CHEBI:28498 - acadesine

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ChEBI Name acadesine
ChEBI ID CHEBI:28498
Definition A 1-ribosylimidazolecarboxamide in which the carboxamide group is situated at position 4 of the imidazole ring, which is further substituted at position 5 by an amino group. A purine nucleoside analogue and activator of AMP-activated protein kinase, it is is used for the treatment of acute lymphoblastic leukemia and is reported to have cardioprotective effects.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:2025, CHEBI:20539
Supplier Information No supplier information found for this compound.
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Formula C9H14N4O5
Net Charge 0
Average Mass 258.23130
Monoisotopic Mass 258.09642
InChI InChI=1S/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m1/s1
InChIKey RTRQQBHATOEIAF-UUOKFMHZSA-N
SMILES NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N
Roles Classification
Application(s): platelet aggregation inhibitor
A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing acadesine (CHEBI:28498) has role antineoplastic agent (CHEBI:35610)
acadesine (CHEBI:28498) has role platelet aggregation inhibitor (CHEBI:50427)
acadesine (CHEBI:28498) is a 1-ribosylimidazolecarboxamide (CHEBI:26556)
acadesine (CHEBI:28498) is a aminoimidazole (CHEBI:22512)
acadesine (CHEBI:28498) is a nucleoside analogue (CHEBI:60783)
Incoming AICA ribonucleotide (CHEBI:18406) has functional parent acadesine (CHEBI:28498)
IUPAC Name
5-amino-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxamide
INNs Sources
acadesina WHO MedNet
acadésine WHO MedNet
acadesine WHO MedNet
acadesinum WHO MedNet
Synonyms Sources
5-amino-1-β-D-ribofuranosyl-4-imidazolecarboxamide ChemIDplus
5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide ChemIDplus
5-amino-1-β-ribofuranosyl-imidazole-4-carboxamide ChemIDplus
5-amino-1-ribofuranosylimidazole-4-carboxamide ChEBI
5-amino-1β-D-ribofuranosylimidazole-4-carboxyamide ChemIDplus
5-amino-4-imidazolecarboxamide ribofuranoside ChemIDplus
5-aminoimidazole-4-carboxamide ribonucleoside ChemIDplus
AIC-Riboside ChemIDplus
AICA-riboside ChemIDplus
AICAr
Note: (2014-05-21) Note that this synonym is case sensitive: AICAr is used to refer to the nucleoside (with a hydroxy group at the 5' position) while AICAR refers to the corresponding nucleotide (i.e. the corresponding 5'-phosphate).
 ChEBI
EC Number 220-097-5 ChEBI
GP 1-110 ChemIDplus
GP-1-110 ChemIDplus
N1-(β-D-ribofuranosyl)-5-aminoimidazole-4-carboxamide ChEBI
Manual Xrefs Databases
37 DrugCentral
Acadesine Wikipedia
D02742 KEGG DRUG
DB04944 DrugBank
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Registry Numbers Types Sources
2627-69-2 CAS Registry Number KEGG DRUG
2627-69-2 CAS Registry Number ChemIDplus
38255 Reaxys Registry Number Reaxys
Citations Types Sources
17513706 PubMed citation Europe PMC
17706943 PubMed citation Europe PMC
18090925 PubMed citation Europe PMC
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24519895 PubMed citation Europe PMC
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Last Modified
22 February 2017