CHEBI:85980 - eluxadoline

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ChEBI Name eluxadoline
ChEBI ID CHEBI:85980
Definition An amino acid amide obtained by the formal condensation of the carboxy group of 4-carbamoyl-2,6-dimethyl-L-phenylalanine with the secondary amino group of 2-methoxy-5-({[(1S)-1-(4-phenylimidazol-2-yl)ethyl]amino}methyl)benzoic acid. It has mixed opioid receptor activity and is used for treatment of irritable bowel syndrome with diarrhoea.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C32H35N5O5
Net Charge 0
Average Mass 569.65080
Monoisotopic Mass 569.26382
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
InChIKey QFNHIDANIVGXPE-FNZWTVRRSA-N
SMILES COc1ccc(CN([C@@H](C)c2nc(c[nH]2)-c2ccccc2)C(=O)[C@@H](N)Cc2c(C)cc(cc2C)C(N)=O)cc1C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
delta-opioid receptor antagonist
A compound that exhibits antagonist activity at the delta-opioid receptor.
kappa-opioid receptor agonist
A compound that exhibits agonist activity at the kappa-opioid receptor.
Application(s): mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
delta-opioid receptor antagonist
A compound that exhibits antagonist activity at the delta-opioid receptor.
kappa-opioid receptor agonist
A compound that exhibits agonist activity at the kappa-opioid receptor.
gastrointestinal drug
A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing eluxadoline (CHEBI:85980) has role δ-opioid receptor antagonist (CHEBI:59283)
eluxadoline (CHEBI:85980) has role κ-opioid receptor agonist (CHEBI:59282)
eluxadoline (CHEBI:85980) has role μ-opioid receptor agonist (CHEBI:55322)
eluxadoline (CHEBI:85980) has role gastrointestinal drug (CHEBI:55324)
eluxadoline (CHEBI:85980) is a L-phenylalanine derivative (CHEBI:84144)
eluxadoline (CHEBI:85980) is a amino acid amide (CHEBI:22475)
eluxadoline (CHEBI:85980) is a benzamides (CHEBI:22702)
eluxadoline (CHEBI:85980) is a imidazoles (CHEBI:24780)
eluxadoline (CHEBI:85980) is a methoxybenzoic acid (CHEBI:25238)
IUPAC Name
5-({(4-carbamoyl-2,6-dimethyl-L-phenylalanyl)[(1S)-1-(4-phenyl-1H-imidazol-2-yl)ethyl]amino}methyl)-2-methoxybenzoic acid
INN Source
eluxadoline ChemIDplus
Brand Name Source
Viberzi KEGG DRUG
Manual Xrefs Databases
5001 DrugCentral
D10403 KEGG DRUG
View more database links
Registry Numbers Types Sources
12390967 Reaxys Registry Number Reaxys
864821-90-9 CAS Registry Number ChemIDplus
864821-90-9 CAS Registry Number KEGG DRUG
Citations Waiting for Citations Types Sources
23583433 PubMed citation Europe PMC
25261794 PubMed citation Europe PMC
25491493 PubMed citation Europe PMC
Last Modified
22 February 2017