3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione

• ChemBase编号: 685
• 分子式: C13H18N4O3
• 平均质量: 278.30702
• 单一同位素质量: 278.13789046
• SMILES: O=c1n(CCCCC(=O)C)c(=O)n(c2ncn(c12)C)C
• Canonical SMILES: CC(=O)CCCCn1c(=O)c2n(C)cnc2n(c1=O)C
• InChI: InChI=1S/C13H18N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8H,4-7H2,1-3H3
• InChIKey: BYPFEZZEUUWMEJ-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• IUPAC传统名: pentoxifylline; 3,7-dimethyl-1-(5-oxohexyl)purine-2,6-dione; 3,7-dimethyl-1-(5-oxohexyl)-2,3,6,7-tetrahydro-1H-purine-2,6-dione
• 商标名: Azupentat; Dimethyloxohexylxanthine; Durapental; Oxpentifylline; PENTOXYPHYLINE; Pentoxifyllin; Pentoxil; Pentoxiphyllium; Pentoxyfylline; Pentoxyphylline; Rentylin; Torental; Trental; Vazofirin
• 别名: pentoxifylline; EHT0201; Pentoxifylline; 3,7-dimethyl-1-(5-oxohexyl)-1H-purine-2,6(3H,7H)-dione; Trental; cis-9-Octadecenoyl coenzyme A; OLEOYL COENZYME A DIPOTASSIUM SALT; 3,7-Dihydro-3,7-dimethyl-1-(5-oxohexyl)-1H-purine-2,6-dione; 1-(5-Oxohexyl)-3,7-dimethylxanthine; 1-(5-Oxohexyl)Theobromine; Oxpentifylline; Vasotal; Vazofirin; Torental; Pentoxyphyllin; Pexal; Agapurin; Azupentat; Pentoflux; Pentoxifylline

登记号

• CAS号: 6493-05-6
• EC号: 229-374-5
• PubChem SID: 46505940; 160964148
• PubChem CID: 4740

理论计算性质

JChem

• Acid pKa: 19.642868
• 质子受体: 4
• 质子供体: 0
• LogD (pH = 5.5): 0.23220569
• LogD (pH = 7.4): 0.23220584
• Log P: 0.23220585
• 摩尔折射率: 73.5223 cm^3
• 极化性: 27.121319 Å^3
• 极化表面积: 75.51 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.08
• LOG S: -1.73
• 溶解度: 5.17e+00 g/l

分子性质

理化性质

• 溶解度: 77 mg/mL; Chloroform; Methanol; Water
• 外观: White to Off-White Solid
• 熔点: 104-106°C; 98-100°C
• 疏水性(logP): 0

安全信息

• 保存条件: 0°C; Refrigerator; Room Temperature (15-30°C)
• RTECS编号: XH2475000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 危险公开号: R:22
• 安全公开号: S:36/37/39

药理学性质

• 作用靶点: Others
• 生物活性机理: Along with erythrocyte activity, pentoxifylline also decreases blood viscosity by reducing plasma fibrinogen concentrations and increasing fibrinolytic activity; Inhibits erythrocyte phosphodiesterase, resulting in an increase in erythrocyte cAMP activity. Subsequently, the erythrocyte membrane becomes more resistant to deformity

产品相关信息

• 纯度: 90-95%
• 成盐信息: Free Base
• 应用领域: It also helps prevent strokes, can be used in managing sickle cell disease and improves blood flow to the brain; It is used to treat intermittent claudication resulting from obstructed arteries in the limbs, and vascular dementia; Pentoxifylline has also been used to treat nausea and headaches in the mountains (altitude sickness).; Pentoxifylline improves blood flow through blood vessels and therefore helps with blood circulation in the arms and legs (e.g. intermittent claudication)

详细说明

MP Biomedicals - 02156107

Phosphodiesterase inhibitor. Also blocks synthesis of Tumor Necrosis Factor-α.

MP Biomedicals - 02100904

Potassium Salt
Purity: 90-95%

DrugBank - DB00806

• Drug Groups: approved; investigational
• Description: A methylxanthine derivative that inhibits phosphodiesterase and affects blood rheology. It improves blood flow by increasing erythrocyte and leukocyte flexibility. It also inhibits platelet aggregation. Pentoxifylline modulates immunologic activity by stimulating cytokine production. [PubChem]
• Indication: For the treatment of patients with intermittent lameness or immobility arising from chronic occlusive arterial disease of the limbs.
• Pharmacology: Pentoxifylline, a synthetic dimethylxanthine derivative structurally related to theophylline and caffeine, is used in the treatment of peripheral vascular diseases and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy.
• Toxicity: LD₅₀=1385 mg/kg(orally in mice)
• Affected Organisms: Humans and other mammals
• Half Life: 0.4-0.8 hours
• Protein Binding: 70%
• Elimination: Excretion is almost totally urinary; the main biotransformation product is Metabolite V. Essentially no parent drug is found in the urine.
• References: : European Pentoxifylline Multi-Infarct Dementia Study. Eur Neurol. 1996;36(5):315-21. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - P276500

A metabolite of Pentifylline. Methylxanthine derivative that improves blood flow by decreasing blood viscosity. Phosphodiesterase inhibitor. Inhibits the synthesis of tumor necrosis factor α (TNF-α).

参考文献

• : European Pentoxifylline Multi-Infarct Dementia Study. Eur Neurol. 1996;36(5):315-21. Pubmed
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