naloxegol   Click here for help

GtoPdb Ligand ID: 7539

Synonyms: AZ-13337019 | AZ13337019 | Movantik® | Moventig® | NKTR-118
Approved drug
naloxegol is an approved drug (EMA & FDA (2014))
Compound class: Synthetic organic
Comment: Naloxegol is a PEGylated version of naloxol (α-naloxol PubChem CID 5492271; β-naloxol PubChem CID 5492293). PEGylation reduces the compound's ability to cross the blood-brain barrier, therefore restricting CNS penetration. Naloxegol is termed a peripherally acting μ-opioid receptor antagonist, or PAMORA. The synonyms suffixed with "oxalate " map to the salt as PubChem CID 56959086
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 10
Hydrogen bond donors 2
Rotatable bonds 24
Topological polar surface area 126.77
Molecular weight 651.36
XLogP -0.36
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES COCCOCCOCCOCCOCCOCCOCCOC1CCC2(C34C1Oc1c4c(CC2N(CC3)CC=C)ccc1O)O
Isomeric SMILES COCCOCCOCCOCCOCCOCCOCCO[C@H]1CC[C@@]2([C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)CC=C)ccc1O)O
InChI InChI=1S/C34H53NO11/c1-3-9-35-10-8-33-30-26-4-5-27(36)31(30)46-32(33)28(6-7-34(33,37)29(35)25-26)45-24-23-44-22-21-43-20-19-42-18-17-41-16-15-40-14-13-39-12-11-38-2/h3-5,28-29,32,36-37H,1,6-25H2,2H3/t28-,29+,32-,33-,34+/m0/s1
InChI Key XNKCCCKFOQNXKV-ZRSCBOBOSA-N
References
1. Holzer P. (2008)
New approaches to the treatment of opioid-induced constipation.
Eur Rev Med Pharmacol Sci, 12 Suppl 1: 119-27. [PMID:18924451]
2. Panchal SJ, Müller-Schwefe P, Wurzelmann JI. (2007)
Opioid-induced bowel dysfunction: prevalence, pathophysiology and burden.
Int J Clin Pract, 61 (7): 1181-7. [PMID:17488292]
3. Pappagallo M. (2001)
Incidence, prevalence, and management of opioid bowel dysfunction.
Am J Surg, 182 (5A Suppl): 11S-18S. [PMID:11755892]
4. Webster L, Dhar S, Eldon M, Masuoka L, Lappalainen J, Sostek M. (2013)
A phase 2, double-blind, randomized, placebo-controlled, dose-escalation study to evaluate the efficacy, safety, and tolerability of naloxegol in patients with opioid-induced constipation.
Pain, 154 (9): 1542-50. [PMID:23726675]