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    Chemistry

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    Also known as: 864821-90-9, Viberzi, Truberzi, Jnj-27018966, Eluxadoline [usan], Jnj 27018966
    Molecular Formula
    C32H35N5O5
    Molecular Weight
    569.6  g/mol
    InChI Key
    QFNHIDANIVGXPE-FNZWTVRRSA-N
    FDA UNII
    45TPJ4MBQ1
    Eluxadoline
    Eluxadoline is a mixed mu-opioid receptor agonist, kappa-opioid receptor agonist, and a-delta opioid receptor antagonist indicated for use in diarrhea-predominant irritable bowel syndrome (IBS-D). The mu-, kappa-, and delta-opioid receptors mediate endogenous and exogenous opioid response in the central nervous system and peripherally in the gastrointestinal system. Agonism of peripheral mu-opioid receptors results in reduced colonic motility, while antagonism of central delta-opioid receptors results in improved analgesia, making eluxadoline usable for the symptoms of both pain and diarrhea characteristic of IBS-D. Marketed under the tradename Viberzi (FDA), eluxadoline is an antimotility agent that decreases bowel contractions, inhibits colonic transit, and reduces uid/ion secretion resulting in improved symptoms of abdominal pain and reductions in the Bristol Stool Scale.
    Eluxadoline is a mu-Opioid Receptor Agonist. The mechanism of action of eluxadoline is as an Opioid mu-Receptor Agonist.
    1 2D Structure

    Eluxadoline

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[[[(2S)-2-amino-3-(4-carbamoyl-2,6-dimethylphenyl)propanoyl]-[(1S)-1-(5-phenyl-1H-imidazol-2-yl)ethyl]amino]methyl]-2-methoxybenzoic acid
    2.1.2 InChI
    InChI=1S/C32H35N5O5/c1-18-12-23(29(34)38)13-19(2)24(18)15-26(33)31(39)37(17-21-10-11-28(42-4)25(14-21)32(40)41)20(3)30-35-16-27(36-30)22-8-6-5-7-9-22/h5-14,16,20,26H,15,17,33H2,1-4H3,(H2,34,38)(H,35,36)(H,40,41)/t20-,26-/m0/s1
    2.1.3 InChI Key
    QFNHIDANIVGXPE-FNZWTVRRSA-N
    2.1.4 Canonical SMILES
    CC1=CC(=CC(=C1CC(C(=O)N(CC2=CC(=C(C=C2)OC)C(=O)O)C(C)C3=NC=C(N3)C4=CC=CC=C4)N)C)C(=O)N
    2.1.5 Isomeric SMILES
    CC1=CC(=CC(=C1C[C@@H](C(=O)N(CC2=CC(=C(C=C2)OC)C(=O)O)[C@@H](C)C3=NC=C(N3)C4=CC=CC=C4)N)C)C(=O)N
    2.2 Other Identifiers
    2.2.1 UNII
    45TPJ4MBQ1
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Viberzi

    2.3.2 Depositor-Supplied Synonyms

    1. 864821-90-9

    2. Viberzi

    3. Truberzi

    4. Jnj-27018966

    5. Eluxadoline [usan]

    6. Jnj 27018966

    7. 45tpj4mbq1

    8. Chembl2159122

    9. Chebi:85980

    10. 864821-90-9 (free Base)

    11. Eluxadoline (usan)

    12. 5-(((s)-2-amino-3-(4-carbamoyl-2,6-dimethylphenyl)-n-((s)-1-(5-phenyl-1h-imidazol-2-yl)ethyl)propanamido)methyl)-2-methoxybenzoic Acid

    13. 5-({(4-carbamoyl-2,6-dimethyl-l-phenylalanyl)[(1s)-1-(4-phenyl-1h-imidazol-2-yl)ethyl]amino}methyl)-2-methoxybenzoic Acid

    14. Benzoic Acid, 5-((((2s)-2-amino-3-(4-(aminocarbonyl)-2,6-dimethylphenyl)-1-oxopropyl)((1s)-1-(5-phenyl-1h-imidazol-2-yl)ethyl)amino)methyl)-2-methoxy-

    15. Eluxadoline [usan:inn]

    16. Unii-45tpj4mbq1

    17. Benzoic Acid, 5-[[[(2s)-2-amino-3-[4-(aminocarbonyl)-2,6-dimethylphenyl]-1-oxopropyl][(1s)-1-(5-phenyl-1h-imidazol-2-yl)ethyl]amino]methyl]-2-methoxy-

    18. Viberzi (tn)

    19. Eluxadoline [mi]

    20. Eluxadoline [inn]

    21. Eluxadoline [who-dd]

    22. Gtpl7691

    23. Dea No. 9725

    24. Eluxadoline [nflis-drug]

    25. Schembl12971682

    26. Schembl17950908

    27. Dtxsid70235589

    28. Eluxadoline [orange Book]

    29. Amy39829

    30. Ex-a1169

    31. Mfcd28386164

    32. Zinc14210876

    33. Akos030632800

    34. Ccg-270093

    35. Cs-3855

    36. Db09272

    37. Jnj27018966

    38. Ncgc00485958-01

    39. Ac-30329

    40. As-35135

    41. Hy-12247

    42. Ft-0701295

    43. J3.535.064k

    44. A14085

    45. D10403

    46. Q20539232

    47. 5-((((2s)-2-amino-3-(4-carbamoyl-2,6-dimethylphenyl)propanoyl)((1s)-1-(4-phenyl-1h-imidazol-2-yl)ethyl)amino(methyl)-2-methoxybenzoic Acid

    48. 5-(((s)-2-amino-3-(4-carbamoyl-2,6-dimethylphenyl)-n-((s)-1-(4-phenyl-1h-imidazol-2-yl)ethyl)propanamido)methyl)-2-methoxybenzoic Acid

    49. 5-((2-amino-3-(4-carbamoyl-2,6-dimethylphenyl)-n-(1-(5-phenyl-1h-imidazol-2-yl)ethyl)propanamido)methyl)-2-methoxybenzoic Acid

    50. 5-[[[(2s)-2-amino-3-(4-carbamoyl-2,6-dimethylphenyl)propanoyl]-[(1s)-1-(4-phenyl-3h-imidazol-2-yl)ethyl]amino]methyl]-2-methoxybenzoic Acid

    51. 5-[[[(2s)-2-amino-3-(4-carbamoyl-2,6-dimethylphenyl)propanoyl]-[(1s)-1-(5-phenyl-1h-imidazol-2-yl)ethyl]amino]methyl]-2-methoxybenzoic Acid

    2.4 Create Date
    2006-10-26
    3 Chemical and Physical Properties
    Molecular Weight 569.6 g/mol
    Molecular Formula C32H35N5O5
    XLogP30.9
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count11
    Exact Mass569.26381923 g/mol
    Monoisotopic Mass569.26381923 g/mol
    Topological Polar Surface Area165 Ų
    Heavy Atom Count42
    Formal Charge0
    Complexity917
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    For the treatment of irritable bowel syndrome with diarrhea (IBS-D).

    FDA Label

    Truberzi is indicated in adults for the treatment of irritable bowel syndrome with diarrhoea (IBS D).

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Gastrointestinal Agents

    Drugs used for their effects on the gastrointestinal system, as to control gastric acidity, regulate gastrointestinal motility and water flow, and improve digestion. (See all compounds classified as Gastrointestinal Agents.)

    5.2 FDA Pharmacological Classification
    5.2.1 Active Moiety
    ELUXADOLINE
    5.2.2 FDA UNII
    45TPJ4MBQ1
    5.2.3 Pharmacological Classes
    mu-Opioid Receptor Agonist [EPC]; Opioid mu-Receptor Agonists [MoA]
    5.3 ATC Code

    A07

    A - Alimentary tract and metabolism

    A07 - Antidiarrheals, intestinal antiinflammatory/antiinfective agents

    A07D - Antipropulsives

    A07DA - Antipropulsives

    A07DA06 - Eluxadoline

    5.4 Absorption, Distribution and Excretion

    Absorption

    The oral absorption of eluxadoline is poor - estimated to be 1.02%, this could be attributed to poor in vitro GI permeability, and its zwitterionic nature leading to a negatively charged molecule across the GI pH range.

    Route of Elimination

    82% excreted in feces, <1% excreted in urine.

    5.5 Metabolism/Metabolites

    The metabolism of eluxadoline is currently unclear, however evidence suggests limited glucoronidation forms an acyl glucuronide metabolite that is then excreted into urine.

    5.6 Biological Half-Life

    The mean plasma elimination half-life ranged from 3.7 hours to 6 hours.

    5.7 Mechanism of Action

    Eluxadoline is a mu-opioid receptor agonis, kappa opioid receptor agonist and a delta opioid receptor antagonist. Eluxadoline is used for diarrhea predominant IBS because it reduces intestinal contractility and normalizes stress-induced acceleration of upper GI transit. Antagonistic activity at the delta receptor minimizes the constipating effect usually seen by mu-opioid receptor agonists alone. Because of it's limited systemic bioavailability, there may be less side effects associated with the use of eluxadoline in comparison with other therapies used to treat diarrhea predominant IBS.

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    20-Mar-2023
    02-Sep-2024
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