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  • A5762 - Adenine 9-β-D-arabinofuranoside

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A5762 Sigma-Aldrich

Adenine 9-β-D-arabinofuranoside

≥99%

Synonym: 9-β-D-Arabinofuranosyladenine, Ara-A, Vidarabine

  • CAS Number 5536-17-4

  • Empirical Formula (Hill Notation) C10H13N5O4

  • Molecular Weight 267.24

  •  Beilstein Registry Number 624881

  •  EC Number 226-893-9

  •  MDL number MFCD00065471

  •  PubChem Substance ID 24891019

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics by Mechanism of Action, Antiviral, Biochemicals and Reagents,
InChI Key   OIRDTQYFTABQOQ-UHTZMRCNSA-N
assay   ≥99%
Mode of action   DNA synthesis | interferes
  enzyme | inhibits
antibiotic activity spectrum   viruses
storage temp.   −20°C
Gene Information   mouse ... Ahcy(269378)

Description

Application

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.

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.

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
AU6200000

Documents

Certificate of Analysis

Certificate of Origin

Protocols & Articles
Peer-Reviewed Papers
15

References

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