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100324-81-0,MFCD00867573
Catalog No.:AA0001JQ
100324-81-0 | 1H-Purine-2,6-dione, 3,7-dihydro-1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl-
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1mg
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$142.00   $100.00
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5mg
≥97%
1 week  
$460.00   $322.00
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10mg
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Technical Information
Catalog Number:
AA0001JQ
Chemical Name:
1H-Purine-2,6-dione, 3,7-dihydro-1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl-
CAS Number:
100324-81-0
Molecular Formula:
C13H20N4O3
Molecular Weight:
280.3229
MDL Number:
MFCD00867573
IUPAC Name:
1-[(5R)-5-hydroxyhexyl]-3,7-dimethylpurine-2,6-dione
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/t9-/m1/s1
InChI Key:
NSMXQKNUPPXBRG-SECBINFHSA-N
SMILES:
C[C@H](CCCCn1c(=O)c2n(C)cnc2n(c1=O)C)O
UNII:
L1F2Q2X956
Properties
Computed Properties
 
Complexity:
390  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
1  
Defined Bond Stereocenter Count:
0
Exact Mass:
280.154g/mol
Formal Charge:
0
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
280.328g/mol
Monoisotopic Mass:
280.154g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
78.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.7  

Synonyms
 
1-(5'-hydroxyhexyl)-3,7-dimethylxanthine 
1-(5R-hydroxyhexyl)-3,7-dimethylxanthine 
100324-81-0 
Lisophylline 
CT-1501R 
NSMXQKNUPPXBRG-SECBINFHSA-N 
(R)-Lisophylline 
CT 1501R 
3,7-Dihydro-1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl-1H-purine-2,6-dione 
UNII-L1F2Q2X956 
1-[(5R)-5-hydroxyhexyl]-3,7-dimethylpurine-2,6-dione 
lisofilina 
3,7-dimethyl-1-(5-hydroxyhexyl)xanthine 
lisofyllinum 
L1F2Q2X956 
(-)-lisofylline 
ProTec (TN) 
AC1L9UOZ 
Lisofylline (USAN/INN) 
CHEMBL1411 
SCHEMBL39131 
(R)-LSF 
GTPL9225 
A-802710 
DTXSID7058709 
CTK8E6838 
CT1501R 
CHEBI:143527 
LSF 
ZINC1887263 
1836AH 
AKOS025394050 
DB12406 
SB18959 
BL 194 
NCGC00186630-01 
1-(5-R-hydroxyhexyl)-3,7-dimethylxanthine 
FT-0670822 
R-1-(5-Hydroxyhexyl)-3,7-dimethylxanthine 
(r)-1-(5-hydroxyhexyl)-3,7-dimethylxanthine 
D04748 
J-000102 
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 
1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione 
CT-1501R 
Lisofylline [USAN:INN] 
D03WRJ 
1-[(R)-5-hydroxyhexyl]theobromine 
C13H20N4O3 
1-((R)-5-Hydroxyhexyl)theobromine 
CID501254 
C13-H20-N4-O3 
1-(5R-Hydroxyhexyl)-3,7-dimethylxanthine 
1H-Purine-2,6-dione, 3,7-dihydro-1-[(5R)-5-hydroxyhexyl]-3,7-dimethyl- 
lisofylline 
LISOFYLLINE 
(R)-Lisofylline 
ProTec 
Literature

Title: Macrolide antibiotics and survival in patients with acute lung injury.

Journal: Chest 20120501

Title: Macrolides for acute lung injury.

Journal: Chest 20120501

Title: Amelioration of type 1 diabetes following treatment of non-obese diabetic mice with INGAP and lisofylline.

Journal: Journal of diabetes mellitus 20120501

Title: Acute respiratory distress syndrome: pathophysiology and therapeutic options.

Journal: Journal of clinical medicine research 20120201

Title: Catenarin Prevents Type 1 Diabetes in Nonobese Diabetic Mice via Inhibition of Leukocyte Migration Involving the MEK6/p38 and MEK7/JNK Pathways.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: Evidence for activation of inflammatory lipoxygenase pathways in visceral adipose tissue of obese Zucker rats.

Journal: American journal of physiology. Endocrinology and metabolism 20110101

Title: Activation of the GLP-1 receptor signalling pathway: a relevant strategy to repair a deficient beta-cell mass.

Journal: Experimental diabetes research 20110101

Title: Extrinsic factors involved in the differentiation of stem cells into insulin-producing cells: an overview.

Journal: Experimental diabetes research 20110101

Title: Different toll-like receptor stimuli have a profound impact on cytokines required to break tolerance and induce autoimmunity.

Journal: PloS one 20110101

Title: Acute respiratory distress syndrome: A clinical review.

Journal: Pulmonary circulation 20110101

Title: Current status of immunomodulatory and cellular therapies in preclinical and clinical islet transplantation.

Journal: Journal of transplantation 20110101

Title: Targeting ceramide synthesis to reverse insulin resistance.

Journal: Diabetes 20101001

Title: Saturated- and n-6 polyunsaturated-fat diets each induce ceramide accumulation in mouse skeletal muscle: reversal and improvement of glucose tolerance by lipid metabolism inhibitors.

Journal: Endocrinology 20100901

Title: Bioanalysis of pentoxifylline and related metabolites in plasma samples through LC-MS/MS.

Journal: Biomedical chromatography : BMC 20100601

Title: 12-Lipoxygenase Products Reduce Insulin Secretion and {beta}-Cell Viability in Human Islets.

Journal: The Journal of clinical endocrinology and metabolism 20100201

Title: Pharmacokinetic interaction between verapamil and methylxanthine derivatives in mice.

Journal: Drug metabolism letters 20100101

Title: Pharmacokinetic-pharmacodynamic modeling of methylxanthine derivatives in mice challenged with high-dose lipopolysaccharide.

Journal: Pharmacology 20100101

Title: Towards the prevention of acute lung injury: a population based cohort study protocol.

Journal: BMC emergency medicine 20100101

Title: Exenatide: a new promising antidiabetic agent.

Journal: Indian journal of pharmaceutical sciences 20100101

Title: Bedside quantification of dead-space fraction using routine clinical data in patients with acute lung injury: secondary analysis of two prospective trials.

Journal: Critical care (London, England) 20100101

Title: In vivo islet protection by a nuclear import inhibitor in a mouse model of type 1 diabetes.

Journal: PloS one 20100101

Title: Immune depletion with cellular mobilization imparts immunoregulation and reverses autoimmune diabetes in nonobese diabetic mice.

Journal: Diabetes 20091001

Title: The effects of pentoxifylline on skeletal muscle contractility and neuromuscular transmission during hypoxia.

Journal: Indian journal of pharmacology 20091001

Title: Point: steady progress and current challenges in clinical islet transplantation.

Journal: Diabetes care 20090801

Title: Pretreatment with R(+)-verapamil significantly reduces mortality and cytokine expression in murine model of septic shock.

Journal: International immunopharmacology 20090401

Title: Methyltransferase Set7/9 maintains transcription and euchromatin structure at islet-enriched genes.

Journal: Diabetes 20090101

Title: Validation of a high-performance liquid chromatography method for pharmacokinetic evaluation of pentoxifylline and lisofylline in rat serum and tissues.

Journal: Acta poloniae pharmaceutica 20090101

Title: Overexpression of thioredoxin in islets transduced by a lentiviral vector prolongs graft survival in autoimmune diabetic NOD mice.

Journal: Journal of biomedical science 20090101

Title: Effects of pentoxifylline and its metabolites on platelet aggregation in whole blood from healthy humans.

Journal: European journal of pharmacology 20080310

Title: Effects of pentoxifylline on TNF-alpha and lung histopathology in HCL-induced lung injury.

Journal: Clinics (Sao Paulo, Brazil) 20080201

Title: Predictive and pathogenetic value of plasma biomarkers for acute kidney injury in patients with acute lung injury.

Journal: Critical care medicine 20071201

Title: Dilinoleoyl-phosphatidic acid mediates reduced IRS-1 tyrosine phosphorylation in rat skeletal muscle cells and mouse muscle.

Journal: Diabetologia 20070801

Title: Enantioselective reduction of pentoxifylline to lisofylline using whole-cell Lactobacillus kefiri biotransformation.

Journal: Biotechnology journal 20070401

Title: Pharmacokinetic modelling of pentoxifylline and lisofylline after oral and intravenous administration in mice.

Journal: The Journal of pharmacy and pharmacology 20070401

Title: Pharmacokinetics of intranasal and intratracheal pentoxifylline in rabbits.

Journal: Pharmacotherapy 20070201

Title: Prediction of death and prolonged mechanical ventilation in acute lung injury.

Journal: Critical care (London, England) 20070101

Title: Enantioselective biotransformation of pentoxifylline into lisofylline using wine yeast biocatalysis.

Journal: Acta poloniae pharmaceutica 20070101

Title: Intestinal mucosal dysfunction and infection during remission-induction therapy for acute myeloid leukaemia.

Journal: Leukemia 20061201

Title: Interconversion and tissue distribution of pentoxifylline and lisofylline in mice.

Journal: Chirality 20060801

Title: Synthesis and biological evaluation of lisofylline (LSF) analogs as a potential treatment for Type 1 diabetes.

Journal: Bioorganic & medicinal chemistry letters 20060701

Title: Combined treatment with lisofylline and exendin-4 reverses autoimmune diabetes.

Journal: Biochemical and biophysical research communications 20060609

Title: Pharmacological therapy for acute respiratory distress syndrome.

Journal: Mayo Clinic proceedings 20060201

Title: Activation of the 12-lipoxygenase and signal transducer and activator of transcription pathway during neointima formation in a model of the metabolic syndrome.

Journal: American journal of physiology. Endocrinology and metabolism 20060101

Title: Survival methods, including those using competing risk analysis, are not appropriate for intensive care unit outcome studies.

Journal: Critical care (London, England) 20060101

Title: Bench-to-bedside review: the role of glycosaminoglycans in respiratory disease.

Journal: Critical care (London, England) 20060101

Title: Multidose streptozotocin induction of diabetes in BALB/c mice induces a dominant oxidative macrophage and a conversion of TH1 to TH2 phenotypes during disease progression.

Journal: Mediators of inflammation 20050831

Title: Use of liquid chromatography-tandem mass spectrometry for the analysis of pentoxifylline and lisofylline in plasma.

Journal: Biomedical chromatography : BMC 20050401

Title: Inflammatory blockade improves human pancreatic islet function and viability.

Journal: American journal of transplantation : official journal of the American Society of Transplantation and the American Society of Transplant Surgeons 20050301

Title: Lisofylline: a potential lead for the treatment of diabetes.

Journal: Biochemical pharmacology 20050101

Title: Pro/con clinical debate: It is acceptable to stop large multicentre randomized controlled trials at interim analysis for futility. Pro: Futility stopping can speed up the development of effective treatments.

Journal: Critical care (London, England) 20050101

Title: Pentoxifylline inhibits agonist-induced vasoconstriction in vascular smooth muscle and spontaneous peristalsis in isolated ileum.

Journal: Oncology research 20050101

Title: Inflammation blockade improves pancreatic islet function.

Journal: Transplantation proceedings 20041101

Title: Excess body weight is not independently associated with outcome in mechanically ventilated patients with acute lung injury.

Journal: Annals of internal medicine 20040302

Title: Lisofylline, a novel anti-inflammatory agent, enhances glucose-stimulated insulin secretion in vivo and in vitro: studies in prediabetic and normal rats.

Journal: Metabolism: clinical and experimental 20040301

Title: The novel anti-inflammatory agent lisofylline prevents autoimmune diabetic recurrence after islet transplantation.

Journal: Transplantation 20040115

Title: Lisofylline, a novel antiinflammatory compound, protects mesangial cells from hyperglycemia- and angiotensin II-mediated extracellular matrix deposition.

Journal: Endocrinology 20031201

Title: Emerging systemic pharmacologic approaches in acute respiratory distress syndrome.

Journal: Respiratory care clinics of North America 20031201

Title: Inhibition of STAT4 activation by lisofylline is associated with the protection of autoimmune diabetes.

Journal: Annals of the New York Academy of Sciences 20031101

Title: The novel anti-inflammatory compound, lisofylline, prevents diabetes in multiple low-dose streptozotocin-treated mice.

Journal: Pancreas 20030501

Title: The anti-inflammatory compound lisofylline prevents Type I diabetes in non-obese diabetic mice.

Journal: Diabetologia 20020901

Title: Developmental differences in the role of interleukins in hyperoxic lung injury in animal models.

Journal: Frontiers in bioscience : a journal and virtual library 20020701

Title: Lisofylline, a novel antiinflammatory agent, protects pancreatic beta-cells from proinflammatory cytokine damage by promoting mitochondrial metabolism.

Journal: Endocrinology 20020601

Title: Modulation of gastrointestinal wound repair and inflammation by phospholipids.

Journal: Biochimica et biophysica acta 20020523

Title: Specific therapies for inhalation injury.

Journal: Critical care medicine 20020301

Title: Effects of heparin and lisofylline on pulmonary function after smoke inhalation injury in an ovine model.

Journal: Critical care medicine 20020301

Title: Randomized, placebo-controlled trial of lisofylline for early treatment of acute lung injury and acute respiratory distress syndrome.

Journal: Critical care medicine 20020101

Title: Lisofylline: anti-acute respiratory distress syndrome or just anti-inflammatory?

Journal: Critical care medicine 20020101

Title: Lisofylline and lysophospholipids ameliorate experimental colitis in rats.

Journal: Digestion 20020101

Title: Understanding the roles of the transcription factors nuclear factor-kappaB and hypoxia-inducible factor-1alpha in lung injury.

Journal: Critical care (London, England) 20020101

Title: Science review: Redox and oxygen-sensitive transcription factors in the regulation of oxidant-mediated lung injury: role for nuclear factor-kappaB.

Journal: Critical care (London, England) 20020101

Title: Antioxidant and radical scavenging properties of 8-oxo derivatives of xanthine drugs pentoxifylline and lisofylline.

Journal: Biochemical and biophysical research communications 20011116

Title: Immunotherapy of inflammatory demyelinating diseases of the central nervous system.

Journal: Immunologic research 20010101

Title: CT-1501R selectively inhibits induced inflammatory monokines in human whole blood ex vivo.

Journal: Shock (Augusta, Ga.) 19940401

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