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Alvimopan

July 24, 2017
Common Name

Alvimopan Description

Alvimopan is only found in individuals that have used or taken this drug. It is a peripherally selective opioid antagonist being investigated for the treatment of various gastrointestinal diseases and disorders.Alvimopan competitively binds to mu-opioid receptor in the gastrointestinal tract. Unlike methylnaltrexone (another peripherally acting mu-receptor antagonist) that bears a quaternary amine, alvimopan owes its selectivity for peripheral receptors to its kinetics. Alvimopan binds to peripheral mu-receptors with a Ki of 0.2 ng/mL and dissociates slower than most other ligands. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source ADL 8-2698EnteregChEMBL ADL 8-2698HMDB Anhydrous alvimopanMeSH trans-3,4-Dimethyl-4-(3-hydroxyphenyl) piperidineMeSH EnteregMeSH Alvimopan anhydrousMeSH

Chemical Formlia

C25H32N2O4 Average Molecliar Weight

424.5326 Monoisotopic Molecliar Weight

424.236207522 IUPAC Name

2-[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanamido]acetic acid Traditional Name

alvimopan CAS Registry Number

156053-89-3 SMILES

C[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 Identifier

InChI=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 Key

UPNUIXSCZBYVBB-JVFUWBCBSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Peptidomimetics Direct Parent

Hybrid peptides Alternative Parents

  • N-acyl-alpha amino acids
  • Phenylpiperidines
  • Beta amino acids and derivatives
  • 1-hydroxy-2-unsubstituted benzenoids
  • 1-hydroxy-4-unsubstituted benzenoids
  • Aralkylamines
  • Fatty amides
  • Benzene and substituted derivatives
  • Trialkylamines
  • Secondary carboxylic acid amides
  • Amino acids
  • Monocarboxylic acids and derivatives
  • Azacyclic compounds
  • Carboxylic acids
  • Hydrocarbon derivatives
  • Organic oxides
  • Organopnictogen compounds
  • Carbonyl compounds

    • 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

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

    Not Available Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Opiate Antagonists

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility8.34e-03 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.0083 mg/mLALOGPS logP3.25ALOGPS logP0.82ChemAxon logS-4.7ALOGPS pKa (Strongest Acidic)3.71ChemAxon pKa (Strongest Basic)10.66ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area89.87 Å2ChemAxon Rotatable Bond Count8ChemAxon Refractivity120.56 m3·mol-1ChemAxon Polarizability46.77 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Alvimopan Action PathwaySMP00685Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06274

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06274

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB06274 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    4589864 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Alvimopan NuGOwiki Link

    HMDB15631 Metagene Link

    HMDB15631 METLIN ID

    Not Available PubChem Compound

    5488548 PDB ID

    Not Available ChEBI ID

    535293

    Product: Danofloxacin (mesylate)

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. [No authors listed] [PubMed:18373729 ]
    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. [PubMed:23066346 ]
    3. FDA [Link]

    Enzymes

    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Highly stereoselective. receptor for enkephalins
    Gene Name:
    OPRD1
    Uniprot ID:
    P41143
    Molecular weight:
    40412.3
    References
    1. Neary P, Delaney CP: Alvimopan. Expert Opin Investig Drugs. 2005 Apr;14(4):479-88. [PubMed:15882122 ]
    2. Beattie DT, Cheruvu M, Mai N, OKeefe M, Johnson-Rabidoux S, Peterson C, Kaufman E, Vickery R: The in vitro pharmacology of the peripherally restricted opioid receptor antagonists, alvimopan, ADL 08-0011 and methylnaltrexone. Naunyn Schmiedebergs Arch Pharmacol. 2007 May;375(3):205-20. Epub 2007 Mar 6. [PubMed:17340127 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for beta-endorphin
    Gene Name:
    OPRM1
    Uniprot ID:
    P35372
    Molecular weight:
    44778.9
    References
    1. Kraft MD: Emerging pharmacologic options for treating postoperative ileus. Am J Health Syst Pharm. 2007 Oct 15;64(20 Suppl 13):S13-20. [PubMed:17909271 ]
    2. [No authors listed] [PubMed:18373729 ]
    3. Saufl NM, Strzyzewski N: Nurses are everywhere: a practical perspective on the surgical team in managing postoperative ileus. J Perianesth Nurs. 2006 Apr;21(2A Suppl):S24-9. [PubMed:16597533 ]
    4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    5. Neary P, Delaney CP: Alvimopan. Expert Opin Investig Drugs. 2005 Apr;14(4):479-88. [PubMed:15882122 ]
    6. Schmidt WK: Alvimopan* (ADL 8-2698) is a novel peripheral opioid antagonist. Am J Surg. 2001 Nov;182(5A Suppl):27S-38S. [PubMed:11755894 ]
    General function:
    Involved in G-protein coupled receptor protein signaling pathway
    Specific function:
    Inhibits neurotransmitter release by reducing calcium ion currents and increasing potassium ion conductance. Receptor for dynorphins. May play a role in arousal and regulation of autonomic and neuroendocrine functions
    Gene Name:
    OPRK1
    Uniprot ID:
    P41145
    Molecular weight:
    42644.7
    References
    1. Beattie DT, Cheruvu M, Mai N, OKeefe M, Johnson-Rabidoux S, Peterson C, Kaufman E, Vickery R: The in vitro pharmacology of the peripherally restricted opioid receptor antagonists, alvimopan, ADL 08-0011 and methylnaltrexone. Naunyn Schmiedebergs Arch Pharmacol. 2007 May;375(3):205-20. Epub 2007 Mar 6. [PubMed:17340127 ]
    2. Neary P, Delaney CP: Alvimopan. Expert Opin Investig Drugs. 2005 Apr;14(4):479-88. [PubMed:15882122 ]

    PMID: 12721338

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