AMZ

AMINOIMIDAZOLE 4-CARBOXAMIDE RIBONUCLEOTIDE

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is present as a standalone ligand in 22 entries

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Chemical Component Summary
Name	AMINOIMIDAZOLE 4-CARBOXAMIDE RIBONUCLEOTIDE
Synonyms	AICAR
Identifiers	[(2R,3S,4R,5R)-5-(5-amino-4-aminocarbonyl-imidazol-1-yl)-3,4-dihydroxy-oxolan-2-yl]methyl dihydrogen phosphate
Formula	C₉ H₁₅ N₄ O₈ P
Molecular Weight	338.211
Type	NON-POLYMER
Isomeric SMILES	c1nc(c(n1[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)N)C(=O)N
InChI	InChI=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
InChIKey	NOTGFIUVDGNKRI-UUOKFMHZSA-N

Chemical Details
Formal Charge	0
Atom Count	37
Chiral Atom Count	4
Bond Count	38
Aromatic Bond Count	5

Drug Info: DrugBank

DrugBank ID	DB01700
Name	AICA ribonucleotide
Groups	investigational experimental
Description	5-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	AICA ribonucleotide 5-phosphoribosyl-4-carbamoyl-5-aminoimidazole AICAR 5-aminoimidazole-4-carboxamide ribotide acadesine 5'-monophosphate 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide 5'-phospho-ribosyl-5-amino-4-imidazole carboxamide AICA-ribonucleotide 1-(5'-phosphoribosyl)-5-amino-4-imidazolecarboxamide 5'-phosphoribosyl-5-amino-4-imidazolecarboxamide
Categories	Blood Glucose Lowering Agents Imidazoles Nucleic Acids, Nucleotides, and Nucleosides Nucleotides
CAS number	3031-94-5

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Bifunctional purine biosynthesis protein PURH	MAPGQLALFSVSDKTGLVEFARNLTALGLNLVASGGTAKALRDAGLAVRD...	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