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A5762

Sigma-Aldrich

Adenine 9-β-D-arabinofuranoside

≥99%

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

Quality Level

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)

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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.
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.

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361d

Hazard Classifications

Repr. 2

WGK

WGK 3

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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AMPK regulation of mouse oocyte meiotic resumption in vitro
Chen J, et al.
Developmental Biology, 291(2), 227-238 (2006)
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)
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)
Approved antiviral drugs over the past 50 years
De Clercq E and Li G
Clinical Microbiology Reviews, 29(3), 695-747 (2016)
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)
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