Allopurinol

CAS No:
315-30-0 Category:
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Product Details:

  • CAS No: 315-30-0
  • AHFC code: 32:00.0
  • Synonyms: Allopurinol Sodium Allopurinolum [INN-Latin] Alopurinol [INN-Spanish]
  • ATC Code: M04AA01
  • Chemical Formula: C17H19N5
  • Molecular Weight: 136.1115
  • Assay/Purity: Typically NLT 98%
  • DrugBank: DB00437 (APRD00435, DB03027)
  • SMILES: O=C1N=CN=C2NNC=C12
  • InChl: OFCNXPDARWKPPY-UHFFFAOYSA-N
  • PubChem: 2094
  • IUPAC: 1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one

Additional Details

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.
Mode 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.
Metabolism:
Hepatic
Toxicity:
LD50=214 mg/kg (in mice)
General Reference:
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 Schlesinger N: Diagnosing and treating gout: a review to aid primary care physicians. Postgrad Med. 2010 Mar;122(2):157-61. Pubmed Suzuki I, Yamauchi T, Onuma M, Nozaki S: Allopurinol, an inhibitor of uric acid synthesisãcan it be used for the treatment of metabolic syndrome and related disorders? Drugs Today (Barc). 2009 May;45(5):363-78. Pubmed Terkeltaub R: Update on gout: new therapeutic strategies and options. Nat Rev Rheumatol. 2010 Jan;6(1):30-8. Pubmed 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
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