Alvimopan (CED0009657)

Record Information
Version1.0
Creation Date2016-05-25 18:29:28 UTC
Update Date2026-08-22 05:21:57 UTC
Accession NumberCHEM022351
Identification
Common NameAlvimopan
ClassSmall Molecule
Description
Alvimopan is an organic compound with the formula C25H32N2O4 and an average molecular weight of 424.53 g/mol. Alvimopan belongs to the hybrid peptides, a subclass of peptidomimetics within the organic compounds. This compound is utilized within healthcare, pharmaceuticals, and veterinary products as a drug for constipation, with oral exposure being the recorded route of administration. In terms of protein targets, alvimopan acts as an antagonist of the Delta-type opioid receptor (OPRD1), the Kappa-type opioid receptor (OPRK1), and the Mu-type opioid receptor (OPRM1).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ADL 8-2698EnteregHMDB
ADL 8-2698HMDB
Anhydrous alvimopanHMDB
trans-3,4-Dimethyl-4-(3-hydroxyphenyl) piperidineHMDB
EnteregHMDB
Alvimopan anhydrousHMDB
Chemical FormulaC25H32N2O4
Average Molecular Mass424.533 g/mol
Monoisotopic Mass424.236 g/mol
CAS Registry Number156053-89-3
IUPAC NameNot Available
Traditional NameNot Available
SMILESC[C@H]1CN(C[C@H](CC2=CC=CC=C2)C(=O)NCC(O)=O)CC[C@@]1(C)C1=CC(O)=CC=C1
InChI IdentifierInChI=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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassHybrid peptides
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Phenylpiperidine
  • Beta amino acid or derivatives
  • Alpha-amino acid or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Piperidine
  • Fatty acyl
  • Fatty amide
  • Amino acid or derivatives
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0fr6-5947300000-a56d3fba4a79398cd53eNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0fkc-9030260000-07291dc02727a1b76e9cNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00b9-4135900000-cdd9dcd5c0e44a4d2c3aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-7659100000-c6c4baaf84ffc4a524ffNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ba-4921000000-1d5e9cec550e68fc676dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-0013900000-26c80cc1229d409f18b0Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0fk9-2389700000-5887ae4c83be056c9be4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-7690000000-04222ab40d4c3cdf96ddNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-0116900000-7e677f87932e437c28b8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056r-0179500000-9a36c62b4f259dfc6d00Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-1921000000-c9da581bb4acc528324aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00fr-0009800000-6c5de1cc3dd55967c60bNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00fr-4509100000-844a82b338df3daf6e8eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01b9-7975000000-248c5b20b32a461b463dNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
3933.0Log mg/kg[2200:7000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
253Drugs for constipationHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
3 pathways
Alvimopan Action Pathway
Alvimopan Action Pathway
Alvimopan Opioid Antagonist Action Pathway
Alvimopan Opioid Antagonist Action Pathway
Alvimopan Drug Metabolism Action Pathway
Alvimopan Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureKappa-type opioid receptorP41144Cavia porcellusPredicted (SEA)13.2344
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)17.9832
Delta-type opioid receptor structureClick to view 3D structureDelta-type opioid receptorP41143HumansPredicted (SEA)21.4085
Kappa-type opioid receptor structureClick to view 3D structureKappa-type opioid receptorP41145HumansPredicted (SEA)25.4567
Click to view 3D structureMu-type opioid receptorP33535Rattus norvegicusPredicted (SEA)55.9736
Click to view 3D structureMu-type opioid receptorP97266Cavia porcellusPredicted (SEA)104.707
Click to view 3D structureDelta-type opioid receptorP33533Rattus norvegicusPredicted (SEA)132.655
Voltage-dependent L-type calcium channel subunit alpha-1C structureClick to view 3D structureVoltage-dependent L-type calcium channel subunit alpha-1CQ13936HumansPredicted (SEA)3.97031
Click to view 3D structureNeprilysinP07861Rattus norvegicusPredicted (SEA)15.4141
Neprilysin structureClick to view 3D structureNeprilysinP08473HumansPredicted (SEA)19.3066
Click to view 3D structureNeprilysinP08049Oryctolagus cuniculusPredicted (SEA)35.5771
Click to view 3D structureKappa-type opioid receptorP34975Rattus norvegicusPredicted (SEA)150.638
Angiotensin-converting enzyme structureClick to view 3D structureAngiotensin-converting enzymeP12821HumansPredicted (SEA)60.0996
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)270.215
Click to view 3D structureAngiotensin-converting enzymeP47820Rattus norvegicusPredicted (SEA)35.11
Click to view 3D structure3-hydroxy-3-methylglutaryl-coenzyme A reductaseP09610Mesocricetus auratusPredicted (SEA)52.0811
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)961.049
Click to view 3D structureD(1A) dopamine receptorP18901Rattus norvegicusPredicted (SEA)146.746
Click to view 3D structureAngiotensin-converting enzymeP12822Oryctolagus cuniculusPredicted (SEA)57.842
Click to view 3D structureDelta-type opioid receptorP32300Mus musculusPredicted (SEA)280.102
Click to view 3D structureMu-type opioid receptorP42866Mus musculusPredicted (SEA)188.317
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)495.121
Aminopeptidase N structureClick to view 3D structureAminopeptidase NP15144HumansPredicted (SEA)133.979
Click to view 3D structureAminopeptidase NP15145Sus scrofaPredicted (SEA)83.2208
Solute carrier family 15 member 1 structureClick to view 3D structureSolute carrier family 15 member 1P46059HumansPredicted (SEA)48.3444
Concentrations
Not Available
External Links
DrugBank IDDB06274
HMDB IDHMDB0015631
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAlvimopan
Chemspider ID4589864
ChEBI ID535293
PubChem Compound ID5488548
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. [No authors listed]
2. Wang S, Shah N, Philip J, Caraccio T, Feuerman M, Malone B: Role of alvimopan (entereg) in gastrointestinal recovery and hospital length of stay after bowel resection. P T. 2012 Sep;37(9):518-25.
3. FDA: http://www.fda.gov/Safety/MedWatch/SafetyInformation/ucm194328.htm