Naloxegol

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Naloxegol are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Naloxegol?

The molecule Naloxegol presents a molecular formula of C34H53NO11 and its IUPAC name is (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.

Naloxegol is a peripherally-acting mu-opioid receptor antagonist used in the treatment of opioid-induced constipation. It was discovered by researchers at AstraZeneca. Naloxegol was approved by the U.S. Food and Drug Administration (FDA) in 2012..

Naloxegol is structurally similar to the opioid antagonist naloxone. However, naloxone is a short-acting drug that is rapidly metabolized and has poor oral bioavailability, whereas naloxegol is a long-acting drug with good oral bioavailability..

Naloxegol is metabolized by CYP3A4 and P-glycoprotein. The major metabolite of naloxegol is M3, which is pharmacologically active..

The half-life of naloxegol is 12 hours. Naloxegol is eliminated primarily by fecal excretion..

Naloxegol is indicated for the treatment of opioid-induced constipation in adults with non-cancer pain. The recommended dose of naloxegol is 25 mg once daily with or without food..

Naloxegol is generally well-tolerated. The most common adverse reactions (>2% and greater than placebo) are abdominal pain, diarrhea, flatulence, and nausea..

Naloxegol has a boxed warning for the potential risk of serious or life-threatening allergic reactions. Patients should be instructed to discontinue naloxegol and seek immediate medical attention if they experience signs or symptoms of an allergic reaction..

3D structure

Cartesian coordinates

Geometry of Naloxegol in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Naloxegol XNKCCCKFOQNXKV-ZRSCBOBOSA-N chemical compound 2D structure molecule svg
Naloxegol

 

Molecule descriptors

 
IUPAC name(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
InChI codeInChI=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 KeyXNKCCCKFOQNXKV-ZRSCBOBOSA-N
SMILESC=CCN1CC[C@]23c4c5ccc(O)c4O[C@H]2[C@@H](OCCOCCOCCOCCOCCOCCOCCOC)CC[C@@]3(O)[C@H]1C5

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (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
  • (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
  • 44T7335BKE
  • 854601-70-0
  • AZ-13337019
  • AZ13337019
  • CS-4987
  • D10479
  • DB09049
  • GTPL7539
  • HSDB 8338
  • HY-A0118
  • 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.)-
  • Morphinan-3,14-diol, 4,5-epoxy-6-(3,6,9,12,15,18,21-heptaoxadocos-1-yloxy)- 17-(2-propenyl)-, (5alpha,6alpha)-
  • Movantik
  • NCGC00509863-01
  • NKTR 118
  • NKTR-118
  • NKTR118
  • NSC-787509
  • NSC787509
  • Naloxegol
  • Naloxegol (USAN/INN)
  • Q15708351
  • moventig

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC95564694
  • UNII-44T7335BKE
  • DTXSID80234684
  • CHEMBL2219418
  • CHEBI:82975
  • SCHEMBL19433066

Physico-Chemical properties

IUPAC name(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
Molecular formulaC34H53NO11
Molecular weight651.785
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity172.71
LogP1.8
Topological polar surface area126.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.