2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one

• ChemBase编号: 666
• 分子式: C8H11N5O3
• 平均质量: 225.20464
• 单一同位素质量: 225.08618924
• SMILES: O(Cn1c2[nH]c(nc(=O)c2nc1)N)CCO
• Canonical SMILES: Nc1nc(=O)c2c([nH]1)n(COCCO)cn2
• InChI: InChI=1S/C8H11N5O3/c9-8-11-6-5(7(15)12-8)10-3-13(6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15)
• InChIKey: MKUXAQIIEYXACX-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one
• IUPAC传统名: zovirax; aciclovir
• 商标名: Alti-Acyclovir; Avirax; Vipral; Virorax; Zovir; Zovirax; Zovirax topical
• 别名: Wellcome-248u; Acycloguanosine; Acyclovir Sodium; AC2; Aciclovier; Acyclovir; Aciclovir Sodium; 9-Hyroxyethoxymethylguanine; Aciclovir; 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one; Acyclovir

登记号

• CAS号: 59277-89-3
• MDL号: MFCD00057880
• PubChem SID: 160964129; 46506002
• PubChem CID: 2022
• CHEBI ID: 2453
• ATC码: J05AB01; D06BB03; S01AD03
• CHEMBL: 184
• Chemspider ID: 1945
• DrugBank ID: DB00787
• KEGG ID: D00222
• 美国药典/FDA物质标识码: X4HES1O11F
• 维基百科标题: Aciclovir
• Medline Plus: a681045

理论计算性质

JChem

• Acid pKa: 7.9866085
• 质子受体: 7
• 质子供体: 3
• LogD (pH = 5.5): -1.0340011
• LogD (pH = 7.4): -1.1266081
• Log P: -1.0319568
• 摩尔折射率: 54.6334 cm^3
• 极化性: 20.181852 Å^3
• 极化表面积: 114.76 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -0.95
• LOG S: -1.39
• 溶解度: 9.08e+00 g/l

分子性质

理化性质

• 溶解度: 1.62 mg/mL at 22 oC [KRISTL,A et al. (1993)]
• 熔点: 256.5°C (493.7°F)
• 疏水性(logP): -1.56 [KRISTL,A ET AL. (1993)]; -2.605

药理学性质

• 给药途径: Intravenous, oral, topical
• 生物利用度: 10–20% (oral)
• 排泄: Renal
• 半衰期: 2.2–20 hours
• 代谢: Viral thymidine kinase
• 蛋白结合率: 9–33%
• 法定药品分级: POM (UK); Rx-only (US); S4 (Australia)
• 妊娠期药物分类: B (US); B3 (Australia)
• 美国（FDA）药品许可证: Acyclovir

产品相关信息

• 纯度: 95%; 98%

详细说明

DrugBank - DB00787

• Drug Groups: approved
• Description: A guanosine analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes. [PubChem]
• Indication: For the treatment and management of herpes zoster (shingles), genital herpes, and chickenpox
• Pharmacology: Aciclovir (INN) or acyclovir (USAN, former BAN) is a synthetic deoxyguanosine analog and it is the prototype antiviral agent that is activated by viral thymidine kinase. The selective activity of aciclovir is due to its affinity for the thymidine kinase enzyme encoded by HSV and VZV.
• Toxicity: Aciclovir may cause nephrotoxicity (crystallization of aciclovir within renal tubules, elevation of serum creatinine, transient), and neurotoxicity (coma, hallucinations, lethargy, seizures, tremors). Nephrotoxicity and neurotoxicity usually resolve after cessation of aciclovir therapy. However, there is no well-defined relationship between aciclovir concentrations in the blood and these adverse effects.
• Affected Organisms: Human Herpes Virus
• Biotransformation: Hepatic, the only major urinary metabolite that has been detected is 9-carboxymethoxymethylguanine.
• Absorption: Oral: bioavailability 10 to 20%
• Half Life: 2.5-3.3 hours
• Protein Binding: 9%-33%
• Elimination: Acyclovir is cleared renally.
• References: O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. Pubmed