Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C13H20N4O3 |
| Molecular Weight | 280.3229 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H](O)CCCCN1C(=O)N(C)C2=C(N(C)C=N2)C1=O
InChI
InChIKey=NSMXQKNUPPXBRG-SECBINFHSA-N
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
| Molecular Formula | C13H20N4O3 |
| Molecular Weight | 280.3229 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Lisofylline [1-(5R-hydroxyhexyl)-3,7-dimethylxanthine] is a unique metabolite of pentoxifylline. Lisofylline inhibited the generation of phosphatidic acid and free fatty acids. Lisofylline blocked the release of pro-inflammatory cytokines in oxidative tissue injury, in response to cancer chemotherapy and in experimental sepsis. Lisofylline regulates immune cell function and autoimmune response by inhibition of IL-12 signalling and cytokine production. Lisofylline may have therapeutic value in the prevention of autoimmune disorders, including Type 1 diabetes, autoimmune recurrence following islet transplantation, and in preservation of beta cell functional mass during islet isolation.
Originator
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5698 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9435196 |
3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
LISOFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
226 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9435196 |
226 mg/kg single, oral dose: 226 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LISOFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
10.88 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10673700 |
3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
LISOFYLLINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2756 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9435196 |
3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
LISOFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
343 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9435196 |
226 mg/kg single, oral dose: 226 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LISOFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.77 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9435196 |
3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
LISOFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
0.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9435196 |
226 mg/kg single, oral dose: 226 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
LISOFYLLINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
3 mg/kg 1 times / 6 hours multiple, intravenous Studied dose Dose: 3 mg/kg, 1 times / 6 hours Route: intravenous Route: multiple Dose: 3 mg/kg, 1 times / 6 hours Sources: Page: p.286 |
unhealthy, ADULT n = 19 Health Status: unhealthy Condition: Hematologic malignancy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 19 Sources: Page: p.286 |
Disc. AE: Feelings of weakness, Vasodilatation... AEs leading to discontinuation/dose reduction: Feelings of weakness (5.3%) Sources: Page: p.286Vasodilatation (5.3%) Seizures (5.3%) Nausea (10.5%) Vomiting (10.5%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Nausea | 10.5% Disc. AE |
3 mg/kg 1 times / 6 hours multiple, intravenous Studied dose Dose: 3 mg/kg, 1 times / 6 hours Route: intravenous Route: multiple Dose: 3 mg/kg, 1 times / 6 hours Sources: Page: p.286 |
unhealthy, ADULT n = 19 Health Status: unhealthy Condition: Hematologic malignancy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 19 Sources: Page: p.286 |
| Vomiting | 10.5% Disc. AE |
3 mg/kg 1 times / 6 hours multiple, intravenous Studied dose Dose: 3 mg/kg, 1 times / 6 hours Route: intravenous Route: multiple Dose: 3 mg/kg, 1 times / 6 hours Sources: Page: p.286 |
unhealthy, ADULT n = 19 Health Status: unhealthy Condition: Hematologic malignancy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 19 Sources: Page: p.286 |
| Feelings of weakness | 5.3% Disc. AE |
3 mg/kg 1 times / 6 hours multiple, intravenous Studied dose Dose: 3 mg/kg, 1 times / 6 hours Route: intravenous Route: multiple Dose: 3 mg/kg, 1 times / 6 hours Sources: Page: p.286 |
unhealthy, ADULT n = 19 Health Status: unhealthy Condition: Hematologic malignancy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 19 Sources: Page: p.286 |
| Seizures | 5.3% Disc. AE |
3 mg/kg 1 times / 6 hours multiple, intravenous Studied dose Dose: 3 mg/kg, 1 times / 6 hours Route: intravenous Route: multiple Dose: 3 mg/kg, 1 times / 6 hours Sources: Page: p.286 |
unhealthy, ADULT n = 19 Health Status: unhealthy Condition: Hematologic malignancy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 19 Sources: Page: p.286 |
| Vasodilatation | 5.3% Disc. AE |
3 mg/kg 1 times / 6 hours multiple, intravenous Studied dose Dose: 3 mg/kg, 1 times / 6 hours Route: intravenous Route: multiple Dose: 3 mg/kg, 1 times / 6 hours Sources: Page: p.286 |
unhealthy, ADULT n = 19 Health Status: unhealthy Condition: Hematologic malignancy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Population Size: 19 Sources: Page: p.286 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Lisofylline: a potential lead for the treatment of diabetes. | 2005 Jan 1 |
|
| Pentoxifylline and its major oxidative metabolites exhibit different pharmacological properties. | 2006 Mar 27 |
|
| Pentoxifylline as an adjunct therapy in children with cerebral malaria. | 2010 Dec 21 |
Patents
Sample Use Guides
A multicenter, randomized placebo-controlled trial was performed in patients with hematologic malignancies receiving bone marrow transplantation from HLA-identical sibling donors. Patients were randomized to receive either placebo, 2 mg/kg lisofylline or 3 mg/kg lisofylline every 6 h, beginning before conditioning and continuing to day 21 or hospital discharge.
Route of Administration:
Intravenous
Human blood was stimulated with various endotoxin preparations, zymosan, or protein A, and the levels of secreted monokines were measured by enzyme-linked immunosorbent assay. CT-1501R (lisofylline) inhibited tumor necrosis factor alpha (TNF-alpha), interleukin 1 beta (IL-1 beta), and IL-6 release in a dose-dependent manner and was active with all stimuli tested including Salmonella and Escherichia coli-derived endotoxin, endotoxin from both rough and smooth E. coli strains, as well as zymosan and protein A. CT-1501R inhibited monokine release by approximately 50% at 200 microM and 30% at 50 microM and was independent of the relative potency of stimulus. CT-1501R also inhibited IL-1 alpha or IL-1 beta induction of either TNF-alpha or IL-1 beta and inhibited the synergistic effects of stimulation with both human IL-1 beta and murine TNF-alpha on release of human TNF-alpha. Inhibition of monokine release following stimulation with monokine(s) was, in general, greater than that achieved with lipopolysaccharide (LPS) stimulation.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:24:20 UTC 2023
by
admin
on
Sat Dec 16 17:24:20 UTC 2023
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| Record UNII |
L1F2Q2X956
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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NCI_THESAURUS |
C744
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m6843
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100324-81-0
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143527
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Lisofylline
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C025189
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100000082544
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FF-20
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C1516
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7322
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L1F2Q2X956
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CHEMBL1411
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METABOLITE ACTIVE -> PARENT |
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