varespladib   Click here for help

GtoPdb Ligand ID: 9657

Synonyms: compound 6m [PMID: 8978844] | LY315920 | S-5920 | varespladib methyl (A-002) | varespladib sodium (A-001)
PDB Ligand Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Varespladib (LY315920) is a secretory phospholipase A2 (sPLA2) inhibitor [1-2] in clinical development. The administered form can be varespladib sodium (A-001, for intravenuous administration) or varespladib methyl (A-002, for oral administration). The history of varespladib's discovery and development is summarized in [3].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 111.62
Molecular weight 380.14
XLogP 2.39
No. Lipinski's rules broken 0
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Canonical SMILES CCc1c(C(=O)C(=O)N)c2c(n1Cc1ccccc1)cccc2OCC(=O)O
Isomeric SMILES CCc1c(C(=O)C(=O)N)c2c(n1Cc1ccccc1)cccc2OCC(=O)O
InChI InChI=1S/C21H20N2O5/c1-2-14-19(20(26)21(22)27)18-15(9-6-10-16(18)28-12-17(24)25)23(14)11-13-7-4-3-5-8-13/h3-10H,2,11-12H2,1H3,(H2,22,27)(H,24,25)
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Summary of Clinical Use Click here for help
Varespladib completed Phase 2 clinical trial for acute coronary syndrome (ACS). A Phase 3 trial in ACS was terminated (NCT01130246), as was a Phase 2 trial for vaso-occlusive crisis in sickle cell disease (NCT01522196). Varespladib sodium's FDA orphan drug designation (ODD) for prevention of acute chest syndrome in at-risk patients with sickle cell disease has been withdrawn (link here to access the FDA's report for this ODD).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Varespladib disrupts the first step of the arachidonic acid pathway of inflammation, and therefore has anti-inflammatory action.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT01130246 VISTA-16 Trial: Evaluation of Safety and Efficacy of Short-term A-002 Treatment in Subjects With Acute Coronary Syndrome Phase 3 Interventional Anthera Pharmaceuticals
NCT01522196 A Study of Varespladib Infusion in Subjects With Sickle Cell Disease. Phase 2 Interventional Anthera Pharmaceuticals