Alvimopan

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

What is the Alvimopan?

The molecule Alvimopan presents a molecular formula of C25H32N2O4 and its IUPAC name is 2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanoyl]amino]acetic acid.

Alvimopan (Entereg) is a peripherally-acting mu-opioid receptor antagonist indicated for short-term (generally <15 days) use in conjunction with opioid analgesics to mitigate postoperative ileus following bowel resection surgery. Alvimopan is structurally similar to other peripherally-acting mu-opioid receptor antagonists such as methylnaltrexone and naloxone. However, alvimopan is a synthetic derivative of the plant alkaloid epibatidine and is approximately 1,000 times more selective for the mu-opioid receptor than naloxone. This high degree of selectivity allows alvimopan to block the constipating effects of opioids without affecting their analgesic effects..

Alvimopan is rapidly absorbed following oral administration and has an elimination half-life of approximately 12 hours. Peak plasma concentrations are achieved within 2-3 hours of administration. The bioavailability of alvimopan is approximately 60%. Food does not appear to affect the absorption of alvimopan..

The primary mechanism of action of alvimopan is thought to be the inhibition of gastrointestinal transit by blocking mu-opioid receptors located on enteric neurons. This action slows gastrointestinal motility and transit time, which may help to reduce the severity and duration of postoperative ileus. In addition, alvimopan has been shown to increase colonic blood flow and reduce inflammation..

The most common side effects associated with alvimopan include constipation, nausea, and vomiting. Alvimopan should be used with caution in patients with renal impairment as it is eliminated primarily by the kidney..

Alvimopan is a novel peripherally-acting mu-opioid receptor antagonist that is indicated for short-term use in conjunction with opioid analgesics to mitigate postoperative ileus following bowel resection surgery. Alvimopan has a rapid onset of action and a short elimination half-life, making it an ideal agent for the management of postoperative ileus. The most common side effects associated with alvimopan are constipation, nausea, and vomiting. Alvimopan should be used with caution in patients with renal impairment..

3D structure

Cartesian coordinates

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

2D drawing

 

Alvimopan UPNUIXSCZBYVBB-JVFUWBCBSA-N chemical compound 2D structure molecule svg
Alvimopan

 

Molecule descriptors

 
IUPAC name2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanoyl]amino]acetic acid
InChI codeInChI=1S/C25H32N2O4/c1-18-16-27(12-11-25(18,2)21-9-6-10-22(28)14-21)17-20(24(31)26-15-23(29)30)13-19-7-4-3-5-8-19/h3-10,14,18,20,28H,11-13,15-17H2,1-2H3,(H,26,31)(H,29,30)/t18-,20-,25+/m0/s1
InChI KeyUPNUIXSCZBYVBB-JVFUWBCBSA-N
SMILESC[C@H]1CN(C[C@H](Cc2ccccc2)C(=O)NCC(=O)O)CC[C@@]1(C)c1cccc(O)c1

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.

  • (((2S)-2-(((3R,4R)-4-(3-HYDROXYPHENYL)-3,4-DIMETHYLPIPERIDIN-1-YL)METHYL)-3-PHENYLPROPANOYL)AMINO)ACETIC ACID
  • ((2(S)-((4(R)-(3-HYDROXYPHENYL)-3(R),4-DIMETHYL-1-PIPERIDINYL)METHYL)-1-OXO-3-PHENYLPROPYL)AMINO)ACETIC ACID
  • ((S)-2-benzyl-3-((3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)propanoyl)glycine
  • 053A893
  • 145590-44-9
  • 156053-89-3
  • 2-((S)-2-benzyl-3-((3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)propanamido)acetic acid
  • 2-((S)-2-benzyl-3-((3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)propanamido)aceticacid
  • 2-[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanamido]acetic acid
  • 2-[[(2S)-2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]methyl]-3-phenylpropanoyl]amino]acetic acid
  • 2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanoyl]amino]acetic acid
  • AS-35088
  • Adl 8-2698
  • Alvimopan
  • Alvimopan anhydrous
  • BDBM50088381
  • CS-0536
  • DB06274
  • GLYCINE, N-(2-((4-(3-HYDROXYPHENYL)-3,4-DIMETHYL-1-PIPERIDINYL)METHYL)-1-OXO-3-PHENYLPROPYL)-, (3R-((S*),3.ALPHA.,4.ALPHA.))-
  • GTPL7471
  • Glycine, N-((2S)-2-(((3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl)methyl)-1-oxo-3-phenylpropyl)-
  • Glycine, N-[(2S)-2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]-
  • HMS3886B09
  • HSDB 7704
  • HY-13243
  • LY 246736
  • LY-246736
  • LY246736
  • MFCD09838268
  • N-((2S)-2-(((3R,4R)-4-(3-HYDROXYPHENYL)-3,4-DIMETHYL-1-PIPERIDINYL)METHYL)-1-OXO-3-PHENYLPROPYL)GLYCINE
  • N-[(2S)-2-{[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]methyl}-3-phenylpropanoyl]glycine
  • NCGC00378640-01
  • NCGC00378640-02
  • NCGC00378640-03
  • NG0
  • Q153V49P3Z
  • Q4738021
  • SR-01000945029
  • SR-01000945029-1
  • [[(S)-2-Benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propionyl]amino]acetic acid
  • anhydrous alvimopan
  • s5935
  • trans-3,4-dimethyl-4-(3-hydroxyphenyl) piperidine

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3802417
  • UNII-Q153V49P3Z
  • AKOS015896476
  • DTXSID60166035
  • CHEMBL270190
  • CHEBI:135686
  • SCHEMBL49578

Physico-Chemical properties

IUPAC name2-[[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanoyl]amino]acetic acid
Molecular formulaC25H32N2O4
Molecular weight424.533
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity124.96
LogP3.4
Topological polar surface area89.9

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.