Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00226)
Name
Eluxadoline
Synonyms    Click to Show/Hide the Synonyms of This API
Eluxadoline; 864821-90-9; Viberzi; truberzi; JNJ-27018966; UNII-45TPJ4MBQ1; 45TPJ4MBQ1; CHEMBL2159122; CHEBI:85980; 864821-90-9 (free base); 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; 5-({(4-carbamoyl-2,6-dimethyl-L-phenylalanyl)[(1S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl]amino}methyl)-2-methoxybenzoic acid; JNJ 27018966; Eluxadoline [USAN:INN]; Viberzi (TN); Eluxadoline (USAN); GTPL7691; DEA No. 9725; SCHEMBL12971682; SCHEMBL17950908; DTXSID70235589; EX-A1169; MFCD28386164; ZINC14210876; AKOS030632800; CCG-270093; CS-3855; DB09272; SB17335; NCGC00485958-01; AC-30329; AS-35135; HY-12247; FT-0701295; J3.535.064K; A14085; D10403; Q20539232; 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; 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; 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; 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-
Clinical Status
Approved
Disease Indication Irritable bowel syndrome ICD-11: DD91 [1]
PubChem CID
11250029
Formula
C32H35N5O5
Canonical 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
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
InChIKey
QFNHIDANIVGXPE-FNZWTVRRSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=11250029"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 569.6 Topological Polar Surface Area 165
XlogP 0.9 Complexity 917
Heavy Atom Count 42 Rotatable Bond Count 11
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 7
Full List of Drug Formulations (DFMs) Containing This API
          Eluxadoline 100 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Mannitol; Ferric oxide red; Ferric oxide yellow; Talc; Titanium dioxide; Crospovidone; Polyvinyl alcohol; Silicon dioxide; Cellulose, microcrystalline; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Allergan
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
          Eluxadoline 75 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Magnesium stearate; Mannitol; Ferric oxide red; Ferric oxide yellow; Talc; Titanium dioxide; Crospovidone; Polyvinyl alcohol; Silicon dioxide; Cellulose, microcrystalline; Polyethylene glycols
                   Dosage Form Oral Tablet
                   Company Allergan
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [2]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [3]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Crospovidone DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [4]
References
1 FDA label for approved eluxadoline from the official website of the U.S. Food and Drug Administration.
2 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
3 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
4 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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