Methylnaltrexone

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

What is the Methylnaltrexone?

The molecule Methylnaltrexone presents a molecular formula of C21H26NO4+ and its IUPAC name is (4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-one.

Methylnaltrexone (INN) is an opioid antagonist used in the treatment of opioid-induced constipation. It is a derivative of naltrexone and is structurally similar to levomethadyl acetate. Methylnaltrexone was approved by the U.S. Food and Drug Administration (FDA) in 2008..

Methylnaltrexone is a quaternary amine and therefore does not cross the blood-brain barrier, which limits its efficacy to peripheral opioid receptors. This makes it useful for treating the constipating effects of opioids without affecting their analgesic properties..

Methylnaltrexone was first synthesized in the early 1980s. It was originally developed as an opioid antagonist for use in the treatment of drug addiction. However, it was found to be ineffective in this role..

In 2004, methylnaltrexone was approved in the United States for the treatment of opioid-induced constipation in patients with advanced illness. It exists as a subcutaneous injection..

The most common side effects of methylnaltrexone are abdominal pain, diarrhea, flatulence, and nausea. These side effects are generally mild and resolve with continued treatment..

Methylnaltrexone is a safe and effective treatment for opioid-induced constipation. It is well tolerated, with the most common side effects being mild and resolve with continued treatment..

3D structure

Cartesian coordinates

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

2D drawing

 

Methylnaltrexone JVLBPIPGETUEET-GAAHOAFPSA-O chemical compound 2D structure molecule svg
Methylnaltrexone

 

Molecule descriptors

 
IUPAC name(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-one
InChI codeInChI=1S/C21H25NO4/c1-22(11-12-2-3-12)9-8-20-17-13-4-5-14(23)18(17)26-19(20)15(24)6-7-21(20,25)16(22)10-13/h4-5,12,16,19,25H,2-3,6-11H2,1H3/p+1/t16-,19+,20+,21-,22?/m1/s1
InChI KeyJVLBPIPGETUEET-GAAHOAFPSA-O
SMILESC[N+]1(CC2CC2)CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)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,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-3-ium-7-one
  • 17-(Cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxymorphinanium-6-one
  • 17-(Cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxy-17-methyl-6-oxomorphinanium
  • 83387-25-1
  • BDBM50278337
  • GTPL7563
  • MNTX
  • MRZ 2663
  • MRZ-2663BR
  • Methylnaltrexone
  • Methylnaltrexonium
  • Morphinanium, 17-(cyclopropylmethyl)-4,5-epoxy-3,14-dihydroxy-17-methyl-6-oxo-, (5alpha)-
  • Mrz-2663
  • N-Methylnaltrexone
  • NCGC00378877-01
  • Naltrexone MB
  • Q411515
  • Quaternary ammonium naltrexone

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC5764759
  • DTXSID20873339
  • CHEMBL470617
  • CHEMBL1186579
  • CHEBI:136007
  • SCHEMBL49356

Physico-Chemical properties

IUPAC name(4R,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a,9-dihydroxy-3-methyl-2,4,5,6,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-3-ium-7-one
Molecular formulaC21H26NO4+
Molecular weight356.435
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity101.15
LogP1.6
Topological polar surface area66.8

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.