2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-1H-purin-6-one

• ChemBase编号: 44444
• 分子式: C8H11N5O3
• 平均质量: 225.20464
• 单一同位素质量: 225.08618924
• SMILES: c12c(ncn2COCCO)c(=O)[nH]c(n1)N
• Canonical SMILES: OCCOCn1cnc2c1nc(N)[nH]c2=O
• 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-1H-purin-6-one
• IUPAC传统名: acyclovir; 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-1H-purin-6-one; zovir
• 别名: Acyclovir; 2-amino-9-((2-hydroxyethoxy)methyl)-1H-purin-6(9H)-one; Activir; Avirax; Cycloviran; Geavir; Herpetad; Milavir; Soothelip; Supraviran; Virasorb; Mirolex; Virovir; Zyclir; Aciclovir; Aciclovir; Acycloguanosine; Zovirax; 9-[(2-Hydroxyethoxy)-methyl]guanine;Acyclovir; ACYCLOGUANOSINE; 9-[(2-Hydroxyethoxy)methyl]guanine; Acyclovir; Acycloguanosine

登记号

• CAS号: 59277-89-3
• EC号: 261-685-1
• MDL号: MFCD00057880
• PubChem SID: 24278078; 162049207
• PubChem CID: 2022

理论计算性质

• Acid pKa: 10.159839
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): -1.5496677
• LogD (pH = 7.4): -1.550233
• Log P: -1.5495676
• 摩尔折射率: 55.0668 cm^3
• 极化性: 19.994585 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

分子性质

理化性质

• 溶解度: 1 M HCl: soluble50 mg/mL; DMSO; DMSO: soluble7 mg/mL; H2O: soluble0.7 mg/mL
• 外观: white powder
• 熔点: 250°C
• 紫外吸收波长: ε1mM/256 nm 11.8

安全信息

• 保存条件: -20°C; Room Temperature (15-30°C)
• 保存注意事项: IRRITANT
• RTECS编号: UP0791400
• 德国WGK号: 2
• TSCA收录: false
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: human ... HV1S(3365), NP(4860)
• 生物活性机理: Aciclovir triphosphate competitively inhibits viral DNA polymerase and competes with the natural deoxyguanosine triphosphate, for incorporation into viral DNA.; and finally to the triphosphate by phosphoglycerate kinase, phosphoenolpyruvate carboxykinase, and pyruvate kinase.; Guanosine analog that acts as an antimetabolite.; Once incorporated, aciclovir triphosphate inhibits DNA synthesis by acting as a chain terminator.; Viral (HSV-1, HSV-2 and VZV) thymidine kinase converts aciclovir to the aciclovir monophosphate, which is then converted to the diphosphate by cellular guanylate kinase,

产品相关信息

• 纯度: >98%; ≥99% (HPLC)
• 成盐信息: Free Base
• 应用领域: Antiviral agent.; Used especially against herpes.

详细说明

MP Biomedicals - 02154713

(9-[(2-Hydroxyethoxy)- methyl]guanine;Acyclovir) This product inhibits the replication of cytomegalovirus by a mechanism that is independent of its phosphorylation by viral or cellular thymidine kinase. It can be used to induce apoptosis in cells tra

Selleck Chemicals - S1807

Research Area: Infection
Biological Activity:
Acyclovir is a synthetic nucleoside analogue active against herpesviruses. It is a guanosine analogue antiviral drug. Aciclovir differs from previous nucleoside analogues in that it contains only a partial nucleoside structure: the sugar ring is replaced by an open-chain structure. It is selectively converted into acyclo-guanosine monophosphate (acyclo-GMP) by viral thymidine kinase, which is far more effective (3000 times) in phosphorylation than cellular thymidine kinase. [1]

Sigma Aldrich - A4669

Application
Acycloguanosine has been used to study herpes simplex virus latency and reactivation, as well as HIV retrovirus reproduction. Acycloguanosine inhibits replication of cytomegalovirus by a mechanism that is independent of its phosphorylation by viral or cellular thymidine kinase.
Biochem/physiol Actions
Antiviral agent. Phosphorylation by herpes simplex virus thymidine kinase (HSV-TK) leads to the formation of acycloguanosine triphosphate that competitively inhibits the viral DNA polymerase.
Antiviral agent. Phosphorylation by herpes simplex virus thymidine kinase (HSV-TK) leads to the formation of acycloguanosine triphosphate that competitively inhibits the viral DNA polymerase. Acycloguanosine can be used to induce apoptosis in cells transfected with HSV-TK. Inhibits replication of cytomegalovirus by a mechanism that is independent of its phosphorylation by viral or cellular thymidine kinase.

参考文献

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