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Merck
CN

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
Beilstein:
624881
EC Number:
226-893-9
MDL number:
MFCD00065471
UNSPSC Code:
12352202
PubChem Substance ID:
24891019
NACRES:
NA.77

Key Documents

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

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H361d

Hazard Classifications

Repr. 2

Storage Class Code

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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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)
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)
AMPK regulation of mouse oocyte meiotic resumption in vitro
Chen J, et al.
Developmental Biology, 291(2), 227-238 (2006)
Approved antiviral drugs over the past 50 years
De Clercq E and Li G
Clinical Microbiology Reviews, 29(3), 695-747 (2016)
Arnon P Kater et al.
Leukemia research, 38(1), 34-41 (2013-11-19)
Resistance to chemotherapy-induced apoptosis in CLL is associated with overexpression of antiapoptotic proteins induced by signals from the microenvironment. In vitro, dasatinib effectively inhibits expression of anti-apoptotic regulators and restores fludarabine sensitivity in activated CLL. The aim of this study
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