(R)-Lisofylline

Modify Date: 2024-01-29 21:05:52

(R)-Lisofylline Structure
(R)-Lisofylline structure
Common Name (R)-Lisofylline
CAS Number 100324-81-0 Molecular Weight 280.323
Density 1.3±0.1 g/cm3 Boiling Point 511.2±56.0 °C at 760 mmHg
Molecular Formula C13H20N4O3 Melting Point N/A
MSDS N/A Flash Point 263.0±31.8 °C

 Use of (R)-Lisofylline


(R)-Lisofylline ((R)-Lisophylline) is a (R)-enantiomer of the metabolite of Pentoxifylline with anti-inflammatory properties. (R)-Lisofylline is a lysophosphatidic acid acyltransferase inhibitor with an IC50 of 0.6 µM and interrupts IL-12 signaling-mediated STAT4 activation. (R)-Lisofylline has the potential for type 1 diabetes, autoimmune disorders research[1][2].

 Names

Name 1-[(5R)-5-hydroxyhexyl]-3,7-dimethylpurine-2,6-dione
Synonym More Synonyms

 (R)-Lisofylline Biological Activity

Description (R)-Lisofylline ((R)-Lisophylline) is a (R)-enantiomer of the metabolite of Pentoxifylline with anti-inflammatory properties. (R)-Lisofylline is a lysophosphatidic acid acyltransferase inhibitor with an IC50 of 0.6 µM and interrupts IL-12 signaling-mediated STAT4 activation. (R)-Lisofylline has the potential for type 1 diabetes, autoimmune disorders research[1][2].
Related Catalog
Target

IC50: 0.6 µM (Lysophosphatidic acid acyltransferase)[1] STAT4[1]

In Vitro (R)-Lisofylline blocks IL-12-driven Th1 differentiation and T cell proliferation in vitro, yet has no effect on IL-12 secretion from APCs ex vivo or in vitro[3].
In Vivo (R)-Lisofylline reduces the impairment of insulin secretion induced by IL-1β in cultured rat islet cells, suppresses IFN-γ production, the onset of diabetes, and macrophage infiltration into islets from NOD mice, as well as Lisofylline improves insulin response and lowers glucose levels in Streptozotocin-treated rats after the oral glucose tolerance test[1]. (R)-Lisofylline prevents β cell dysfunction in NOD mice by inhibition of STAT4 phosphorylation which interrupts IL-12 signaling. (R)-Lisofylline ameliorates experimental allergic encephalomyelitis in mice[1]. (R)-Lisofylline also improves survival in mice injected with a lethal dose of LPS and ameliorates sepsis-induced lung injury in minipigs. In rats given IL-1 intratracheally (R)-Lisofylline pretreatment reduces lung leak but does not decrease neutrophil accumulation in lungs[1]. (R)-Lisofylline also suppresses release of TNF-α in vivo in mice and ex vivo in human blood stimulated with endotoxin derived from Salmonella or Escherichia coli[1].
References

[1]. Elżbieta Wyska, et al. Physiologically Based Modeling of Lisofylline Pharmacokinetics Following Intravenous Administration in Mice. Eur J Drug Metab Pharmacokinet. 2016 Aug;41(4):403-12.

[2]. B M Hybertson, et al. Lisofylline Prevents Leak, but Not Neutrophil Accumulation, in Lungs of Rats Given IL-1 Intratracheally. J Appl Physiol (1985). 1997 Jan;82(1):226-32.

[3]. J J Bright, et al. Prevention of Experimental Allergic Encephalomyelitis via Inhibition of IL-12 Signaling and IL-12-mediated Th1 Differentiation: An Effect of the Novel Anti-Inflammatory Drug Lisofylline. J Immunol. 1998 Dec 15;161(12):7015-22.

 Chemical & Physical Properties

Density 1.3±0.1 g/cm3
Boiling Point 511.2±56.0 °C at 760 mmHg
Molecular Formula C13H20N4O3
Molecular Weight 280.323
Flash Point 263.0±31.8 °C
Exact Mass 280.153534
PSA 82.05000
LogP 0.34
Vapour Pressure 0.0±1.4 mmHg at 25°C
Index of Refraction 1.621

 Synonyms

R-1-(5-Hydroxyhexyl)-3,7-dimethylxanthine
(R)-3,7-Dihydro-1-(5-hydroxyhexyl)-3,7-dimethyl-1H-purine-2,6-dione
Lisophylline
ProTec
1-[(5R)-5-Hydroxyhexyl]-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione
Lisofylline
1H-Purine-2,6-dione, 3,7-dihydro-1-(5-hydroxyhexyl)-3,7-dimethyl-, (R)-
1-[(R)-5-Hydroxyhexyl]theobromine
CT 1501R
CT-1501R
1H-Purine-2,6-dione, 3,7-dihydro-1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl-
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