eluxadoline   

GtoPdb Ligand ID: 7691

Synonyms: JNJ-27018966 | Truberzi®
eluxadoline is an approved drug (FDA (2015), EMA (2016))
Compound class: Synthetic organic
Comment: Eluxadoline is a first-in-class, locally-acting dual μ-opioid receptor agonist and δ-opioid receptor antagonist [1-2].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 164.63
Molecular weight 569.26
XLogP 3.86
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES COc1ccc(cc1C(=O)O)CN(C(c1ncc([nH]1)c1ccccc1)C)C(=O)C(Cc1c(C)cc(cc1C)C(=O)N)N
Isomeric SMILES COc1ccc(cc1C(=O)O)CN([C@H](c1ncc([nH]1)c1ccccc1)C)C(=O)[C@H](Cc1c(C)cc(cc1C)C(=O)N)N
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
InChI Key QFNHIDANIVGXPE-FNZWTVRRSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2015), EMA (2016))
IUPAC Name
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
International Nonproprietary Names
INN number INN
9749 eluxadoline
Synonyms
JNJ-27018966 | Truberzi®
Database Links
CAS Registry No. 864821-90-9
ChEMBL Ligand CHEMBL2159122
DrugCentral Ligand 5001
GtoPdb PubChem SID 223366025
PubChem CID 11250029
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Wikipedia Eluxadoline