AMZ

AMINOIMIDAZOLE 4-CARBOXAMIDE RIBONUCLEOTIDE


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Chemical Component Summary

NameAMINOIMIDAZOLE 4-CARBOXAMIDE RIBONUCLEOTIDE
SynonymsAICAR
Identifiers[(2R,3S,4R,5R)-5-(5-amino-4-aminocarbonyl-imidazol-1-yl)-3,4-dihydroxy-oxolan-2-yl]methyl dihydrogen phosphate
FormulaC9 H15 N4 O8 P
Molecular Weight338.211
TypeNON-POLYMER
Isomeric SMILESc1nc(c(n1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)N)C(=O)N
InChIInChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
InChIKeyNOTGFIUVDGNKRI-UUOKFMHZSA-N

Chemical Details

Formal Charge0
Atom Count37
Chiral Atom Count4
Bond Count38
Aromatic Bond Count5

Drug Info: DrugBank

DrugBank IDDB01700 
NameAICA ribonucleotide
Groups
  • investigational
  • experimental
Description5-Aminoimidazole-4-carboxamide ribonucleotide (AICAR) is an intermediate in the generation of inosine monophosphate and analog of adenosine monophosphate (AMP) that is capable of stimulating AMP-dependent protein kinase (AMPK) activity. AICAR has been used clinically to treat and protect against cardiac ischemic injury. The drug was first used in the 1980s as a method to preserve blood flow to the heart during surgery and is currently of interest as a potential treatment for diabetes by increasing the metabolic activity of tissues by changing the physical composition of muscle.
Synonyms
  • 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
  • 1-(5'-phosphoribosyl)-5-amino-4-imidazolecarboxamide
  • AICA ribonucleotide
  • 5-phosphoribosyl-4-carbamoyl-5-aminoimidazole
  • AICA-ribonucleotide
Categories
  • Blood Glucose Lowering Agents
  • Imidazoles
  • Nucleic Acids, Nucleotides, and Nucleosides
  • Nucleotides
CAS number3031-94-5

Drug Targets

NameTarget SequencePharmacological ActionActions
Bifunctional purine biosynthesis protein PURHMAPGQLALFSVSDKTGLVEFARNLTALGLNLVASGGTAKALRDAGLAVRD...unknown
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 65110
ChEMBL CHEMBL483849
ChEBI CHEBI:18406