| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg | |||
| Other Sizes |
| Targets |
(S)-Lisofylline itself does not have a specific molecular target. It is the inactive enantiomer and is used as a negative control. Its major pharmacological feature is its interconversion with the active drug pentoxifylline. It is the exclusive product of pentoxifylline reduction in human liver cytosol. It serves as a metabolic intermediate between (R)-lisofylline and pentoxifylline.
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| ln Vitro |
In human hemolytic red blood cells, (S)-Lisofylline and pentoxifylline can interconvert [2].
No specific in vitro activity data has been reported for (S)-Lisofylline, as it is the inactive enantiomer. Its racemate, Lisofylline, has been shown to preserve beta-cell insulin secretion and inhibit DNA damage of islets in the presence of IL-1beta. It can interconvert with pentoxifylline in human hemolytic erythrocytes. |
| ln Vivo |
(S)-Lisofylline (50 mg/kg; intravenous injection; single dosage) exhibits reduced levels in serum but increased levels in the liver, kidneys, and lungs of mice [2].
No specific in vivo activity data has been reported for (S)-Lisofylline. In a hemorrhagic shock and resuscitation rat model, the racemate Lisofylline (15 mg/kg) increased intestinal and hepatic blood flow and ameliorated mucosal damage and hyperpermeability. It has also been studied in a sheep model of smoke inhalation injury. |
| Enzyme Assay |
(S)-Lisofylline can be used in assays to quantify its conversion to pentoxifylline. For example, the compound is incubated with human liver microsomes (0.5 mg protein/mL) in a buffer containing an NADPH-regenerating system at 37degC. Samples are taken at various time points, and the formation of pentoxifylline is measured by chiral LC-MS/MS. Such assays help determine kinetic parameters for the interconversion.
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| Cell Assay |
(S)-Lisofylline can be used in cell-based assays as a control. For screening, cells (e.g., INS-1 pancreatic cells) are treated with the racemic mixture of Lisofylline (1-100 uM) to study its effects on insulin secretion and cellular metabolism. The (S)-enantiomer can be used as a negative control to establish the stereospecificity of any observed biological effects.
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| Animal Protocol |
No dedicated in vivo animal protocols exist specifically for the (S)-enantiomer. In a study for the racemate, Sprague-Dawley rats (200-250 g) were subjected to hemorrhagic shock, and then (S)-Lisofylline (15 mg/kg, i.v.) was administered. Blood samples were collected for biochemical analysis, and tissues were harvested for histological examination. The compound can also be administered to mice (50 mg/kg, i.v.) to study its tissue distribution.
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| ADME/Pharmacokinetics |
A PBPK model of Lisofylline (the R-enantiomer) in mice estimated an intrinsic hepatic clearance of 5.427 ml/min and a renal clearance of zero. Lisofylline is characterized by a high clearance, short half-life, and reversible metabolism with pentoxifylline, contributing to its poor oral bioavailability. Encapsulation of lisofylline prodrug in micelles significantly improved its oral bioavailability to ~74.86%.
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| Toxicity/Toxicokinetics |
Safety data for lisofylline in humans up to doses of 5.0 mg/kg i.v. show it is generally well tolerated. Side effects at higher doses include light-headedness, dizziness, nausea, and vomiting. Hypotension was also reported in some patients. These side effects are transient and generally resolve within 60 minutes. The compound is not recommended for human or veterinary use outside of clinical trials.
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| References |
[1]. Borowiecki P, et al. Chemoenzymatic deracemization of lisofylline catalyzed by a (laccase/TEMPO)-alcohol dehydrogenase system[J]. Catalysis Science & Technology, 2022, 12(13): 4312-4324.
[2]. Wyska E, et al. Interconversion and tissue distribution of pentoxifylline and lisofylline in mice. Chirality. 2006 Aug;18(8):644-51. |
| Additional Infomation |
(S)-Lisoferine is a 1-(5-hydroxyhexyl)-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione with the (S)-configuration. It is the inactive optical enantiomer of the anti-inflammatory drug (R)-Lisoferine. It is the enantiomer of (R)-Lisoferine.
(S)-Lisofylline is the inactive enantiomer of the anti-inflammatory agent (R)-lisofylline. It serves as a key intermediate in understanding the stereospecific metabolism of pentoxifylline. While pentoxifylline is exclusively reduced to the (S)-enantiomer in human cytosol, (R)-lisofylline is considered the biologically active form. Its 3.3 mg/kg i.v. dose every six hours has been studied in clinical trials for bone marrow transplantation and AML, but the (S)-enantiomer itself has no therapeutic use. |
| Molecular Formula |
C13H20N4O3
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|---|---|
| Molecular Weight |
280.32
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| Exact Mass |
280.153
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| CAS # |
100324-80-9
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| Related CAS # |
(R)-Lisofylline;100324-81-0;(±)-Lisofylline;6493-06-7
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| PubChem CID |
23519621
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
511.2±56.0 °C at 760 mmHg
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| Flash Point |
263.0±31.8 °C
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| Vapour Pressure |
0.0±1.4 mmHg at 25°C
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| Index of Refraction |
1.621
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| LogP |
0.34
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
20
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| Complexity |
390
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C[C@@H](CCCCN1C(=O)C2=C(N=CN2C)N(C)C1=O)O
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| InChi Key |
NSMXQKNUPPXBRG-VIFPVBQESA-N
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| InChi Code |
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-/m0/s1
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| Chemical Name |
1-[(5S)-5-hydroxyhexyl]-3,7-dimethylpurine-2,6-dione
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO: 50 mg/mL (178.37 mM)
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5674 mL | 17.8368 mL | 35.6735 mL | |
| 5 mM | 0.7135 mL | 3.5674 mL | 7.1347 mL | |
| 10 mM | 0.3567 mL | 1.7837 mL | 3.5674 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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