oxycodegol   Click here for help

GtoPdb Ligand ID: 10652

Synonyms: loxicodegol (deleted INN) | NKTR-181 | NKTR181
Compound class: Synthetic organic
Comment: Oxycodegol (NKTR-181; Nektar Therapeutics) is a μ-opioid receptor agonist analgesic [3]. It was designed to enter the brain slowly, so as to reduce CNS-mediated side effects and abuse potential.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 1
Rotatable bonds 20
Topological polar surface area 106.54
Molecular weight 595.34
XLogP -0.47
No. Lipinski's rules broken 1
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Canonical SMILES COCCOCCOCCOCCOCCOCCO[C@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1OC)O
Isomeric SMILES COCCOCCOCCOCCOCCOCCO[C@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1OC)O
InChI InChI=1S/C31H49NO10/c1-32-9-8-30-27-23-4-5-24(35-3)28(27)42-29(30)25(6-7-31(30,33)26(32)22-23)41-21-20-40-19-18-39-17-16-38-15-14-37-13-12-36-11-10-34-2/h4-5,25-26,29,33H,6-22H2,1-3H3/t25-,26+,29-,30-,31+/m0/s1
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Summary of Clinical Use Click here for help
Development progressed to completion of Phase 3 trials in chronic pain conditions [1-2], and to submission of a New Drug Application (NDA) to the FDA. However, upon unfavourable reviews by the FDA which concluded that the drug was unlikely to be approved, Nektar withdrew the NDA and terminated the development program.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02367820 Long-Term Safety and Tolerability Study of NKTR-181 in Subjects With Chronic Low Back Pain or Chronic Non-Cancer Pain Phase 3 Interventional Nektar Therapeutics