(2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase编号: 79
• 分子式: C10H13N5O4
• 平均质量: 267.24132
• 单一同位素质量: 267.09675392
• SMILES: O1[C@@H](n2c3ncnc(N)c3nc2)[C@@H](O)[C@H](O)[C@H]1CO
• Canonical SMILES: OC[C@H]1O[C@H]([C@H]([C@@H]1O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C10H13N5O4/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(18)6(17)4(1-16)19-10/h2-4,6-7,10,16-18H,1H2,(H2,11,12,13)/t4-,6-,7+,10-/m1/s1
• InChIKey: OIRDTQYFTABQOQ-UHTZMRCNSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC传统名: armes
• 商标名: Arasena-A; Spongoadenosine; Vira-A; Vidarabin
• 别名: Vira-A; 9-β-D-Arabinofuranosyladenine; Vidarabine; Adenine 9-β-D-arabinofuranoside; Adenine Arabinoside; Arabinofuranosyladenine Triphosphate; Arabinoside Adenine; Arabinosyl Adenine; Arabinosyladenine; Arabinosyladenine Triphosphate; Vidarabine Triphosphate; Ara Atp; Ara-A; Ara-a Triphosphate; Ara-Atp; Araadenosine; Arabinosyl-Atp; 9-beta-D-arabinofuranosyl-adenine; Vidarabine; 6-Amino-9-b-D-arabinofuranosylpurine

登记号

• CAS号: 5536-17-4; 24356-66-9
• EC号: 226-893-9
• MDL号: MFCD00065471
• Beilstein号: 624881
• PubChem SID: 46506630; 24891019; 160963542
• PubChem CID: 32326; 21704

理论计算性质

• Acid pKa: 12.454003
• 质子受体: 8
• 质子供体: 4
• LogD (pH = 5.5): -2.2061195
• LogD (pH = 7.4): -2.09263
• Log P: -2.0909638
• 摩尔折射率: 63.1956 cm^3
• 极化性: 24.545797 Å^3
• 极化表面积: 139.54 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

分子性质

理化性质

• 疏水性(logP): -2.115

安全信息

• 保存条件: -20°C
• RTECS编号: AU6200000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 63
• 安全公开号: 36/37
• GHS危险品标识: GHS08
• GHS警示词: Warning
• GHS危险声明: H361
• GHS警示性声明: P281
• 保存温度: -20°C

药理学性质

• 相关基因信息: mouse ... Ahcy(269378)

产品相关信息

• 纯度: ≥99%; ≥99.0% (HPLC); 98%
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C10H13N5O4

详细说明

DrugBank - DB00194

• Drug Groups: approved
• Description: A nucleoside antibiotic isolated from Streptomyces antibioticus. It has some antineoplastic properties and has broad spectrum activity against DNA viruses in cell cultures and significant antiviral activity against infections caused by a variety of viruses such as the herpes viruses, the vaccinia VIRUS and varicella zoster virus. [PubChem]
• Indication: For treatment of chickenpox - varicella, herpes zoster and herpes simplex
• Pharmacology: Vidarabine is a synthetic purine nucleoside analogue with in vitro and in vivo inhibitory activity against herpes simplex virus types 1 (HSV-1), 2 (HSV-2), and varicella-zoster virus (VZV). The inhibitory activity of Vidarabine is highly selective due to its affinity for the enzyme thymidine kinase (TK) encoded by HSV and VZV. This viral enzyme converts Vidarabine into Vidarabine monophosphate, a nucleotide analogue. The monophosphate is further converted into diphosphate by cellular guanylate kinase and into triphosphate by a number of cellular enzymes. in vitro, Vidarabine triphosphate stops replication of herpes viral DNA. When used as a substrate for viral DNA polymerase, Vidarabine triphosphate competitively inhibits dATP leading to the formation of 'faulty' DNA. This is where Vidarabine triphosphate is incorporated into the DNA strand replacing many of the adenosine bases. This results in the prevention of DNA synthesis, as phosphodiester bridges can longer to be built, destabilizing the strand.
• Toxicity: Acute massive overdosage by oral ingestion of the ophthalmic ointment has not occurred. However, the rapid deamination to arabinosylhypoxanthine should preclude any difficulty. The oral LD₅₀ for vidarabine is greater than 5020 mg/kg in mice and rats. No untoward effects should result from ingestion of the entire contents of the tube. Overdosage by ocular instillation is unlikely because any excess should be quickly expelled from the conjunctival sac.
• Affected Organisms: Human Herpes Virus
• Biotransformation: In laboratory animals, vidarabine is rapidly deaminated in the gastrointestinal tract to Ara-Hx.
• Absorption: Systemetic absorption of vidarabine should not be expected to occur following ocular administration and swallowing lacrimal secretions.
• Protein Binding: 24-38%
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1784

Research Area: Infection
Biological Activity:
Vidarabine(Vira-A) is an antiviral drug which is active against herpes simplex and varicella zoster viruses. Vidarabine works by interfering with the synthesis of viral DNA. It is a nucleoside analog, therefore it has to be phosphorylated and to be active. Vidarabine stops replication of herpes viral DNA in 3 ways: 1) competitive inhibition of viral DNA polymerase, 2) incorporation into and termination of the growing viral DNA chain, 3) inactivation of the viral DNA polymerase. [1]

Sigma Aldrich - A5762

Application
Used to study the roles of AMP-activated protein kinase (AMPK) in cell signaling.
Biochem/physiol Actions
Cell-permeable adenylate cyclase inhibitor; in detergent-dispersed rat brain preparation, IC50 = 30 μM. Clinically significant antiviral agent, especially against herpes simplex (HSV),1 by inhibition of DNA polymerase.

Sigma Aldrich - 01832

Biochem/physiol Actions
Cell-permeable adenylate cyclase inhibitor; in detergent-dispersed rat brain preparation, IC50 = 30 μM. Clinically significant antiviral agent, especially against herpes simplex (HSV),1 by inhibition of DNA polymerase.