A5762

Adenine 9-β-D-arabinofuranoside

≥99%

• Synonym(s): 9-β-D-Arabinofuranosyladenine, Ara-A, Vidarabine
• Empirical Formula (Hill Notation): C₁₀H₁₃N₅O₄
• CAS Number: 5536-17-4
• Molecular Weight: 267.24
• UNSPSC Code: 12352202
• NACRES: NA.77
• PubChem Substance ID: 24891019
• EC Number: 226-893-9
• Beilstein/REAXYS Number: 624881
• MDL number: MFCD00065471

Properties

• Quality Segment: 100
• assay: ≥99%
• form: powder
• antibiotic activity spectrum: viruses
• mode of action: DNA synthesis | interferes, enzyme | inhibits
• storage temp.: −20°C
• SMILES string: Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O
• 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
• InChI key: OIRDTQYFTABQOQ-UHTZMRCNSA-N
• Gene Information: mouse ... Ahcy(269378)

Description

General description

Adenine 9-β-D-arabinofuranoside (AraA) is a nucleoside analog. It is an antiviral drug and targets viral DNA polymerases and is majorly used for treating herpes simplex viral infection. It is a potent inhibitor of AMP-activated protein kinase (AMPK). It also inhibits cardiac type 5 adenylyl cyclase but does not improve pathology in cardiovascular diseases.

Application

Used to study the roles of AMP-activated protein kinase (AMPK) in cell signaling.

Adenine 9-β-D-arabinofuranoside has been used for the inhibition of 5′ AMP-activated protein kinase (AMPK) in liver, muscle and cardiac cells H9c2.

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), by inhibition of DNA polymerase.

Cell-permeable adenylyl cyclase inhibitor. IC₅₀ = 30 μM in detergent-dispersed rat brain preparation.

Safety Information

• Pictograms: GHS08
• Signal Word: Warning
• Hazard Codes: H361d
• Precautionary Statements: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Repr. 2
• Storage Class: 11 - Combustible Solids
• WGK: WGK 3