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

• ChemBase ID: 79
• Molecular Formular: C10H13N5O4
• Molecular Mass: 267.24132
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R)-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: armes
• Brand Name: Arasena-A; Spongoadenosine; Vira-A; Vidarabin
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 12.454003
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.2061195
• LogD (pH = 7.4): -2.09263
• Log P: -2.0909638
• Molar Refractivity: 63.1956 cm^3
• Polarizability: 24.545797 Å^3
• Polar Surface Area: 139.54 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Hydrophobicity(logP): -2.115

Safety Information

• Storage Condition: -20°C
• RTECS: AU6200000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63
• Safety Statements: 36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H361
• GHS Precautionary statements: P281
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: mouse ... Ahcy(269378)

Product Information

• Purity: ≥99%; ≥99.0% (HPLC); 98%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C10H13N5O4

DETAILS

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.