Structure via PubChem · Public domain (PubChem)
acadesine
Sign in to saveAlso known as AICA-riboside, AR-100, SCH-900395, N(1)-(beta-D-ribofuranosyl)-5-aminoimidazole-4-carboxamide, EC Number 220-097-5, 5-amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide, AIC-Riboside, 5-amino-1-ribofuranosylimidazole-4-carboxamide
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.
Chemical data
- Formula
- C9H14N4O5
- Molecular weight
- 258.23 g/mol
- IUPAC name
- 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide
- SMILES
- C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N)C(=O)N
- InChIKey
- RTRQQBHATOEIAF-UUOKFMHZSA-N
- XLogP
- -2.2
- Polar surface area
- 157 Ų
- H-bond donors
- 5
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- cardiovascular disease, chronic lymphocytic leukemia
via ChEMBL · EBI
Wikidata facts
- Mass
- 258.09642
Show 5 more facts
- chemical formula
- C₉H₁₄N₄O₅
- canonical SMILES
- C1=NC(=C(N1C2C(C(C(O2)CO)O)O)N)C(=O)N
- isomeric SMILES
- C1=NC(=C(N1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)N)C(=O)N
- World Health Organisation international non-proprietary name
- acadesine
- Commons category
- Acadesine
Sources (2)
via Wikidata · CC0
~5 min read
Encyclopedic overview
6 sectionsContents
- Medical uses
- Pharmacology
- Chemistry
- Research
- See also
- References
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.
Excerpted from Wikipedia’s “acadesine” article, available under the CC BY-SA 4.0 licence.