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Merck

A5762

Adenine 9-β-D-arabinofuranoside

≥99%

Synonym(s):

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

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About This Item

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

Product Name

Adenine 9-β-D-arabinofuranoside, ≥99%

InChI key

OIRDTQYFTABQOQ-UHTZMRCNSA-N

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

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O

assay

≥99%

form

powder

antibiotic activity spectrum

viruses

mode of action

DNA synthesis | interferes
enzyme | inhibits

storage temp.

−20°C

Quality Level

100

Gene Information

mouse ... Ahcy(269378)

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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.
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), by inhibition of DNA polymerase.
Cell-permeable adenylyl cyclase inhibitor. IC50 = 30 μM in detergent-dispersed rat brain preparation.

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.

pictograms

Health hazard
GHS08

signalword

Warning

hcodes

H361d

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
BCCF0177
BCBV1348
BCBQ0660V
BCBQ0660
BCBL6590V

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AMPK regulation of mouse oocyte meiotic resumption in vitro
Chen J, et al.
Developmental Biology, 291(2), 227-238 (2006)
The direct effect of leptin on skeletal muscle thermogenesis is mediated by substrate cycling between de novo lipogenesis and lipid oxidation
Solinas G, et al.
Febs Letters, 577(3), 539-544 (2004)
GYY4137, a novel hydrogen sulfide-releasing molecule, likely protects against high glucose-induced cytotoxicity by activation of the AMPK/mTOR signal pathway in H9c2 cells
Wei W, et al.
Molecular and Cellular Biochemistry, 389(1-2), 249-256 (2014)
Antiviral drug vidarabine possessing cardiac type 5 adenylyl cyclase inhibitory property did not affect cardiohemodynamic or electrophysiological variables in the halothane-anesthetized dogs
Wada T, et al.
The Journal of Toxicological Sciences, 41(1), 115-122 (2016)
AMPK involvement in endoplasmic reticulum stress and autophagy modulation after fatty liver graft preservation: a role for melatonin and trimetazidine cocktail
Zaouali MA, et al.
Journal of Pineal Research, 55(1), 65-78 (2013)
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