6493-06-7

Basic information

• Product Name: HYDROXY PENTOXIFYLLINE
• Synonyms: (+/-)-LISOFYLLINE;LISOFYLLINE;HYDROXY PENTOXIFYLLINE;(+/-)-1-(5-HYDROXYHEXYL)-3,7-DIMETHYLXANTHINE;1-(5-Hydroxyhexyl)-3,7-dimethyl-1,2,3,6-tetrahydro-7H-purine-2,6-dione;Penthydroxifillyne;3,7-Dihydro-1-(5-hydroxyhexyl)-3,7-diMethyl-;5-Hydroxy pentoxifylline
• CAS NO: 6493-06-7
• Molecular Formula: C₁₃H₂₀N₄O₃
• Molecular Weight: 280.32
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 6493-06-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 123-125°C
• Boiling Point: 511.2°Cat760mmHg
• Flash Point: 263°C
• Appearance: white/solid
• Density: 1.32g/cm³
• Storage Temp.: Refrigerator
• Solubility: DMSO: soluble
• PKA: 15.22±0.20(Predicted)
• 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.
• CAS DataBase Reference: HYDROXY PENTOXIFYLLINE(CAS DataBase Reference)
• NIST Chemistry Reference: HYDROXY PENTOXIFYLLINE(6493-06-7)
• EPA Substance Registry System: HYDROXY PENTOXIFYLLINE(6493-06-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6493-06-7(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 6493-06-7 differently. You can refer to the following data:
1. A major oxidative metabolite of Pentoxifylline.
2. 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.

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

Upstream product

• 154719-57-0 1-(5,6-oxidohexyl)-3,7-dimethylxanthine 
• 83-67-0 theobromine / 
• 10226-30-9 6-chloro-2-hexanone 
• 6493-05-6 pentoxyphylline 
• 67-63-0 isopropyl alcohol 
• 67-56-1 methanol 

Downstream Products

• 100324-81-0 lisofylline 
• 100324-80-9 (+)-(S)-3,7-dimethyl-1-(5-hydroxyhexyl)-3,7-dihydropurine-2,6-dione 
• 174455-55-1 6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate 
• 174455-55-1 6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate 
• 174455-55-1 6-(3,7-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-1-yl)hexan-2-yl acetate 
• 117835-33-3 3-Methyl-5-methylamino-3H-imidazole-4-carboxylic acid (5-methoxy-hexyl)-amide; compound with picric acid 

Relevant articles and documents

Two-Step Protocol for Iodotrimethylsilane-Mediated Deoxy-Functionalization of Alcohols

We have developed a two-step protocol for iodotrimethylsilane-mediated deoxy-functionalization of primary and secondary alcohols to afford products containing a C?N, C?S, or C?O bond. In the first step the alcohol undergoes iodination with iodotrimethylsilane, and in the second, the iodine atom is replaced by a N, S, or O nucleophile. Compared with traditional Mitsunobu reaction, non-acidic pre-nucleophiles can be used, and the reaction proceeds with retention of configuration. This operationally simple, highly efficient protocol can be used for some natural products and small-molecule drugs containing hydroxy-group.

Role of Chain Length and Degree of Unsaturation of Fatty Acids in the Physicochemical and Pharmacological Behavior of Drug-Fatty Acid Conjugates in Diabetes

Several drug-fatty acid (FA) prodrugs have been reported to exhibit desirable physicochemical and pharmacological profile; however, comparative beneficial effects rendered by different FAs have not been explored. In the present study, four different FAs (linoleic acid, oleic acid, palmitic acid, and α-lipoic acid) were selected based on their chain length and degree of unsaturation and conjugated to Lisofylline (LSF), an antidiabetic molecule to obtain different drug-FA prodrugs and characterized for molecular weight, hydrophobicity, purity, self-assembly, and efficacy in vitro and in vivo in type 1 diabetes model. Prodrugs demonstrated a 2- to 6-fold increase in the plasma half-life of LSF. Diabetic animals treated with prodrugs, once daily for 5 weeks, maintained a steady fasting blood glucose level with a significant increase in insulin level, considerable restoration of biochemical parameters, and preserved β-cells integrity. Among the different LSF-FA prodrugs, LSF-OA and LSF-PA demonstrated the most favorable physicochemical, systemic pharmacokinetic, and pharmacodynamic profiles.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF CHRONIC DISEASES AND INFLAMMATORY DISORDERS

The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for the treatment of chronic diseases and inflammatory disorders may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of intermittent claudication, obstructed arteries in the limbs, vascular dementia, Peyronie's disease, neuropathic injuries, sickle cell disease, nausea and headaches in the mountains (altitude sickness), acute alcoholic and non-alcoholic steatohepatitis, alcoholic liver disease, fibrotic lesions induced by radiation therapy for cancer, cytokine release syndrome, endometriosis, venous disease, inflammation, cancer, stroke, thrombosis, sepsis, gangrene, infection, type 1 diabetes, type 2 diabetes, pancreatic beta cell degeneration, beta cell dysfunction, respiratory diseases, rheumatoid arthritis, arthritis, osteoarthritis and vascular disease.