ChemicalBook--->CAS DataBase List--->6493-06-7

6493-06-7

6493-06-7 Structure

6493-06-7 Structure
IdentificationBack Directory
[Name]

HYDROXY PENTOXIFYLLINE
[CAS]

6493-06-7
[Synonyms]

LISOFYLLINE
(+/-)-LISOFYLLINE
Penthydroxifillyne
Lisofylline (racemic)
HYDROXY PENTOXIFYLLINE
5-Hydroxy pentoxifylline
pentoxyfylline metabolite 2
Hydroxy Pentoxifylline (rac-Lisofylline)
3,7-Dihydro-1-(5-hydroxyhexyl)-3,7-diMethyl-
(+/-)-1-(5-HYDROXYHEXYL)-3,7-DIMETHYLXANTHINE
Pentoxifylline Impurity 16 ((+/-)-Lisofylline)
1H-Purine-2,6-dione, 3,7-dihydro-1-(5-hydroxyhexyl)-3,7-dimethyl-
1-(5-hydroxyhexyl)-3,7-dimethylxanthine, pentoxyfylline metabolite 2
1-(5-Hydroxyhexyl)-3,7-dimethyl-1,2,3,6-tetrahydro-7H-purine-2,6-dione
1-(5-hydroxyhexyl)-3,7-dimethylxanthine, pentoxyfylline metabolite 2/(±)-Lisofylline
Hydroxy PentoxifyllineQ: What is Hydroxy Pentoxifylline Q: What is the CAS Number of Hydroxy Pentoxifylline Q: What is the storage condition of Hydroxy Pentoxifylline Q: What are the applications of Hydroxy Pentoxifylline
[Molecular Formula]

C13H20N4O3
[MDL Number]

MFCD00867573
[MOL File]

6493-06-7.mol
[Molecular Weight]

280.32
Chemical PropertiesBack Directory
[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 DataBack Directory
[WGK Germany ]

3
Hazard InformationBack Directory
[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.
[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).
[Biological Activity]

A potent inhibitor of phosphatidic acid generation (IC50=0.6 μM). It protects mice from endotoxic shock and attenuates sepsis-induced acute lung injury in the pig. Anti-inflammatory agent. Enhances glucose-stimulated insulin secretion. Inhibits IL-12-mediated STAT4 activation.
[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) Yang?et al. (2005),?Lisofylline: a potential lead for the treatment of diabetes; Biochem. Pharmacol., 69?1 2) Yang?et al. (2002),?The anti-inflammatory compound lisofylline prevents Type I diabetes in non-obese diabetic mice; Diabetologia,?45?1307 3) Wyska?et al. (2010),?Pharmacokinetic-pharmacodynamic modeling of methylxanthine derivatives in mice challenged with high-dose lipopolysaccharide; Pharmacology,?85?264
Spectrum DetailBack Directory
[Spectrum Detail]

HYDROXY PENTOXIFYLLINE(6493-06-7)1HNMR
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