Acadesine
AAKG · AMPK · ACADESINE · AMPK1 · Acair · PRKAB1 · AMPKa1 · Acadesine, AICA
Identifiers & Physical Properties
| CAS No. | 2627-69-2 |
|---|---|
| Molecular formula | C9H14N4O5 |
| Average molar mass | 258.23 g/mol |
| Monoisotopic mass | 258.09641955 g/mol |
| SMILES | NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N |
| InChIKey | RTRQQBHATOEIAF-UUOKFMHZSA-N |
| PubChem CID | 17513 |
| ChEMBL | CHEMBL1551724 |
| ChEBI | CHEBI:28498 |
| EC No. | 220-097-5 |
| DTXSID | DTXSID5046015 |
Chemical & Physical Properties
| XLogP | -2.2 |
|---|---|
| Topological polar surface area | 157 |
| Hydrogen bond donors | 5 |
| Hydrogen bond acceptors | 7 |
| Rotatable bonds | 3 |
| Heavy atoms | 18 |
| Formal charge | 0 |
| Complexity | 330 |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| Collision Cross Section | 170.4 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]152 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine]153.55 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]153 Ų [M+H]+ [CCS Type: TW |
| Melting point | 214-215 °C |
| Boiling point | 726.3±60.0 °C(Predicted) |
| Density | 2.06±0.1 g/cm3(Predicted) |
| Storage conditions | -20°C |
| Solubility | H2O: >10 mg/mLSoluble in DMSO at 2mg/ml. Soluble in water or ethanol at less than 1mg/ml |
| Physical state | powder |
| pKa (acidity coefficient) | 13.27±0.70(Predicted) |
| Color | tan |
| Biological source | rabbit |
| λmax | 265nm(NaOH)(lit.) |
| Merck | 14,16 |
| Specific Activity | 255-345nmol/min·mg |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20°C for up to 3 months. |
| InChI | 1S/C9H14N4O5/c10-7-4(8(11)17)12-2-13(7)9-6(16)5(15)3(1-14)18-9/h2-3,5-6,9,14-16H,1,10H2,(H2,11,17)/t3-,5-,6-,9-/m1/s1 |
| InChIKey | RTRQQBHATOEIAF-UUOKFMHZSA-N |
| SMILES | NC(=O)c1ncn([C@@H]2O[C@H](CO)[C@@H](O)[C@H]2O)c1N |
| CAS DataBase Reference | 2627-69-2(CAS DataBase Reference) |
| FDA UNII | F0X88YW0YK |
| NCI Drug Dictionary | acadesine |
| ATC code | C01EB13 |
| EPA Substance Registry System | 1H-Imidazole-4-carboxamide, 5-amino-1-.beta.-D-ribofuranosyl- (2627-69-2) |
| UNSPSC Code | 12352203 |
| NACRES | NA.77 |
| GHS pictogram | GHS07,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H315-H319-H360D |
| GHS precautionary statements | P202-P264-P280-P302+P352-P305+P351+P338-P308+P313 |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Hazard symbols | Xi,T |
| Risk statements (R) | 36/37/38-61 |
| Safety statements (S) | 26-36-45-53 |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29349990 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 4.4% (2 of 45) of reports.WarningH315 (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 Classes and Categories | Skin Irrit. 2 (93.3%) |
| Personal protective equipment (PPE) | dust mask type N95 (US), Eyeshields, Gloves |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| Customs code | 29349990 |
| Risk statements (R) | 36/37/38-61 |
| Signal word | Danger |
| GHS pictogram | GHS07,GHS08 |
| Hazard symbols | Xi,T |
| Safety statements (S) | 26-36-45-53 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H315-H319-H360D |
| GHS precautionary statements | P202-P264-P280-P302+P352-P305+P351+P338-P308+P313 |
Applications & Uses
Description
AICAR (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.
Uses
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.
Uses
glucose uptake stimulant; AMPK activator
Uses
5-Aminoimidazole-4-carboxamide 1-beta-D-ribofuranoside is used as a cell permeable activator of AMP-activated protein kinase (AMPK), a metabolic master regulator that is activated in times of reduced energy availability (high cellular AMP:ATP ratios) and serves to inhibit anabolic processes. In vivo, pharmacologic activation of AMPK with AICAR mimics exercise and triggers insulin-independent glucose uptake by skeletal muscle.
General Description
Adenosine monophosphateprotein kinase (AMPK) activator 5-aminoimidazole-4-carboxamideribonucleotide(AICAR)modulates cellular energy. It regulates lipid and glucose metabolism, pro-inflammatory responses,cytokine production,cell proliferation and apoptosis. AICAR improves ischemia or reperfusion injury and kidney fibrosis in rats. It provides protection against acute tubular necrosis.