1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one

• ChemBase ID: 320
• Molecular Formular: C5H4N4O
• Molecular Mass: 136.11146
• Monoisotopic Mass: 136.03851077
• SMILES: O=c1ncnc2[nH][nH]cc12
• Canonical SMILES: O=c1ncnc2c1c[nH][nH]2
• InChI: InChI=1S/C5H4N4O/c10-5-3-1-8-9-4(3)6-2-7-5/h1-2H,(H2,6,7,8,9,10)
• InChIKey: OFCNXPDARWKPPY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one
• IUPAC Traditional name: ALLO
• Brand Name: 7HP; Adenock; Ailural; Allo-Puren; 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; HPP; Hamarin; Hexanuret; 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; Allohexal
• Synonyms: Allopurinolum [INN-Latin]; Allopurinol Sodium; Alopurinol [INN-Spanish]; Allopurinol; Aloprim; Lopurin; Zyloprim; 1H-Pyrazolo[3,4-d]pyrimidin-4(5H)-one

Database IDs

• CAS Number: 315-30-0
• MDL Number: MFCD00599413
• PubChem SID: 160963783; 46508516
• PubChem CID: 2094

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.828742
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -1.7607173
• LogD (pH = 7.4): -1.8863033
• Log P: -1.7583064
• Molar Refractivity: 54.2426 cm^3
• Polarizability: 12.140558 Å^3
• Polar Surface Area: 65.85 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.72
• LOG S: -1.36
• Solubility (Water): 5.88e+00 g/l

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: -20°C

Product Information

• Purity: 95%
• Salt Data: Free Base

DETAILS

DrugBank - DB00437

• 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

Selleck Chemicals - S1630

Research Area: Neurological Disease
Biological Activity:
Allopurinol (Zyloprim) is a xanthine oxidase inhibitor with an IC50 of 7.82±0.12 µM.Xanthine oxidase is responsible for the successive oxidation of hypoxanthine and xanthine resulting in the production of uric acid, the product of human purine metabolism. [1] The inhibition of XO activity by 6-aminopurine (IC50=10.89±0.13 µM) and its analogues was compared with that by allopurinol (IC50=7.82±0.12 µM). Among these analogues, 2-chloro-6(methylamino)purine (IC50=10.19±0.10 µM) and 4-aminopyrazolo[3,4-d] pyrimidine (IC50=30.26±0.23 µM) were found to be potent inhibitors of XO. [2]

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
• http://en.wikipedia.org/wiki/Allopurinol