navarixin   Click here for help

GtoPdb Ligand ID: 8497

Synonyms: MK-7123 | MK7123 | SCH-527123 | SCH527123
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Navarixin (SCH-527123, MK-7123) is a potent and orally bioavailable CXCR2/CXCR1 receptor antagonist [2].
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 6
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 111.88
Molecular weight 397.16
XLogP 3.39
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CCC(c1ccc(o1)C)NC1=C(C(=O)C1=O)Nc1cccc(c1O)C(=O)N(C)C
Isomeric SMILES CC[C@H](c1ccc(o1)C)NC1=C(C(=O)C1=O)Nc1cccc(c1O)C(=O)N(C)C
InChI InChI=1S/C21H23N3O5/c1-5-13(15-10-9-11(2)29-15)22-16-17(20(27)19(16)26)23-14-8-6-7-12(18(14)25)21(28)24(3)4/h6-10,13,22-23,25H,5H2,1-4H3/t13-/m1/s1
Immunopharmacology Comments
Navarixin failed to show efficacy in inflammatory diseases, but is being evaluated as an adjunct to immune checkpoint inhibition (by pembrolizumab) in advanced solid tumours.
Immunopharmacology Disease
Disease X-Refs Comment References
Psoriasis Disease Ontology: DOID:8893
Completed Phase 2 clinical trial NCT00684593 for psoriasis.
Asthma Disease Ontology: DOID:2841
OMIM: 600807
Completed Phase 2 clinical trial NCT00632502 for asthma.
Chronic obstructive pulmonary disease Disease Ontology: DOID:3083
Clinical trials in COPD were terminated.