(8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,6H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-ol

• ChemBase编号: 434
• 分子式: C11H16N4O4
• 平均质量: 268.26914
• 单一同位素质量: 268.11715501
• SMILES: [C@@H]1(C[C@@H]([C@H](O1)CO)O)n1c2N=CNC[C@H](c2nc1)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1cnc2c1N=CNC[C@H]2O
• InChI: InChI=1S/C11H16N4O4/c16-3-8-6(17)1-9(19-8)15-5-14-10-7(18)2-12-4-13-11(10)15/h4-9,16-18H,1-3H2,(H,12,13)/t6-,7+,8+,9+/m0/s1
• InChIKey: FPVKHBSQESCIEP-JQCXWYLXSA-N

名称和登记号

名称

• IUPAC标准名: (8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,6H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-ol
• IUPAC传统名: (8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-ol
• 商标名: Co-V; Co-Vidarabine; Covidarabine; Nipent; PD-ADI; Vidarbine; Vira a Deaminase Inhibitor
• 别名: 2'-DCF; 2'-Deoxycoformycin; 2'-Dexoycoformycin; Deoxycoformycin; pentostatin; Pentostatin

登记号

• CAS号: 53910-25-1
• PubChem SID: 160963897; 46507116
• PubChem CID: 439693

理论计算性质

JChem

• Acid pKa: 13.062051
• 质子受体: 7
• 质子供体: 4
• LogD (pH = 5.5): -3.7633858
• LogD (pH = 7.4): -2.9345255
• Log P: -2.016391
• 摩尔折射率: 64.9814 cm^3
• 极化性: 24.982864 Å^3
• 极化表面积: 112.13 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -2.03
• LOG S: -1.4
• 溶解度: 1.07e+01 g/l

分子性质

理化性质

• 溶解度: 30 mg/mL
• 疏水性(logP): -1.1

详细说明

DrugBank - DB00552

• Drug Groups: approved; investigational
• Description: A potent inhibitor of adenosine deaminase. The drug is effective in the treatment of many lymphoproliferative malignancies, particularly hairy-cell leukemia. It is also synergistic with some other antineoplastic agents and has immunosuppressive activity. [PubChem]
• Indication: For the treatment of hairy cell leukaemia refractory to alpha interferon.
• Pharmacology: Pentostatin is an antineoplastic anti-metabolite used in the treatment of several forms of leukemia including acute nonlymphocytic leukemia and hairy cell leukemia. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. It is a 6-thiopurine analogue of the naturally occurring purine bases hypoxanthine and guanine. Intracellular activation results in incorporation into DNA as a false purine base. An additional cytotoxic effect is related to its incorporation into RNA. Cytotoxicity is cell cycle phase-specific (S-phase).
• Toxicity: LD₅₀=128 mg/kg (mouse), side effects include lethargy, rash, fatigue, nausea and myelosuppression.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic, but only small amounts are metabolized.
• Absorption: Not absorbed orally, crosses blood brain barrier.
• Half Life: 5.7 hours (with a range between 2.6 and 16 hrs)
• Protein Binding: 4%
• Elimination: In man, following a single dose of 4 mg/m2 of pentostatin infused over 5 minutes, approximately 90% of the dose was excreted in the urine as unchanged pentostatin and/or metabolites as measured by adenosine deaminase inhibitory activity.
• Clearance: * 68 mL/min/m2
• References: [Link]
• External Links: Wikipedia; Drugs.com

参考文献

• Link