Eluxadoline | CAS#864821-90-9 | opioid receptor antagonist

MedKoo Cat#: 307109 | Name: Eluxadoline

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Eluxadoline is an orally-active drug approved for the treatment of diarrhea and abdominal pain in individuals with diarrhea-predominant irritable bowel syndrome (IBS-D). Eluxadoline is a μ- and κ-opioid receptor agonist and δ-opioid receptor antagonist that acts locally in the enteric nervous system, possibly decreasing adverse effects on the central nervous system. This product is discontinued (DEA Schedule IV).

Chemical Structure

Eluxadoline

CAS#864821-90-9 (free base)

Theoretical Analysis

MedKoo Cat#: 307109

Name: Eluxadoline

CAS#: 864821-90-9 (free base)

Chemical Formula: C32H35N5O5

Exact Mass: 569.2638

Molecular Weight: 569.66

Elemental Analysis: C, 67.47; H, 6.19; N, 12.29; O, 14.04

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Related CAS #

864825-13-8 (HCl) 864821-90-9 (free base)

Synonym

JNJ-27018966; JNJ27018966; JNJ 27018966; Eluxadoline, brand name: Viberzi.

IUPAC/Chemical Name

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

InChi Key

QFNHIDANIVGXPE-FNZWTVRRSA-N

InChi Code

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

SMILES Code

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

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, not in water

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 569.66 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Adler AI. NICE guidance on eluxadoline for treating irritable bowel syndrome with diarrhoea. Lancet Gastroenterol Hepatol. 2017 Nov;2(11):779-780. doi: 10.1016/S2468-1253(17)30267-4. Epub 2017 Aug 31. PubMed PMID: 31787228. 2: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012-. Available from http://www.ncbi.nlm.nih.gov/books/NBK548868/ PubMed PMID: 31644175. 3: Shahid Z, Packard E, Groff A, Jain R. Eluxadoline-induced pancreatitis occurring in an adult man without a prior cholecystectomy. BMJ Case Rep. 2019 Aug 28;12(8). pii: e231185. doi: 10.1136/bcr-2019-231185. PubMed PMID: 31466958. 4: Brenner DM, Sayuk GS, Gutman CR, Jo E, Elmes SJR, Liu LWC, Cash BD. Efficacy and Safety of Eluxadoline in Patients With Irritable Bowel Syndrome With Diarrhea Who Report Inadequate Symptom Control With Loperamide: RELIEF Phase 4 Study. Am J Gastroenterol. 2019 Sep;114(9):1502-1511. doi: 10.14309/ajg.0000000000000327. PubMed PMID: 31356229; PubMed Central PMCID: PMC6738625. 5: Lacy BE, Harris LA, Chang L, Lucak S, Gutman C, Dove LS, Covington PS, Lembo A. Impact of patient and disease characteristics on the efficacy and safety of eluxadoline for IBS-D: a subgroup analysis of phase III trials. Therap Adv Gastroenterol. 2019 Apr 15;12:1756284819841290. doi: 10.1177/1756284819841290. eCollection 2019. PubMed PMID: 31019552; PubMed Central PMCID: PMC6466471. 6: Lai SW. Safety of Eluxadoline Use. Am J Gastroenterol. 2019 Jul;114(7):1176-1177. doi: 10.14309/ajg.0000000000000205. PubMed PMID: 30920418. 7: Khetpal N, Yadav L, Khalid S, Kumar R. Eluxadoline-induced Recurrent Pancreatitis in a Young Female without a Gallbladder: A Case Report and Literature Review. Cureus. 2018 Dec 18;10(12):e3747. doi: 10.7759/cureus.3747. PubMed PMID: 30820368; PubMed Central PMCID: PMC6389028. 8: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006-. Available from http://www.ncbi.nlm.nih.gov/books/NBK536690/ PubMed PMID: 30694622. 9: Garcia-Gonzalez F, Faghih M, Singh V. Letter: eluxadoline-associated acute pancreatitis-myth or reality? Aliment Pharmacol Ther. 2018 Aug;48(4):490-491. doi: 10.1111/apt.14846. PubMed PMID: 30588698. 10: Harinstein L, Wu E, Brinker A. Letter: eluxadoline-associated acute pancreatitis-myth or reality? Authors' reply. Aliment Pharmacol Ther. 2018 Aug;48(4):491-492. doi: 10.1111/apt.14851. PubMed PMID: 30588693. 11: Dodda S, Makula A, Polagani SR, Kandhagatla RN. High sensitive LC-MS/MS method for estimation of eluxadoline in human plasma and its application to pharmacokinetic study. J Pharm Biomed Anal. 2019 Feb 20;165:65-72. doi: 10.1016/j.jpba.2018.11.056. Epub 2018 Nov 24. PubMed PMID: 30502553. 12: Abel JL, Carson RT, Andrae DA. The impact of treatment with eluxadoline on health-related quality of life among adult patients with irritable bowel syndrome with diarrhea. Qual Life Res. 2019 Feb;28(2):369-377. doi: 10.1007/s11136-018-2008-z. Epub 2018 Sep 28. PubMed PMID: 30267294; PubMed Central PMCID: PMC6373309. 13: Bonifacio L, Hunt TL, McIntyre G, Dove LS, Covington PS. Evaluation of Eluxadoline Effect on Cardiac Repolarization. Clin Pharmacol Drug Dev. 2018 Sep;7(7):727-736. doi: 10.1002/cpdd.453. Epub 2018 Apr 16. PubMed PMID: 29659201; PubMed Central PMCID: PMC6175186. 14: Coté GA. Editorial: the sphincter of Oddi strikes again-eluxadoline illuminates a controversial mechanism for the pathogenesis of acute pancreatitis. Aliment Pharmacol Ther. 2018 May;47(9):1324-1325. doi: 10.1111/apt.14596. PubMed PMID: 29644734. 15: Brenner DM, Dove LS, Andrae DA, Covington PS, Gutman C, Chey WD. Radar plots: A novel modality for displaying disparate data on the efficacy of eluxadoline for the treatment of irritable bowel syndrome with diarrhea. Neurogastroenterol Motil. 2018 Mar 25:e13331. doi: 10.1111/nmo.13331. [Epub ahead of print] PubMed PMID: 29575372. 16: Harinstein L, Wu E, Brinker A. Postmarketing cases of eluxadoline-associated pancreatitis in patients with or without a gallbladder. Aliment Pharmacol Ther. 2018 Mar;47(6):809-815. doi: 10.1111/apt.14504. Epub 2018 Jan 19. PubMed PMID: 29349789. 17: Anwer MK, Al-Shdefat R, Ezzeldin E, Alshahrani SM, Alshetaili AS, Iqbal M. Preparation, Evaluation and Bioavailability Studies of Eudragit Coated PLGA Nanoparticles for Sustained Release of Eluxadoline for the Treatment of Irritable Bowel Syndrome. Front Pharmacol. 2017 Nov 20;8:844. doi: 10.3389/fphar.2017.00844. eCollection 2017. PubMed PMID: 29209215; PubMed Central PMCID: PMC5702012. 18: Chedid V, Vijayvargiya P, Camilleri M. Advantages and Limitations of the Federal Adverse Events Reporting System in Assessing Adverse Event Reporting for Eluxadoline. Clin Gastroenterol Hepatol. 2018 Mar;16(3):336-338. doi: 10.1016/j.cgh.2017.11.025. Epub 2017 Nov 16. PubMed PMID: 29155353; PubMed Central PMCID: PMC5816691. 19: Iqbal M, Ezzeldin E, Al-Rashood KA, Al-Shdefat R, Anwer MK. High throughput μ-SPE based elution coupled with UPLC-MS/MS for determination of eluxadoline in plasma sample: Application in pharmacokinetic characterization of PLGA nanoparticle formulations in rats. J Pharm Biomed Anal. 2018 Feb 5;149:172-178. doi: 10.1016/j.jpba.2017.10.024. Epub 2017 Oct 28. PubMed PMID: 29121571. 20: Barshop K, Staller K. Eluxadoline in irritable bowel syndrome with diarrhea: rationale, evidence and place in therapy. Ther Adv Chronic Dis. 2017 Nov;8(11):153-160. doi: 10.1177/2040622317714389. Epub 2017 Jun 21. Review. PubMed PMID: 29090081; PubMed Central PMCID: PMC5638229.