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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

Key Documents

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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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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

signalword

Warning

hcodes

H361d

Hazard Classifications

Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

A5762-10G: + A5762-100MG: + A5762-BULK: + A5762-1G: + A5762-500MG: + A5762-VAR: + A5762-5G:

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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)
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
Approved antiviral drugs over the past 50 years
De Clercq E and Li G
Clinical Microbiology Reviews, 29(3), 695-747 (2016)
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