Compound: (R)-Lisofylline
SMILES: O=c1n(c(=O)c2n(C)cnc2n1C)CCCC[C@H](O)C
InChIKey: NSMXQKNUPPXBRG-SECBINFHSA-N
Synonyms: (R)-Lisofylline, LISOFYLLINE, 100324-81-0, ProTec, Lisophylline, CT-1501R, lisofilina, CT 1501R, (R)-Lisophylline, Lisofylline, (r)-, lisofyllinum, 1-[(5R)-5-hydroxyhexyl]-3,7-dimethylpurine-2,6-dione, CT1501R, 1-[(R)-5-hydroxyhexyl]theobromine, DTXSID7058709, CHEBI:143527, L1F2Q2X956, 1-((R)-5-Hydroxyhexyl)theobromine, 1-(5R-Hydroxyhexyl)-3,7-dimethylxanthine, 1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione, 1-((5R)-5-hydroxyhexyl)-3,7-dimethylpurine-2,6-dione, Lisofenicol, 1-((5R)-5-hydroxyhexyl)-3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione, 3,7-Dimethyl-1-(5-hydroxyhexyl)xanthine, 1-(5'-Hydroxyhexyl)-3,7-dimethylxanthine, RefChem:799370, 1H-Purine-2,6-dione, 3,7-dihydro-1-(5-hydroxyhexyl)-3,7-dimethyl-, DTXCID70820015, (R)-1-(5-Hydroxyhexyl)-3,7-dimethyl-1H-purine-2,6(3H,7H)-dione, 1H-Purine-2,6-dione, 3,7-dihydro-1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl-, 3,7-Dihydro-1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl-1H-purine-2,6-dione, 1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl-purine-2,6-dione, 1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione, (-)-lisofylline, ProTec (TN), LISOFYLLINE [MI], LISOFYLLINE [INN], Lisofylline (USAN/INN), LISOFYLLINE [USAN], CHEMBL1411, SCHEMBL39131, (R)-LSF, LISOFYLLINE [WHO-DD], GTPL9225, orb1306234, 1H-Purine-2,6-dione, 3,7-dihydro-1-(5-hydroxyhexyl)-3,7-dimethyl-, (R)-, EX-A6722, LSF, MFCD00867573, AKOS025394050, DB12406, FL24911, HY-109854A, NCGC00186630-01, DA-54953, MS-23979, 1-(5-R-hydroxyhexyl)-3,7-dimethylxanthine, CS-0034091, NS00068764, R-1-(5-Hydroxyhexyl)-3,7-dimethylxanthine, 1-(5'-R-Hydroxyhexyl)-3,7-dimethylxanthine, (r)-1-(5-hydroxyhexyl)-3,7-dimethylxanthine, D04748, G12758, Q15409404
Theoretical properties:
molecular_formula: C13H20N4O3
molecular_weight: 280.32 g/mol
exact_mass: 280.15354051 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 5
heavy_atom_count: 20
topological_polar_surface_area: 78.7 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: (R)-lisofylline is a 1-(5-hydroxyhexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione that has (R)-configuration. A synthetic small molecule which was under development for the treatment of type 1 diabetes mellitus. It has a role as an immunomodulator and an anti-inflammatory agent. It is an enantiomer of a (S)-lisofylline.
chebi: A 1-(5-hydroxyhexyl)-3,7-dimethyl-3,7-dihydro-1<em>H</em>-purine-2,6-dione that has (<i>R</i>)-configuration. A synthetic small molecule which was under development for the treatment of type 1 diabetes mellitus.
chembl: LISOFYLLINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.
wikipedia: Lisofylline (LSF) is a synthetic small molecule with novel anti-inflammatory properties. LSF can effectively prevent type 1 diabetes in preclinical models and improves the function and viability of isolated or transplanted pancreatic islets.  It is a metabolite of pentoxifylline.
As well, LSF improves cellular mitochondrial function and blocks interleukin-12 (IL-12) signaling and STAT-4 activation in target cells and tissues. IL-12 and STAT-4 activation are important pathways linked to inflammation and autoimmune damage to insulin producing cells. Therefore, LSF and related analogs could provide a new therapeutic approach to prevent or reverse type 1 diabetes. LSF also directly reduces glucose-induced changes in human kidney cells suggesting that LSF and analogs have the potential to treat the complications associated with diabetes.