EDIVOXETINE

EDIVOXETINE, LY 2216684

(1R)-2-(5-fluoro-2-methoxyphenyl)-1-[(2S)-morpholin-2-yl]-1-(oxan-4-yl)ethanol

UNII-3W9N3F4JOO, 1194508-25-2, Edivoxetine [USAN], Edivoxetine (USAN/INN), Edivoxetine [USAN:INN], 3W9N3F4JOO

Molecular Formula:C18H26FNO4

Molecular Weight:339.401743 g/mol

Edivoxetine (INN; LY-2216684) is a drug which acts as a selective norepinephrine reuptake inhibitor and is currently under development by Eli Lilly for attention-deficit hyperactivity disorder (ADHD) and as an antidepressant treatment.[1][2] It was in phase IIIclinical trials, in 2012, for major depressive disorder, but failed to get approval.[1][3]

Effectiveness

In a study published in 2010, edivoxetine failed to prove superiority over placebo, as measured by Hamilton Depression Rating Scale. However, effectiveness could be observed using the Self-Rated Quick Inventory of Depressive Symptomatology.[4]

In a study published in 2011, using the Montgomery-Åsberg Depression Rating Scale and the Sheehan Disability Scale, edivoxetine showed superiority over placebo, with higher response and remission rates.[5]

In December 2013, Eli Lilly announced that the clinical development of edivoxetine will be stopped due to lack of efficacy compared to SSRI alone in three separate clinical trials.[6]

Side effects

Side effects significantly associated with edivoxetine are headache, nausea, constipation, dry mouth and insomnia.[4]

The above mention studies report increases of the cardiac rhythm, and one also increases of diastolic and systolic blood pressures.[4][5]

Org. Process Res. Dev., Article ASAP

DOI: 10.1021/op5003825

http://pubs.acs.org/doi/abs/10.1021/op5003825

There is a growing trend in Ireland toward greater collaboration between academia and the pharmaceutical industry. This is an activity encouraged at a national policy level as a means of providing researchers from academic institutions the opportunity to gain important first-hand experience in a commercial research environment, while also providing industry access to expertise and resources to develop new and improved processes for timely medicines. The participating company benefits in terms of its growth, the evolution of its strategic research and development, and the creation of new knowledge that it can use to generate commercial advantage. The research institute benefits in terms of developing skill sets, intellectual property, and publications, in addition to access to identified current industry challenges. A case study is provided describing the collaborative partnership between a synthetic chemistry research team at University College Cork (UCC) and Eli Lilly and Company.

Anita R. Maguire * ,

Department of Chemistry and School of Pharmacy, Analytical and Biological Chemistry Research Facility, Synthesis and Solid State Pharmaceutical Centre,University College Cork, Cork, Ireland

E-mail: a.maguire@ucc.ie.

University College Cork

http://www.ucc.ie/en/support/senior-mgt/researchandinnovation/

http://chemweb.ucc.ie/people/amaguire.htm

SYSTEMATIC (IUPAC) NAME
(1R)-2-(5-fluoro-2-methoxyphenyl)-1-[(2S)-morpholin-2-yl]-1-(tetrahydro-2H-pyran-4-yl)ethanol
CLINICAL DATA
LEGAL STATUS	?
IDENTIFIERS
CAS NUMBER	1194508-25-2 1194374-05-4 (hydrochloride)
ATC CODE	None
PUBCHEM	CID 11186829
CHEMSPIDER	9361913
CHEMICAL DATA
FORMULA	C18H26FNO4
MOLECULAR MASS	339.402 g/mol

References

1.  Jun Yan (March 2012). “Pipeline for new antidepressants flowing slowly”. Psychiatric News (American Psychiatric Association) 47 (5): 1b-29. Retrieved 2012-04-27.
2.  “Statement on a nonproprietary name adopted by the USAN council – Edivoxetine”(Press release). American Medical Association. 2012. Retrieved 2012-04-12.
3.  Chancellor D (November 2011). “The depression market”. Nature Reviews. Drug Discovery 10 (11): 809–10. doi:10.1038/nrd3585. PMID 22037032.
4.  Dubé S, Dellva MA, Jones M, Kielbasa W, Padich R, Saha A, Rao P (April 2010). “A study of the effects of LY2216684, a selective norepinephrine reuptake inhibitor, in the treatment of major depression”. Journal of Psychiatric Research 44 (6): 356–363.doi:10.1016/j.jpsychires.2009.09.013. PMID 19909980.
5.  Pangallo P, Dellva MA, D’Souza DN, Essink B, Russell J, Goldberger C (June 2011).“A randomized, double-blind study comparing LY2216684 and placebo in the treatment of major depressive disorder”. Journal of Psychiatric Research 45 (6): 748–755. doi:10.1016/j.jpsychires.2011.03.014. PMID 21511276.
6.  https://investor.lilly.com/releasedetail.cfm?ReleaseID=811751

H-NMR spectral analysis

CAS NO. 1194508-25-2, (1R)-2-(5-fluoro-2-methoxyphenyl)-1-[(2S)-morpholin-2-yl]-1-(oxan-4-yl)ethanol H-NMR spectral analysis

C-NMR spectral analysis

CAS NO. 1194508-25-2, (1R)-2-(5-fluoro-2-methoxyphenyl)-1-[(2S)-morpholin-2-yl]-1-(oxan-4-yl)ethanol C-NMR spectral analysis

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