historically recognized individuals [A175942]. 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 [A36705]. It was initially approved by the FDA in 1966 [L5674] and is now formulated by several manufacturers [L5677].
Synonyms
  • 4H-Pyrazolo(3,4-d)pyrimidin-4-one
  • Allopurinol sodium
  • 1,5-Dihydro-4H-pyrazolo(3,4-d)pyrimidine-4-one
  • 4-HPP
  • 4-Hydroxypyrazolopyrimidine
Brand Names
  • PMS-allopurinol
  • Purinol Tab 300mg
  • Mar-allopurinol
  • Nu-allopurinol
  • Novo-purol Tab 200 mg
IndicationAllopurinol is indicated in [FDA 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.
Categories
  • Antigout Preparations
  • Antimetabolites
  • Antioxidants
  • BCRP/ABCG2 Substrates
  • Drugs that are Mainly Renally Excreted
ATC-Code
  • M04AA01
  • M04AA51
CAS number315-30-0

Drug Targets

NameTarget SequencePharmacological ActionActions
Xanthine dehydrogenase/oxidaseMTADKLVFFVNGRKVVEKNADPETTLLAYLRRKLGLSGTKLGCGEGGCGA...unknowninhibitor
Aldehyde oxidaseMDRASELLFYVNGRKVIEKNVDPETMLLPYLRKKLRLTGTKYGCGGGGCG...unknownsubstrate
Xanthine dehydrogenase/oxidaseMTADKLVFFVNGRKVVEKNADPETTLLAYLRRKLGLSGTKLGCGEGGCGA...unknowninhibitor
Solute carrier family 22 member 8MTFSEILDRVGSMGHFQFLHVAILGLPILNMANHNLLQIFTAATPVHHCR...unknownsubstrate
Solute carrier family 22 member 7MGFEELLEQVGGFGPFQLRNVALLALPRVLLPLHFLLPIFLAAVPAHRCA...unknownsubstrate
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 135460353, 5281000, 83786