lisofylline   Click here for help

GtoPdb Ligand ID: 9225

Synonyms: (R)-lisophylline | CT-1501R
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Lisophylline is an active metabolite of pentoxifylline. The compound has novel anti-inflammatory properties, likely through inhibition of IL-12 signalling and STAT-4 activation [2]. It is reported to prevent type 1 diabetes in preclinical models [3] and improve the function and viability of isolated or transplanted pancreatic islets [1]. Evidence suggests that combined treatment with lisofylline (for its anti-inflammatory action) and exendin-4 (to enhance beta-cell proliferation) can reverse autoimmune diabetes in the non-obese diabetic (NOD) mouse model [4].

lisofylline is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 82.05
Molecular weight 280.15
XLogP 2.31
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(CCCCn1c(=O)c2n(C)cnc2n(c1=O)C)O
Isomeric SMILES C[C@H](CCCCn1c(=O)c2n(C)cnc2n(c1=O)C)O
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
A Phase 1/2 clinical trial in patients with type I diabetes mellitus (NCT01603121) was terminated as it was unable to enroll sufficient numbers of subjects.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01603121 Lisofylline as Continuous Subcutaneous and Intravenous Administration in Subjects With Type 1 Diabetes Mellitus Phase 1/Phase 2 Interventional Eastern Virginia Medical School