U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ELUXADOLINE

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

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VIBERZI
PubMed

PubMed

TitleDatePubMed
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
Modulation of gastrointestinal function by MuDelta, a mixed µ opioid receptor agonist/ µ opioid receptor antagonist.
2012 Nov
Molecular characterization of eluxadoline as a potential ligand targeting mu-delta opioid receptor heteromers.
2014 Dec 1
Eluxadoline: First Global Approval.
2015 Jul
Patents

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
DASH   INN   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Mon Oct 21 21:39:04 UTC 2019 , Edited by admin on Mon Oct 21 21:39:04 UTC 2019
NDF-RT N0000191867
Created by admin on Mon Oct 21 21:39:04 UTC 2019 , Edited by admin on Mon Oct 21 21:39:04 UTC 2019
Code System Code Type Description
INN
9749
Created by admin on Mon Oct 21 21:39:04 UTC 2019 , Edited by admin on Mon Oct 21 21:39:04 UTC 2019
PRIMARY
CAS
864821-90-9
Created by admin on Mon Oct 21 21:39:04 UTC 2019 , Edited by admin on Mon Oct 21 21:39:04 UTC 2019
PRIMARY
WIKIPEDIA
Eluxadoline
Created by admin on Mon Oct 21 21:39:04 UTC 2019 , Edited by admin on Mon Oct 21 21:39:04 UTC 2019
PRIMARY
PUBCHEM
11250029
Created by admin on Mon Oct 21 21:39:04 UTC 2019 , Edited by admin on Mon Oct 21 21:39:04 UTC 2019
PRIMARY
IUPHAR
7691
Created by admin on Mon Oct 21 21:39:04 UTC 2019 , Edited by admin on Mon Oct 21 21:39:04 UTC 2019
PRIMARY
DRUG BANK
DB09272
Created by admin on Mon Oct 21 21:39:04 UTC 2019 , Edited by admin on Mon Oct 21 21:39:04 UTC 2019
PRIMARY
EVMPD
SUB175259
Created by admin on Mon Oct 21 21:39:04 UTC 2019 , Edited by admin on Mon Oct 21 21:39:04 UTC 2019
PRIMARY
ChEMBL
CHEMBL2159122
Created by admin on Mon Oct 21 21:39:04 UTC 2019 , Edited by admin on Mon Oct 21 21:39:04 UTC 2019
PRIMARY
EPA CompTox
864821-90-9
Created by admin on Mon Oct 21 21:39:04 UTC 2019 , Edited by admin on Mon Oct 21 21:39:04 UTC 2019
PRIMARY
NDF-RT
N0000191866
Created by admin on Mon Oct 21 21:39:04 UTC 2019 , Edited by admin on Mon Oct 21 21:39:04 UTC 2019
PRIMARY Opioid mu-Receptor Agonists [MoA]
RXCUI
1653781
Created by admin on Mon Oct 21 21:39:04 UTC 2019 , Edited by admin on Mon Oct 21 21:39:04 UTC 2019
PRIMARY RxNorm
Related Record Type Details
TRANSPORTER -> INHIBITOR
WEAK
TRANSPORTER -> SUBSTRATE
Based on in-vitro studies, eluxadoline appears to be a substrate for OAT3, OATP1B1, BSEP, and MRP2
METABOLIC ENZYME -> INHIBITOR
In an in-vitro study, eluxadoline appears to show time-dependent inhibition of CYP3A4 at 50 ?M, a concentration that can be achieved in the gut (Igut is estimated to be 700 ?M).
TRANSPORTER -> SUBSTRATE
Based on in-vitro studies, eluxadoline appears to be a substrate for OAT3, OATP1B1, BSEP, and MRP2
BINDER->LIGAND
BINDING
TRANSPORTER -> SUBSTRATE
Based on in-vitro studies, eluxadoline appears to be a substrate for OAT3, OATP1B1, BSEP, and MRP2
EXCRETED UNCHANGED
On average, 0.12% of the administered dose was recovered from urine up to 192 hours post-dose and 82% was recovered from feces up to 336 hours post-dose. The percentage of radioactivity excreted as unchanged drug vs. metabolites in urine and feces was not assessed in this study.
TRANSPORTER -> SUBSTRATE
Based on in-vitro studies, eluxadoline appears to be a substrate for OAT3, OATP1B1, BSEP, and MRP2
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Tmax PHARMACOKINETIC SINGLE DOSE ADMINISTRATION