Adenine 9-β-D-arabinofuranoside

SIGMA/A5762 - ≥99%

Synonym: 9-β-D-Arabinofuranosyladenine; Ara-A; Vidarabine

CAS Number: 5536-17-4
Empirical Formula (Hill Notation): C₁₀H₁₃N₅O₄
Molecular Weight: 267.24
EC Number: 226-893-9
MDL Number: MFCD00065471
Linear Formula: C₁₀H₁₃N₅O₄
Product Type: Chemical

Catalog Number	PKG Qty.	Price	Quantity


45-A5762-1G	1 g	$354.00 1/EA		Add To Favorites

Properties
Descriptions
Safety Info.
Basic Data

antibiotic activity spectrum	viruses
assay	≥99%
form	powder
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
mode of action	DNA synthesis \| interferes
	enzyme \| inhibits
Quality Level	100
SMILES string	Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O
storage temp.	−20°C

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.
Application:	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.
Biochem/physiol Actions:	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.

Symbol	GHS08
Signal word	Warning
Hazard statements	H361
Precautionary statements	P201 - P202 - P280 - P308 + P313 - P405 - P501
Hazard Codes	Xn
Risk Statements	63
Safety Statements	36/37
RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥99%
Storage Temp.	−20°C
UNSPSC	12352202

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