Compound: ACADESINE
SMILES: O=C(N)c1ncn(c1N)[C@@H]2O[C@H](CO)[C@H]([C@H]2O)O
InChIKey: RTRQQBHATOEIAF-UUOKFMHZSA-N
Synonyms: ACADESINE, 2627-69-2, AICA-riboside, Arasine, Acadesina, AICA riboside, AIC-Riboside, Acadesinum, GP-1-110, Protara, 5-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide, NSC-105823, DTXSID5046015, GP 1-110, 5-Amino-4-imidazolecarboxamide ribofuranoside, 5-Aminoimidazole-4-carboxamide ribonucleoside, 53IEF47846, 5-Aminoimidazole-4-carboxamide riboside, 5-Amino-1-beta-ribofuranosyl-imidazole-4-carboxamide, 5-Amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide, 5-Amino-1beta-D-ribofuranosylimidazole-4-carboxyamide, 5-aminoimidazole-4-carboxamide-1-beta-D-ribofuranoside, DTXCID3026015, CHEBI:28498, NSC105823, 5-Amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazole-4-carboxamide, 1H-Imidazole-4-carboxamide, 5-amino-1-beta-D-ribofuranosyl-, Z-Riboside, 5-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1H-imidazole-4-carboxamide, AICA ribofuranoside, AICA ribonucleoside, aminoimidazole carboxamide ribonucleoside, RefChem:551450, ARA100, ARA-100, C01EB13, 1-ribosyl-4-carboxamido-5-aminoimidazole, 220-097-5, 5-Amino-1-beta-D-ribofuranosyl-1H-imidazole-4-carboxamide, MFCD00869751, AICAR (Acadesine), C9H14N4O5, 5-amino-1-(beta-D-ribofuranosyl)-1H-imidazole-4-carboxamide, SCH-900395, 1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl-, 5-amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-imidazole-4-carboxamide, 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]imidazole-4-carboxamide, 5-Amino-1-.beta.-D-ribofuranosylimidazole-4-carboxamide, Acadra, NSC 105823, SMR003435998, CAS-2627-69-2, Acadesinum [INN-Latin], 5-Aminoimidazole-4-carboxamide-1-?-D-ribofuranoside, Acadesina [INN-Spanish], Acadesine [USAN:INN:BAN], UNII-53IEF47846, ATH-001, 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide, NCGC00096051-02, EINECS 220-097-5, AICAR (Standard), Acadesine (AICAR), AICAR (Acadesine)?, ath001, ACADESINE [INN], ACADESINE [MI], Acadesine (USAN/INN), ACADESINE [USAN], Inosine Unknow impurity 4, ACADESINE [MART.], ACADESINE [WHO-DD], 5-Amino-1-.beta.-D-ribofuranosyl-1H-imidazole-4-carboxamide, MLS004774120, MLS006010069, SCHEMBL219336, GTPL5133, orb1308527, CHEMBL1551724, EC Number 220-097-5, Imidazole-4-carboxamide, 5-amino-1-beta-D-ribofuranosyl-, AICA-riboside; LC-tDDA; CE40, EX-A7096, MSK10569, Tox21_111551, HB2152, HSCI1_000213, HY-13417R, NSC811018, s1802, AICAR, >=98% (HPLC), powder, AKOS016004462, Tox21_111551_1, CCG-267038, CS-1951, DB04944, NA03552, NSC-811018, 5-Amino-4-imidazolecarboxamide Riboside, SRI-4077-02, SRI-4077_04, NCGC00165736-01, NCGC00165736-03, NCGC00165736-04, NCGC00165736-16, AC-26840, AS-13787, HY-13417, GP-1-110-0, NS00014782, 5-amino-1-ribofuranosylimidazole-4-carboxamide, C04663, D02742, 5-Aminoimidazole-4-carboxamide-1-b-D-ribofuranose, 5-Amino-1-beta-ribofuranosylimidazole-4-carboxamide, Q4671562, BRD-K53448858-001-07-0, N1-(b-D-Ribofuranosyl)-5-aminoimidazole-4-carboxamide, 5-AMINO-1-B-D-RIBOFURANOSYLIMIDAZOLE-4-CARBOXAMIDE, 5-Aminoimidazole-4-carboxamide 1-(1/4)?-D-ribofuranoside, N(1)-(beta-D-ribofuranosyl)-5-aminoimidazole-4-carboxamide, 5-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-.BETA.-D-RIBOFURANOSIDE
Theoretical properties:
molecular_formula: C9H14N4O5
molecular_weight: 258.23 g/mol
exact_mass: 258.09641956 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 7
rotatable_bond_count: 3
heavy_atom_count: 18
topological_polar_surface_area: 157 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Acadesine is 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. It has a role as an antineoplastic agent and a platelet aggregation inhibitor. It is an aminoimidazole, a 1-ribosylimidazolecarboxamide and a nucleoside analogue.
chebi: 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.
chembl: ACADESINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Acadesine (INN), also known as 5-aminoimidazole-4-carboxamide-1-β-D-ribofuranoside, AICA-riboside, and AICAR, is an AMP-activated protein kinase activator which is used for the treatment of acute lymphoblastic leukemia and may have applications in treating other disorders such as diabetes. Acadesine 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.
Acadesine is an adenosine regulating agent developed by PeriCor Therapeutics and licensed to Schering-Plough in 2007 for phase III studies. The drug is a potential first-in-class agent for prevention of reperfusion injury in CABG surgery. Schering began patient enrollment in phase III studies in May 2009. The trial was terminated in late 2010 based on an interim futility analysis.