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MedKoo Cat#: 319760 | Name: Edivoxetine

Description:

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

Edivoxetine, also known as LY2216684, is is a selective norepinephrine reuptake inhibitor under development for attention-deficit hyperactivity disorder (ADHD) and as an antidepressant treatment. It was in phase III clinical trials, in 2012, for major depressive disorder, but failed to get approval.

Chemical Structure

Edivoxetine
Edivoxetine
CAS#1194508-25-2 (free base)

Theoretical Analysis

MedKoo Cat#: 319760

Name: Edivoxetine

CAS#: 1194508-25-2 (free base)

Chemical Formula: C18H26FNO4

Exact Mass: 339.1846

Molecular Weight: 339.41

Elemental Analysis: C, 63.70; H, 7.72; F, 5.60; N, 4.13; O, 18.86

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Related CAS #
1194374-05-4 (HCl) 1194508-25-2 (free base)
Synonym
LY2216684; LY-2216684; LY 2216684; Edivoxetine; Edivoxetina
IUPAC/Chemical Name
(R)-2-(5-fluoro-2-methoxyphenyl)-1-((S)-morpholin-2-yl)-1-(tetrahydro-2H-pyran-4-yl)ethan-1-ol
InChi Key
CPBHSHYQQLFAPW-ZWKOTPCHSA-N
InChi Code
InChI=1S/C18H26FNO4/c1-22-16-3-2-15(19)10-13(16)11-18(21,14-4-7-23-8-5-14)17-12-20-6-9-24-17/h2-3,10,14,17,20-21H,4-9,11-12H2,1H3/t17-,18+/m0/s1
SMILES Code
O[C@@](C1CCOCC1)(CC2=CC(F)=CC=C2OC)[C@@H]3CNCCO3
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
Related CAS# 1194508-25-2 (Edivoxetine) 1194374-05-4 (Edivoxetine hydrochloride)

Preparing Stock Solutions

The following data is based on the product molecular weight 339.41 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.

Recalculate based on batch purity %
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: Markowitz JS, Brinda BJ. A pharmacokinetic evaluation of oral edivoxetine hydrochloride for the treatment of attention deficit-hyperactivity disorder. Expert Opin Drug Metab Toxicol. 2014 Sep;10(9):1289-99. doi: 10.1517/17425255.2014.939955. Epub 2014 Jul 14. PMID: 25019201. 2: Oakes TM, Dellva MA, Waterman K, Greenbaum M, Poppe C, Goldberger C, Ahl J, Perahia DG. Edivoxetine compared to placebo as adjunctive therapy to selective serotonin reuptake inhibitors in the prevention of symptom re-emergence in major depressive disorder. Curr Med Res Opin. 2015 Jun;31(6):1179-89. doi: 10.1185/03007995.2015.1037732. Epub 2015 May 6. PMID: 25894953. 3: Lin DY, Kratochvil CJ, Xu W, Jin L, D'Souza DN, Kielbasa W, Allen AJ. A randomized trial of edivoxetine in pediatric patients with attention- deficit/hyperactivity disorder. J Child Adolesc Psychopharmacol. 2014 May;24(4):190-200. doi: 10.1089/cap.2013.0043. PMID: 24840045; PMCID: PMC4026219. 4: Kielbasa W, Quinlan T, Jin L, Xu W, Lachno DR, Dean RA, Allen AJ. Pharmacokinetics and pharmacodynamics of edivoxetine (LY2216684), a norepinephrine reuptake inhibitor, in pediatric patients with attention- deficit/hyperactivity disorder. J Child Adolesc Psychopharmacol. 2012 Aug;22(4):269-76. doi: 10.1089/cap.2011.0151. Epub 2012 Jul 31. PMID: 22849510. 5: Nery ESM, Bangs M, Liu P, Ahl J, Perahia D. Long-Term, Open-Label, Safety Study of Edivoxetine Monotherapy in Children and Adolescents with Attention- Deficit/Hyperactivity Disorder. J Child Adolesc Psychopharmacol. 2017 Oct;27(8):700-707. doi: 10.1089/cap.2016.0110. Epub 2017 Apr 12. PMID: 28402139. 6: Martinez JM, Ferguson MB, Pangallo BA, Oakes TM, Sparks J, Dellva MA, Zhang Q, Liu P, Bangs M, Ahl J, Goldberger C. Safety and tolerability of edivoxetine as adjunctive treatment to selective serotonin reuptake inhibitor antidepressants for patients with major depressive disorder. Drugs Context. 2015 May 13;4:212279. doi: 10.7573/dic.212279. PMID: 26005493; PMCID: PMC4434861. 7: Ball SG, Ferguson MB, Martinez JM, Pangallo BA, Nery ES, Dellva MA, Sparks J, Zhang Q, Liu P, Bangs M, Goldberger C. Efficacy outcomes from 3 clinical trials of edivoxetine as adjunctive treatment for patients with major depressive disorder who are partial responders to selective serotonin reuptake inhibitor treatment. J Clin Psychiatry. 2016 May;77(5):635-42. doi: 10.4088/JCP.14m09619. PMID: 27035159. 8: Padilha SCOS, Virtuoso S, Tonin FS, Borba HHL, Pontarolo R. Efficacy and safety of drugs for attention deficit hyperactivity disorder in children and adolescents: a network meta-analysis. Eur Child Adolesc Psychiatry. 2018 Oct;27(10):1335-1345. doi: 10.1007/s00787-018-1125-0. Epub 2018 Feb 19. PMID: 29460165. 9: Ball S, Dellva MA, D'Souza DN, Marangell LB, Russell JM, Goldberger C. A double-blind, placebo-controlled study of edivoxetine as an adjunctive treatment for patients with major depressive disorder who are partial responders to selective serotonin reuptake inhibitor treatment. J Affect Disord. 2014;167:215-23. doi: 10.1016/j.jad.2014.06.006. Epub 2014 Jun 14. PMID: 24995890. 10: Hoaglund Hyzer CS, Williamson ML, Jansen PJ, Kopach ME, Scherer RB, Baertschi SW. Mechanistic Studies of the N-formylation of Edivoxetine, a Secondary Amine-Containing Drug, in a Solid Oral Dosage Form. J Pharm Sci. 2017 May;106(5):1218-1238. doi: 10.1016/j.xphs.2017.01.026. Epub 2017 Feb 1. PMID: 28159638. 11: Jin L, Xu W, Krefetz D, Gruener D, Kielbasa W, Tauscher-Wisniewski S, Allen AJ. Clinical outcomes from an open-label study of edivoxetine use in pediatric patients with attention-deficit/hyperactivity disorder. J Child Adolesc Psychopharmacol. 2013 Apr;23(3):200-7. doi: 10.1089/cap.2012.0016. PMID: 23607409. 12: Kielbasa W, Pan A, Pereira A. A pharmacokinetic/pharmacodynamic investigation: assessment of edivoxetine and atomoxetine on systemic and central 3,4-dihydroxyphenylglycol, a biochemical marker for norepinephrine transporter inhibition. Eur Neuropsychopharmacol. 2015 Mar;25(3):377-85. doi: 10.1016/j.euroneuro.2014.12.009. Epub 2015 Jan 5. PMID: 25637266. 13: Ball SG, Atkinson S, Sparks J, Bangs M, Goldberger C, Dubé S. Long-Term, Open-Label, Safety Study of Edivoxetine 12 to 18 mg Once Daily as Adjunctive Treatment for Patients With Major Depressive Disorder Who Are Partial Responders to Selective Serotonin Reuptake Inhibitor Treatment. J Clin Psychopharmacol. 2015 Jun;35(3):266-72. doi: 10.1097/JCP.0000000000000302. PMID: 25815754. 14: Kielbasa W, Lobo E. Pharmacodynamics of norepinephrine reuptake inhibition: Modeling the peripheral and central effects of atomoxetine, duloxetine, and edivoxetine on the biomarker 3,4-dihydroxyphenylglycol in humans. J Clin Pharmacol. 2015 Dec;55(12):1422-31. doi: 10.1002/jcph.551. Epub 2015 Jul 29. PMID: 26011686. 15: Wang SM, Han C, Pae CU. Criticisms of drugs in early development for the treatment of depression: what can be improved? Expert Opin Investig Drugs. 2015 Apr;24(4):445-53. doi: 10.1517/13543784.2014.985784. Epub 2014 Dec 20. PMID: 25529224. 16: Stauffer VL, Liu P, Goldberger C, Marangell LB, Nelson C, Gorwood P, Fava M. Is the Noradrenergic Symptom Cluster a Valid Construct in Adjunctive Treatment of Major Depressive Disorder? J Clin Psychiatry. 2017 Mar;78(3):317-323. doi: 10.4088/JCP.15m09972. PMID: 27685842. 17: Kielbasa W, Tesfaye E, Luffer-Atlas D, Mitchell MI, Turik MA. The effect of hepatic or renal impairment on the pharmacokinetics of edivoxetine, a selective norepinephrine transporter reuptake inhibitor. Eur J Clin Pharmacol. 2013 Dec;69(12):2011-9. doi: 10.1007/s00228-013-1572-y. Epub 2013 Aug 17. PMID: 23955175; PMCID: PMC3832778. 18: Hoaglund Hyzer CS, Fadda HM, Rodriguez JO, Aburub A. Leveraging BCS in Development: A Case Study. Mol Pharm. 2015 Oct 5;12(10):3685-90. doi: 10.1021/acs.molpharmaceut.5b00450. Epub 2015 Sep 17. PMID: 26365521. 19: Naguy A, Pridmore S, Alwetayan S, Elsori D, Alamiri B. ADHD-A Clinician's Bird's Eye View of Current Status and New Vistas! Psychopharmacol Bull. 2023 Feb 28;53(1):46-54. PMID: 36873919; PMCID: PMC9981341. 20: Weiller E, Weiss C, Watling CP, Edge C, Hobart M, Eriksson H, Fava M. Functioning outcomes with adjunctive treatments for major depressive disorder: a systematic review of randomized placebo-controlled studies. Neuropsychiatr Dis Treat. 2017 Dec 29;14:103-115. doi: 10.2147/NDT.S146840. PMID: 29343962; PMCID: PMC5751804.

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