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
1. Gudin J, Rauck R, Argoff C, Agaiby E, Gimbel J, Katz N, Doberstein SK, Tagliaferri M, Tagliaferri M, Potts J et al.. (2020)
Long-term Safety and Tolerability of NKTR-181 in Patients with Moderate to Severe Chronic Low Back Pain or Chronic Noncancer Pain: A Phase 3 Multicenter, Open-Label, 52-Week Study (SUMMIT-08 LTS).
Pain Med, 21 (7): 1347-1356. [PMID:31361019]
2. Lanier RK, Henningfield JE, Gudin J, Rauck R, Elder H, Erpelding N, Treister R, Gimbel J, Tagliaferri M, Doberstein SK et al.. (2019)
Assessment of potentially abuse-related events in two phase 3 studies of NKTR-181, a novel opioid analgesic, using the MADDERS® system (Misuse, Abuse, and Diversion Drug Event Reporting System).
Curr Med Res Opin, 35 (9): 1513-1522. [PMID:30932719]
3. Miyazaki T, Choi IY, Rubas W, Anand NK, Ali C, Evans J, Gursahani H, Hennessy M, Kim G, McWeeney D et al.. (2017)
NKTR-181: A Novel Mu-Opioid Analgesic with Inherently Low Abuse Potential.
J Pharmacol Exp Ther, 363 (1): 104-113. [PMID:28778859]