(+/-)-Lisofylline
LISOFYLLINE · 1-(5-hydroxyhexyl)-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione · (±)-Lisofylline · (+/-)-LISOFYLLINE · Penthydroxifillyne · Lisofylline (racemic) · Hydroxy pentoxifylline · 5-Hydroxy pentoxifylline
Identifiers & Physical Properties
| CAS No. | 100324-81-0 |
|---|---|
| Molecular formula | C13H20N4O3 |
| Average molar mass | 280.32 g/mol |
| Monoisotopic mass | 280.15354051 g/mol |
| SMILES | CC(O)CCCCn1c(=O)c2c(ncn2C)n(C)c1=O |
| InChIKey | NSMXQKNUPPXBRG-UHFFFAOYSA-N |
| PubChem CID | 57782 |
| ChEMBL | CHEMBL1514176 |
| ChEBI | CHEBI:143565 |
| DTXSID | DTXSID6046343 |
Chemical & Physical Properties
| XLogP | 0.7 |
|---|---|
| Topological polar surface area | 78.7 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 4 |
| Rotatable bonds | 5 |
| Heavy atoms | 20 |
| Formal charge | 0 |
| Complexity | 390 |
| Drugs | Pharmaceuticals -> Metabolite of Pentoxifylline |
| Melting point | 123-125°C |
| Boiling point | 511.2±56.0 °C(Predicted) |
| Density | 1.32±0.1 g/cm3(Predicted) |
| Storage conditions | Refrigerator |
| Solubility | DMSO: soluble |
| Physical state | solid |
| pKa (acidity coefficient) | 15.22±0.20(Predicted) |
| Color | white |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months. |
| InChI | InChI=1S/C13H20N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8-9,18H,4-7H2,1-3H3 |
| InChIKey | NSMXQKNUPPXBRG-UHFFFAOYSA-N |
| SMILES | N1(C)C2=C(N(C)C(=O)N(CCCCC(O)C)C2=O)N=C1 |
| NCI Dictionary of Cancer Terms | lisofylline |
| FDA UNII | R99EE080JS |
| Water hazard class (WGK) | 3 |
Safety & Regulations
| Water hazard class (WGK) | 3 |
|---|
Applications & Uses
Description
Lisofylline (6493-06-7, racemic) displays anti-inflammatory activity. Regulates immune cell function and autoimmune response by inhibition of IL-12 signalling and cytokine production.1 Protects pancreatic beta cells and prevents type I diabetes in non-obese diabetic mice.2 Lisofylline reduces LPS-induced TNF alpha levels in CD-1 mice.3Cell permeable.
Uses
A major oxidative metabolite of Pentoxifylline. A potent inhibitor of phosphatidic acid generation (IC50=0.6uM). Protects mice from endotoxic shock and attenuates sepsis-induced acute lung injury in pig.