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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/REAXYS Number 624881

  •  EC Number 226-893-9

  •  MDL number MFCD00065471

  •  PubChem Substance ID 24891019

  •  NACRES NA.77

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics by Mechanism of Action, Antibiotics  A-F, Antiviral,
Quality Level   100
assay   ≥99%
Mode of action   DNA synthesis | interferes
  enzyme | inhibits
antibiotic activity spectrum   viruses
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

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.

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
AU6200000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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