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

• ChemBase编号: 320
• 分子式: C5H4N4O
• 平均质量: 136.11146
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 1H,2H,4H-pyrazolo[3,4-d]pyrimidin-4-one
• IUPAC传统名: ALLO
• 商标名: 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
• 别名: Allopurinolum [INN-Latin]; Allopurinol Sodium; Alopurinol [INN-Spanish]; Allopurinol; Aloprim; Lopurin; Zyloprim; 1H-Pyrazolo[3,4-d]pyrimidin-4(5H)-one

登记号

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

理论计算性质

JChem

• Acid pKa: 7.828742
• 质子受体: 5
• 质子供体: 2
• LogD (pH = 5.5): -1.7607173
• LogD (pH = 7.4): -1.8863033
• Log P: -1.7583064
• 摩尔折射率: 54.2426 cm^3
• 极化性: 12.140558 Å^3
• 极化表面积: 65.85 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -1.72
• LOG S: -1.36
• 溶解度: 5.88e+00 g/l

分子性质

理化性质

• 溶解度: 569 mg/L
• 疏水性(logP): -1

安全信息

• 保存条件: -20°C

产品相关信息

• 纯度: 95%
• 成盐信息: Free Base

详细说明

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]

参考文献

• 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