Basic information
- CAS
2627-69-2- Standard SMILES
NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N- InChIKey
RTRQQBHATOEIAF-UUOKFMHZSA-N- Molecular formula
- C9H14N4O5
- Average molar mass
- 258.23 g/mol
- Monoisotopic mass
- 258.09641955
Overview
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.
Names & identifiers
- Preferred name
- Acadesine
- IUPAC
- 5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carboxamide
- English name
- AICAR
- Molecular formula
- C9H14N4O5
- Molecular weight
- 258.23
Names & synonyms
ACADESINE2627-69-2AICA-ribosideArasineAICA ribosideAcadesinaAIC-RibosideAcadesinumGP-1-110ProtaraDTXSID50460155-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide
Show more names
AAKGAMPKAMPK1AcairPRKAB1AMPKa1Acadesine, AICA
NSC-105823GP 1-1105-Amino-4-imidazolecarboxamide ribofuranoside5-Aminoimidazole-4-carboxamide ribonucleoside53IEF478465-Aminoimidazole-4-carboxamide riboside5-Amino-1-beta-ribofuranosyl-imidazole-4-carboxamide5-Amino-1-beta-D-ribofuranosyl-4-imidazolecarboxamide
Database identifiers
- CAS
2627-69-2- PubChem CID
- 17513
- DTXSID
DTXSID5046015- ChEMBL
CHEMBL1551724- ChEBI
CHEBI:28498- UNII
- 53IEF47846
- EC Number
- 220-097-5
- Nikkaji
- J14.878D
Properties
Computed structural properties
- XLogP
- -2.2
- Topological polar surface area
- 157 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 330
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Collision Cross Section
170.4 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]
152 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]
153.55 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
153 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 214 · 214-215 °C
- Boiling point
- 726.3 · 726.3±60.0 °C(Predicted)
- Density
- 2.06 · 2.06±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 2 O: · H2O: >10 mg/mL
- form
- powder
- pka
- 13.27 · 13.27±0.70(Predicted)
- color
- tan
- biological source
- rabbit
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 4.4% (2 of 45) of reports.
Warning
H315 (93.3%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (93.3%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29349990
- risk_code
- 36/37/38-61
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- hazard_code
- Xi,T
- safety_code
- 26-36-45-53
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H360D
- Precautionary statements
- P202-P264-P280-P302+P352-P305+P351+P338-P308+P313
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein BindingNegligible (approximately 1%)
Pharmacodynamics
Acadesine has been shown to induce cell death apoptosis selectively in B-cells taken from healthy subjects and patients with B-CLL, with little effect on T-cells. As T-cells have an important role in fighting infection, it is anticipated that patients treated with acadesine will have a reduced risk of serious infections compared to those on current chemotherapies.
Mechanism of Action
The mechanism by which acadesine selectively kills B-cells is not yet fully elucidated. The action of acadesine does not require the tumour suppressor protein p53 like other treatments. This is important, as p53 is often missing or defective in cancerous B-cells. Studies have shown acadesine activates AMPK and induces apoptosis in B-cell chronic lymphocytic leukemia cells but not in T lymphocytes.
Biological Half-Life1 week
Uses & manufacturing
General Manufacturing Information1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl-: ACTIVE
Applications
DescriptionAICAR (2627-69-2) activates AMP-activated protein kinase (AMPK). Promotes ligand-independent activation of the insulin receptor.1 Promotes skeletal muscle autophagy via activation of FoxO3a.2 Controls smooth muscle cell hyperproliferation in vascular disease.3 Induces osteogenic differentiation in mesenchymal stem cells.4 Inhibits proinflammatory response in glial cells.5 Cell permeable.
AICAR is a nucleoside analogue that is able to enter nucleoside pools and is able to significantly increase levels of adenosine during periods of ATP breakdown. Adenosine-regulating agents (ARAs) hav e been recognized for therapeutic potential in myocardial ischemia. Cardioprotective.
Related reactions
12 records
Compound notes
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