Allopurinol

• Catalog No.: DB00437
• CAS Number: 315-30-0
• M. F.: C5H4N4O
• M. W.: 136.11146

SYNONYMS

• IUPAC name: 1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one
• IUPAC Traditional name: ALLO
• Brand Name: Embarin; Atisuril; Apurin; Urbol; Alositol; Lopurin; 7HP; Ailural; Apurol; Bloxanth; Nektrohan; Purinol; Remid; Uriprim; Uritas; Xanturat; Zyloric; Adenock; Allopur; Allozym; Aloral; Aluline; Anoprolin; Anzief; Bleminol; Cellidrin; Cosuric; Dabroson; Foligan; HPP; Hamarin; Hexanuret; Takanarumin; Uricemil; Uripurinol; Urolit; Urosin; Urtias; Urtias 100; Allo-Puren; Allural; Aloprim; Apo-Allopurinol; Apulonga; Caplenal; Dabrosin; Dura Al; Epidropal; Epuric; Geapur; Gichtex; Gotax; Ketanrift; Ketobun-A; Ledopur; Lysuron; Milurit; Miniplanor; Monarch; Progout; Riball; Sigapurol; Suspendol; Urobenyl; Zyloprim; Allohexal
• Synonyms: Alopurinol [INN-Spanish]; Allopurinolum [INN-Latin]; Allopurinol Sodium

DATABASE IDS

• PubChem SID: 46508516
• CAS Number: 315-30-0
• PubChem CID: 2094

PROPERTIES

• Hydrophobicity(logP): -1
• Solubility: 569 mg/L

DETAILS

Description (English)

• Drug Groups: approved
• Description: A xanthine oxidase inhibitor that decreases uric acid production. It also acts as an antimetabolite on some simpler organisms. [PubChem]
• 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.
• Pharmacology: 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.
• Toxicity: LD₅₀=214 mg/kg (in mice)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Approximately 80-90% absorbed from the gastrointestinal tract.
• Half Life: 1-3 hours
• Protein Binding: Allopurinol and oxypurinol are not bound to plasma proteins
• Elimination: Approximately 20% of the ingested allopurinol is excreted in the feces.
• References: 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 synthesis--can 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]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• 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 synthesis--can 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