NCX-4016   Click here for help

GtoPdb Ligand ID: 9018

Synonyms: NCX 4016 | NCX4016 | nitric oxide-releasing aspirin | nitroaspirin
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: NCX-4016 is an inhibitor which supports generation of reactive oxygen species (ROS) that modify CCL2 levels, disabling T cell chemotaxis. It is expected that this type of action will have anti-inflammatory, antiproliferative, and cytoprotective activity [1]. NCX-4016 is a NO-NSAID type compound (nitric oxide-donating NSAID), a hybrid nitrate conjugated to an NSAID, in this case aspirin. This type of compound was designed to exploit the gastroprotective properties of NO bioactivity, to combat the gastrotoxicity which compromises NSAID use [2].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 104.97
Molecular weight 331.07
XLogP 3.45
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES [O-][N+](=O)OCc1cccc(c1)OC(=O)c1ccccc1OC(=O)C
Isomeric SMILES [O-][N+](=O)OCc1cccc(c1)OC(=O)c1ccccc1OC(=O)C
InChI InChI=1S/C16H13NO7/c1-11(18)23-15-8-3-2-7-14(15)16(19)24-13-6-4-5-12(9-13)10-22-17(20)21/h2-9H,10H2,1H3
InChI Key IOJUJUOXKXMJNF-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
NCX-4016 reached Phase II clinical trial in patients with type 2 diabetes and early nephropathy (NCT00157508, terminated) and those with peripheral arterial occlusive disease (PAOD; NCT01256775, completed but not progressed). Despite showing positive results in pre-clinical testing [2] , these effects in colorectal cancer were not replicated in a Phase I trial (NCT01256775).