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Safety Information

01832

Sigma-Aldrich

Adenine 9-β-D-arabinofuranoside

≥99.0% (HPLC)

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:
41106305

Assay

≥99.0% (HPLC)

antibiotic activity spectrum

viruses

Mode of action

DNA synthesis | interferes
enzyme | inhibits

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

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General description

Chemical structure: nucleoside

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.

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Tadashi Terasaka et al.
Journal of medicinal chemistry, 48(15), 4750-4753 (2005-07-22)
From metabolic considerations and prediction of an inhibitor-induced conformational change, novel adenosine deaminase (ADA) inhibitors with improved activities and oral bioavailability have been developed on the basis of our originally designed non-nucleoside ADA inhibitors. They demonstrated in vivo efficacy in
P W Krug et al.
Antimicrobial agents and chemotherapy, 54(1), 452-459 (2009-10-28)
B virus infection of humans results in high morbidity and mortality in as many as 80% of identified cases. The main objective of this study was to conduct a comparative analysis of conventional and experimental antiviral drug susceptibilities of B
Wei Shen et al.
Bioorganic & medicinal chemistry letters, 19(3), 792-796 (2008-12-23)
5'-O-D- and L-amino acid derivatives and 5'-O-(D- and L-amino acid methyl ester phosphoramidate) derivatives of vidarabine (ara-A) were synthesized as vidarabine prodrugs. Some compounds were equi- or more potent in vitro than vidarabine against two pox viruses and their uptake
Larryn W Peterson et al.
Bioorganic & medicinal chemistry letters, 21(13), 4045-4049 (2011-06-07)
We report the synthesis and biological evaluation of Ala-(Val-)l-Ser-CO(2)R prodrugs of 1, where a dipeptide promoiety is conjugated to the P(OH)(2) group of cidofovir (1) via esterification by the Ser side chain hydroxyl group and an ethyl group (4 and
Paul B Yu et al.
Nature chemical biology, 4(1), 33-41 (2007-11-21)
Bone morphogenetic protein (BMP) signals coordinate developmental patterning and have essential physiological roles in mature organisms. Here we describe the first known small-molecule inhibitor of BMP signaling-dorsomorphin, which we identified in a screen for compounds that perturb dorsoventral axis formation
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