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2D Structure
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 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

2D Structure

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.