9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one

• ChemBase编号: 776
• 分子式: C10H12N4O3
• 平均质量: 236.22728
• 单一同位素质量: 236.09094026
• SMILES: O1[C@@H](n2c3[nH]cnc(=O)c3nc2)CC[C@H]1CO
• Canonical SMILES: OC[C@@H]1CC[C@@H](O1)n1cnc2c1[nH]cnc2=O
• InChI: InChI=1S/C10H12N4O3/c15-3-6-1-2-7(17-6)14-5-13-8-9(14)11-4-12-10(8)16/h4-7,15H,1-3H2,(H,11,12,16)/t6-,7+/m0/s1
• InChIKey: BXZVVICBKDXVGW-NKWVEPMBSA-N

名称和登记号

名称

• IUPAC标准名: 9-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-3H-purin-6-one
• IUPAC传统名: didanosine
• 商标名: Videx; Videx EC
• 别名: DDI; Dideoxyinosine; Didanosine

登记号

• CAS号: 69655-05-6
• PubChem SID: 160964239; 46506255
• PubChem CID: 50599

理论计算性质

JChem

• Acid pKa: 6.9434805
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): -0.36833292
• LogD (pH = 7.4): -0.8817131
• Log P: -0.3516364
• 摩尔折射率: 58.5938 cm^3
• 极化性: 21.945131 Å^3
• 极化表面积: 88.74 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: -0.99
• LOG S: -1.55
• 溶解度: 6.58e+00 g/l

分子性质

理化性质

• 溶解度: 15.8 mg/mL
• 疏水性(logP): -0.2

详细说明

DrugBank - DB00900

• Drug Groups: approved
• Description: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. Didanosine is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase; ddI is then metabolized to dideoxyadenosine triphosphate, its putative active metabolite. [PubChem]
• Indication: For use, in combination with other antiretroviral agents, in the treatment of HIV-1 infection in adults.
• Pharmacology: Didanosine is a nucleoside reverse transcriptase inhibitor (NRTI) with activity against Human Immunodeficiency Virus Type 1 (HIV-1). Didanosine differs from other nucleoside analogues, as it does not have any of the regular bases, instead it has hypoxanthine attached to the sugar ring. Didanosine is phosphorylated to active metabolites that compete for incorporation into viral DNA. They inhibit the HIV reverse transcriptase enzyme competitively and act as a chain terminator of DNA synthesis. Didanosine is effective against HIV, and usually used in combination with other antiviral therapy. Switching from long term AZT treatment to didanosine has been shown to be beneficial. Didanosine has weak acid stability and therefore, it is often combined with an antacid.
• Toxicity: Side effects include pancreatitis, peripheral neuropathy, diarrhea, hyperuricemia and hepatic dysfunction
• Affected Organisms: Human Immunodeficiency Virus
• Biotransformation: Rapidly metabolized intracellularly to its active moiety, 2,3-dideoxyadenosine-5-triphosphate (ddA-TP). It is then further metabolized hepatically to yield hypoxanthine, xanthine, and uric acid.
• Absorption: Rapidly absorbed (bioavailability 30-40%) with peak plasma concentrations appearing within 0.5 and 1.5 hrs.
• Half Life: 30 minutes in plasma and more than 12 hours in intracellular environment.
• Protein Binding: Low (<5%)
• Elimination: Based on data from in vitro and animal studies, it is presumed that the metabolism of didanosine in man occurs by the same pathways responsible for the elimination of endogenous purines. Purines are eliminated by the kidneys.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com