ELUXADOLINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H35N5O5
Molecular Weight	569.6508
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(CN([C@@H](C)C2=NC(=CN2)C3=CC=CC=C3)C(=O)[C@@H](N)CC4=C(C)C=C(C=C4C)C(N)=O)C=C1C(O)=O

InChI

InChIKey=QFNHIDANIVGXPE-FNZWTVRRSA-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

HIDE SMILES / InChI

Molecular Formula	C32H35N5O5
Molecular Weight	569.6508
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Eluxadoline, an orally active mixed μ opioid receptor (μOR) agonist δ opioid receptor (δOR) antagonist. Eluxadoline normalizes gastrointestinal (GI) transit and defecation under conditions of novel environment stress or post-inflammatory altered GI function. Allergan (previously Actavis) is developing eluxadoline for the treatment of diarrhoea-predominant irritable bowel syndrome. The agent was originated by Janssen Pharmaceutica. Eluxadoline has been launched in the US under trade name VIBERZI (eluxadoline) tablets, while is at the preregistration stage in the EU.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Delta opioid receptor 64	Antagonist 2491	Irritable Bowel Syndrome	1.3 nM [Ki]
Mu opioid receptor 190	Agonist 2361	Irritable Bowel Syndrome	1.7 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Irritable Bowel Syndrome 57	Primary	Delta opioid receptor Mu opioid receptor	Approved 7883	VIBERZI

PubMed

Title	Date	PubMed
Identification of a dual δ OR antagonist/μ OR agonist as a potential therapeutic for diarrhea-predominant Irritable Bowel Syndrome (IBS-d).	2012 Jul 15	22695132
Modulation of gastrointestinal function by MuDelta, a mixed µ opioid receptor agonist/ µ opioid receptor antagonist.	2012 Nov	22671931
Molecular characterization of eluxadoline as a potential ligand targeting mu-delta opioid receptor heteromers.	2014 Dec 1	25261794
Eluxadoline: First Global Approval.	2015 Jul	26149369

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage in adults is 100 mg twice daily taken with food. • The recommended dosage is 75 mg twice daily taken with food in patients who: * do not have a gallbladder * are unable to tolerate the 100 mg dose * are receiving concomitant OATP1B1 inhibitors * have mild or moderate hepatic impairment • Discontinue VIBERZI in patients who develop severe constipation for more than 4 days • If a dose is missed, take the next dose at the regular time; do not take 2 doses at once

Route of Administration: Oral

In Vitro Use Guide

In the guinea pig isolated ileum, MuDelta (eluxadoline) reduced electrical field stimulation-evoked contractions similar to DAMGO, with Kis of 1.0 and 1.3 nM, respectively. ) In guinea pig isolated proximal colon, MuDelta (eluxadoline) had weak k opioid receptor agonist activity compared with the k opioid receptor agonist ICI 204 448, with IC50 = 1.6 mM and 1.7 nM, respectively

Substance Class	Chemical Created by `admin` on `Mon Oct 21 21:39:04 UTC 2019` Edited by `admin` on `Mon Oct 21 21:39:04 UTC 2019`
Record UNII	45TPJ4MBQ1
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

ELUXADOLINE

Official Name

English

VIBERZI

Brand Name

English

JNJ-27018966

Code

English

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-

Common Name

English

ELUXADOLINE [USAN]

Common Name

English

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

Systematic Name

English

ELUXADOLINE [WHO-DD]

Common Name

English

ELUXADOLINE [INN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

A07DA06