Compound: Naloxegol
SMILES: O1c2c(O)ccc3c2[C@@]45[C@@H]1[C@@H](OCCOCCOCCOCCOCCOCCOCCOC)CC[C@@]4(O)[C@H](N(CC=C)CC5)C3
InChIKey: XNKCCCKFOQNXKV-ZRSCBOBOSA-N
Synonyms: Naloxegol, 854601-70-0, NKTR-118, moventig, NKTR118, NKTR 118, 44T7335BKE, AZ13337019, AZ-13337019, (4R,4aS,7S,7aR,12bS)-7-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]-3-prop-2-enyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol, CHEBI:82975, DTXSID80234684, naloxegolum, (4R,4aS,7S,7aR,12bS)-7-(2-(2-(2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)-3-prop-2-enyl-1,2,4,5,6,7,7a,13-octahydro-4,12-methanobenzofuro(3,2-e)isoquinoline-4a,9-diol, RefChem:57232, A06AH03, DTXCID10157175, (1S,5R,13R,14S,17S)-14-(2,5,8,11,14,17,20-heptaoxadocosan-22-yloxy)-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo(9.6.1.01,13.0?,1?.0?,1?)octadeca-7,9,11(18)-triene-10,17-diol, (5alpha,6alpha)-4,5-Epoxy-6-(3,6,9,12,15,18,21-heptaoxadocos-1-yloxy)-17-(2-propen-1-yl)morphinan-3,14-diol, Morphinan-3,14-diol, 4,5-Epoxy-6-(3,6,9,12,15,18,21-heptaoxadocos-1-yloxy)-17-(2-propenyl)-, (5alpha,6alpha)-, Movantik, Naloxegol [INN], Naloxegol [USAN:INN], UNII-44T7335BKE, Morphinan-3,14-diol, 4,5-epoxy-6-(3,6,9,12,15,18,21-heptaoxadocos-1-yloxy)-17-(2-propen-1-yl)-, (5a,6a)-; Morphinan-3,14-diol, 4,5-epoxy-6-(3,6,9,12,15,18,21-heptaoxadocos-1-yloxy)-17-(2-propenyl)-, (5a,6a)- (9CI); (5a,6a)-4,5-Epoxy-6-(3,6,9,12,15,18,21-h, Naloxone Impurity 20, NALOXEGOL [MI], Naloxegol (USAN/INN), NALOXEGOL [USAN], Naloxegol (NKTR-118), NALOXEGOL [WHO-DD], NALOXEGOL [NFLIS-DRUG], GTPL7539, orb1693794, CHEMBL2219418, SCHEMBL19433066, HSDB 8338, XNKCCCKFOQNXKV-ZRSCBOBOSA-N, GLXC-23930, HY-A0118, ARD193816, EBC-27414, NSC787509, AKOS030526932, CS-4987, DB09049, NSC-787509, NCGC00509863-01, DA-65916, D10479, EN300-22211334, BRD-K41458421-034-01-6, Q15708351, (1S,5R,13R,14S,17S)-14-(2,5,8,11,14,17,20-heptaoxadocosan-22-yloxy)-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-triene-10,17-diol, (4R,4aS,7S,7aR,12bS)-7-((2,5,8,11,14,17,20-heptaoxadocosan-22-yl)oxy)-3-allyl-1,2,3,4,5,6,7,7a-octahydro-4aH-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,9-diol, (5alpha,6alpha)-17-Allyl-6-[(20-hydroxy-3,6,9,12,15,18-hexaoxaicos-1-yl)oxy]-4,5-epoxymorphinan-3,14-diol, 4,5.ALPHA.-EPOXY-6.ALPHA.-((3,6,7,12,15,18,21-HEPTAOXADOCOSYL)OXY)-17-(PROP-2-ENYL)MORPHINAN-3,14-DIOL, 6alpha-[(2,5,8,11,14,17,20-Heptaoxadocosan-22-yl)oxy]-17-(prop-2-en-1-yl)-5alpha-4,5-epoxymorphinan-3,14-diol, Morphinan-3,14-diol, 4,5-epoxy-6-(3,6,9,12,15,18,21-heptaoxadocos-1-yloxy)-     17-(2-propenyl)-, (5alpha,6alpha)-, MORPHINAN-3,14-DIOL, 4,5-EPOXY-6-(3,6,9,12,15,18,21-HEPTAOXADOCOS-1-YLOXY)-17-(2-PROPEN-1-YL)-, (5.ALPHA.,6.ALPHA.)-
Theoretical properties:
molecular_formula: C34H53NO11
molecular_weight: 651.8 g/mol
exact_mass: 651.36186151 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 12
rotatable_bond_count: 24
heavy_atom_count: 46
topological_polar_surface_area: 127 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Naloxegol is an organic heteropentacyclic compound that is naloxone in which the keto group is replaced by a PEG moiety. Used for treatment of opioid-induced constipation. It has a role as a mu-opioid receptor antagonist and a cathartic. It is a tertiary alcohol, a member of phenols, an aromatic ether, an organic heteropentacyclic compound and a polyether. It is functionally related to a naloxone. It derives from a hydride of a morphinan.
chebi: An organic heteropentacyclic compound that is naloxone in which the keto group is replaced by a PEG moiety. Used for treatment of opioid-induced constipation.
chembl: NALOXEGOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Naloxegol (INN; PEGylated naloxol; trade names Movantik and Moventig) is a peripherally acting μ-opioid receptor antagonist developed by AstraZeneca, licensed from Nektar Therapeutics, for the treatment of opioid-induced constipation. It was approved in 2014 in adult patients with chronic, non-cancer pain. Doses of 25 mg were found safe and well tolerated for 52 weeks. When given concomitantly with opioid analgesics, naloxegol reduced constipation-related side effects, while maintaining comparable levels of analgesia.
The most common side effects are abdominal pain, diarrhea, nausea, flatulence, vomiting, and headache.
Naloxegol was previously a Schedule II drug in the United States because of its chemical similarity to noroxymorphone. It was officially decontrolled in January 2015. It was reclassified as a prescription drug after the FDA and DEA concluded that the impermeability of the blood–brain barrier to this compound made it non-habit-forming, and so without the potential for abuse.