HYDROXY PENTOXIFYLLINE Chemical Properties

Melting point:

123-125°C

Boiling point:

511.2±56.0 °C(Predicted)

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

Refrigerator

solubility 

DMSO: soluble

form 

solid

pka

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

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

HYDROXY PENTOXIFYLLINE Usage And Synthesis

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.3?Cell permeable.

Chemical Properties

White Solid

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.

Definition

ChEBI: 1-(5-hydroxyhexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione is a dimethylxanthine that is 3,7-dihydro-1H-purine-2,6-dione which is substituted at positions 1,3 and 7 by a 5-hydroxyhexyl group, methyl group and methyl group, respectively. It is a secondary alcohol and a dimethylxanthine.

brand name

ProTec (Cell Therapeutics).

in vitro

(±)-lisofylline is a potent anti-inflammatory agent in which only the (-) optical isomer is biologically active. (±)-lisofylline was found to inhibit the generation of phosphatidic acid from cytokine-activated lysophosphatidic acyl transferase. (±)-lisofylline could also suppress the production of the proinflammatory cytokine ifn-γ, inhibit il-12-mediated stat-4 activation, as well as enhance glucose-stimulated β-cell insulin secretion [1].

in vivo

in a previous study, lisofylline was administered to female non-obese diabetic mice for 3 weeks. cytokines and blood glucose concentrations were monitored. histology and immunohistochemistry were also carried out in pancreatic sections. results showed that lisofylline was able to suppress ifn-γ production, reduce the onset of insulitis and diabetes, and inhibit diabetes [1].

References

[1] ZANDONG YANG  Jerry L N  Meng Chen. Lisofylline: a potential lead for the treatment of diabetes[J]. Biochemical pharmacology, 2005, 69 1: Pages 1-5. DOI:10.1016/j.bcp.2004.08.012
[2] Z-D YANG. The anti-inflammatory compound lisofylline prevents Type I diabetes in non-obese diabetic mice.[J]. Diabetologia, 2002, 45 9: 1307-1314. DOI:10.1007/s00125-002-0901-y
[3] WYSKA E. Pharmacokinetic-pharmacodynamic modeling of methylxanthine derivatives in mice challenged with high-dose lipopolysaccharide.[J]. Pharmacology, 2010, 85 5: 264-271. DOI:10.1159/000288734

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